Identification

Name
Tamoxifen
Accession Number
DB00675  (APRD00123)
Type
Small Molecule
Groups
Approved
Description

One of the selective estrogen receptor modulators (SERM) with tissue-specific activities for the treatment and prevention of estrogen receptor positive breast cancer. Tamoxifen acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism, bone density, and cell proliferation in the endometrium. [PubChem]

Structure
Thumb
Synonyms
  • (Z)-2-(4-(1,2-Diphenyl-1-butenyl)phenoxy)-N,N-dimethylethanamine
  • (Z)-2-(Para-(1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethylamine
  • 1-P-beta-Dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • 1-Para-beta-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • Citofen
  • Crisafeno
  • Diemon
  • Istubol
  • Nourytam
  • Oncomox
  • Retaxim
  • Tamoxasta
  • Tamoxifen
  • Tamoxifène
  • Tamoxifene
  • Tamoxifeno
  • Tamoxifenum
  • trans-Tamoxifen
  • Valodex
  • Zemide
External IDs
ICI-46474 / ICI-47699
Product Ingredients
IngredientUNIICASInChI Key
Tamoxifen Citrate7FRV7310N654965-24-1FQZYTYWMLGAPFJ-OQKDUQJOSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-tamoxifenTablet10 mgOralDominion PharmacalNot applicable2016-10-25Canada
Dom-tamoxifenTablet20 mgOralDominion PharmacalNot applicableNot applicableCanada
Mylan-tamoxifenTablet20 mgOralMylan Pharmaceuticals1994-12-312017-01-09Canada
Mylan-tamoxifenTablet10 mgOralMylan Pharmaceuticals1994-12-312017-01-09Canada
Nolvadex Tab 10mgTablet10 mgOralAstra Zeneca1994-12-312003-04-01Canada
Nolvadex-D Tab 20mgTablet20 mgOralAstra Zeneca1995-12-31Not applicableCanada
Penta-tamoxifen TabletsTablet20 mgOralPentapharm Ltd.Not applicableNot applicableCanada
Penta-tamoxifen TabletsTablet10 mgOralPentapharm Ltd.Not applicableNot applicableCanada
PMS-tamoxifenTablet20 mgOralPharmascience Inc1998-12-012016-10-28Canada
PMS-tamoxifenTablet10 mgOralPharmascience Inc1998-12-012016-10-28Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tamox Tab 10mgTablet10 mgOralApotex Corporation1989-12-31Not applicableCanada
Apo-tamox Tab 20mgTablet20 mgOralApotex Corporation1989-12-31Not applicableCanada
Tamoxifen CitrateTablet20 mg/1OralA S Medication Solutions2011-08-152017-06-20Us
Tamoxifen CitrateTablet, film coated20 mg/1OralTeva2003-02-212019-02-28Us00093 0782 56 nlmimage10 392b1c88
Tamoxifen CitrateTablet, film coated10 mg/1OralPhysicians Total Care, Inc.1994-04-26Not applicableUs00093 0784 06 nlmimage10 610eb085
Tamoxifen CitrateTablet10 mg/1OralMylan Pharmaceuticals2003-02-20Not applicableUs
Tamoxifen CitrateTablet20 mg/1OralA S Medication Solutions2011-08-15Not applicableUs
Tamoxifen CitrateTablet10 mg/1OralAmerincan Health Packaging2015-03-31Not applicableUs
Tamoxifen CitrateTablet10 mg/1OralActavis Pharma Company2011-08-15Not applicableUs
Tamoxifen CitrateTablet, film coated10 mg/1OralMayne Pharma2016-08-03Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SoltamoxLiquid20 mg/10mLOralMidatech Pharma Us Inc.2005-10-29Not applicableUs
International/Other Brands
Adifen (Medicamerc) / Adopan (Sawai Seiyaku) / Apo-tamox / Bilem (Teva Int'l) / Caditam (Cadila) / Citofen / Crisafeno (LKM) / Doctamoxifene (Docpharma) / Ebefen (Ebewe) / Fenahex (Sandoz) / Gen-tamoxifen / Genox (Merck Serono) / Gynatam (Biogalenic) / Istubal (AstraZeneca) / Mammonex (CP Pharmaceuticals) / Neophedan (Aspen Pharmacare) / Noltam / Nolvadex (AstraZeneca) / Nolvadex-D (AstraZeneca) / Novofen (Remedica) / Oncomox (Sun) / Tadex (Orion) / Tamifen (Medochemie) / Tamizam (Mithra) / Tamofen (Sanofi-Aventis) / Tamone / Tamoneprin (Actavis) / Tamoplex (Pharmachemie) / Tamoxen (Ascent) / Tamoxilon (Celon) / Tamtero (Hetero) / Tecnotax (Zodiac) / Tomifen (Alkem) / Valodex / Zemide
Categories
UNII
094ZI81Y45
CAS number
10540-29-1
Weight
Average: 371.5146
Monoisotopic: 371.224914555
Chemical Formula
C26H29NO
InChI Key
NKANXQFJJICGDU-QPLCGJKRSA-N
InChI
InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
IUPAC Name
(2-{4-[(1Z)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine
SMILES
CC\C(=C(/C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1

Pharmacology

Indication

Tamoxifen is indicated for the treatment of metastatic breast cancer in women and men and ductal carcinoma in Situ.

Structured Indications
Pharmacodynamics

Tamoxifen belongs to a class of drugs called selective estrogen receptor modulators (SERMs), which have both estrogenic and antiestrogenic effects. Tamoxifen has the same nucleus as diethylstilbestrol but possesses an additional side chain (trans isomer) which accounts for its antiestrogenic activity.

Mechanism of action

Tamoxifen is a nonsteroidal agent that binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes. The prolonged binding of tamoxifen to the nuclear chromatin of these results in reduced DNA polymerase activity, impaired thymidine utilization, blockade of estradiol uptake, and decreased estrogen response. It is likely that tamoxifen interacts with other coactivators or corepressors in the tissue and binds with different estrogen receptors, ER-alpha or ER-beta, producing both estrogenic and antiestrogenic effects.

TargetActionsOrganism
AEstrogen receptor alpha
antagonist
agonist
Human
AEstrogen receptor beta
antagonist
agonist
Human
U3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseNot AvailableHuman
UProtein kinase CNot AvailableHuman
UAndrogen receptorNot AvailableHuman
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Human
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
UEstrogen-related receptor gammaNot AvailableHuman
USex hormone-binding globulinNot AvailableHuman
Absorption

When a single oral dose of 20 mg is given, the average peak plasma concentration (Cmax) is 40 ng/mL which occurred approximately 5 hours after dosing (Tmax). The Cmax of N-desmethyl tamoxifen is 15 ng/mL. Steady-state concentrations for tamoxifen is achieved in 4 weeks, while steady-state concentrations for N-desmethyl tamoxifen is achieved in 8 weeks.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic. Tamoxifen is extensively metabolized after oral administration. N-Desmethyl-tamoxifen is the major metabolite found in plasma. N-Desmethyl-tamoxifen's activity is similar to tamoxifen. 4-hydroxy-tamoxifen and a side chain primary alcohol derivative of tamoxifen have been identified as minor metabolites in plasma. 4-Hydroxy-tamoxifen formation is catalyzed mainly by cytochrome P450 (CYP) 2D6, and also by CYP2C9 and 3A4. At high tamoxifen concentrations, CYP2B6 also catalyzes 4-hydroxylation of the parent drug. 4-Hydroxy-tamoxifen possesses 30- to 100-times greater affinity for the estrogen receptor and 30- to 100-times greater potency at inhibiting estrogen-dependent cell proliferation compared to tamoxifen. It is also metabolized by flavin monooxygenases FMO1 and FMO3 to form tamoxifen-N-oxide.

Route of elimination

65% of the dose was excreted from the body over 2 weeks in which fecal excretion was the primary route of elimination. Tamoxifen is excreted mainly as polar conjugates, with unchanged drug and unconjugated metabolites accounting for less than 30% of the total fecal radioactivity.

Half life

The decline in tamoxifen plasma concentrations is biphasic with a terminal elimination half-life of approximately 5 to 7 days. The estimated half-life of N-desmethyl tamoxifen is 14 days.

Clearance

Clearance (CL/F) as body weight adjusted in female pediatric patients was approximately 2.3-fold higher than in female breast cancer patients.

Toxicity

Signs observed at the highest doses following studies to determine LD50 in animals were respiratory difficulties and convulsions.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tamoxifen Action PathwayDrug action
Tamoxifen Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*4(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of tamoxifen resulting in reduced plasma concentrations its active form endoxifen.Details
Coagulation factor V---(A;A) / (A;G)A alleleADR Directly StudiedPatients with this genotype have increased risk of a thromboembolic event with tamoxifen.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor response to drug treatment, shorter time to relapseDetails

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Abiraterone resulting in a loss in efficacy.Approved
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Tamoxifen.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Tamoxifen.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Tamoxifen.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Tamoxifen.Experimental
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Tamoxifen.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Tamoxifen.Approved
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Tamoxifen.Approved, Investigational
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Tamoxifen.Approved, Withdrawn
AmiodaroneThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Amiodarone resulting in a loss in efficacy.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Tamoxifen.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Tamoxifen.Approved, Investigational
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Tamoxifen.Approved
AnagrelideTamoxifen may increase the QTc-prolonging activities of Anagrelide.Approved
AnastrozoleThe serum concentration of Anastrozole can be decreased when it is combined with Tamoxifen.Approved, Investigational
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Tamoxifen.Approved
ApixabanThe metabolism of Apixaban can be decreased when combined with Tamoxifen.Approved
AprepitantThe serum concentration of Tamoxifen can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Tamoxifen.Approved, Investigational
ArmodafinilThe metabolism of Tamoxifen can be decreased when combined with Armodafinil.Approved, Investigational
Arsenic trioxideTamoxifen may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Artemether resulting in a loss in efficacy.Approved
AsenapineTamoxifen may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirThe metabolism of Tamoxifen can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Atomoxetine resulting in a loss in efficacy.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Tamoxifen is combined with Atorvastatin.Approved
AzelastineThe metabolism of Azelastine can be decreased when combined with Tamoxifen.Approved
AzithromycinTamoxifen may increase the QTc-prolonging activities of Azithromycin.Approved
BedaquilineTamoxifen may increase the QTc-prolonging activities of Bedaquiline.Approved
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Tamoxifen.Approved
BeraprostThe metabolism of Beraprost can be decreased when combined with Tamoxifen.Investigational
BetaxololThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Betaxolol resulting in a loss in efficacy.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Tamoxifen.Approved, Investigational
BexaroteneThe serum concentration of Tamoxifen can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Tamoxifen can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Tamoxifen can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Tamoxifen can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Tamoxifen.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Tamoxifen.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Tamoxifen.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Tamoxifen.Approved
BuprenorphineThe metabolism of Buprenorphine can be decreased when combined with Tamoxifen.Approved, Illicit, Investigational, Vet Approved
BupropionThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Bupropion resulting in a loss in efficacy.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Tamoxifen.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Tamoxifen.Approved
CaffeineThe metabolism of Tamoxifen can be decreased when combined with Caffeine.Approved
CapecitabineThe metabolism of Tamoxifen can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Tamoxifen can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Tamoxifen.Approved
CelecoxibThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Celecoxib resulting in a loss in efficacy.Approved, Investigational
CeritinibThe serum concentration of Tamoxifen can be increased when it is combined with Ceritinib.Approved
CerivastatinThe metabolism of Cerivastatin can be decreased when combined with Tamoxifen.Withdrawn
ChloramphenicolThe metabolism of Tamoxifen can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Chloroquine resulting in a loss in efficacy.Approved, Vet Approved
ChlorpromazineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Chlorpromazine resulting in a loss in efficacy.Approved, Vet Approved
CholecalciferolThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Cholecalciferol resulting in a loss in efficacy.Approved, Nutraceutical
Cholic AcidTamoxifen may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
CimetidineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Cimetidine resulting in a loss in efficacy.Approved
CinacalcetThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Cinacalcet resulting in a loss in efficacy.Approved
CiprofloxacinTamoxifen may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideTamoxifen may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Citalopram resulting in a loss in efficacy.Approved
ClarithromycinThe metabolism of Tamoxifen can be decreased when combined with Clarithromycin.Approved
ClemastineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Clemastine resulting in a loss in efficacy.Approved
ClobazamThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Clobazam resulting in a loss in efficacy.Approved, Illicit
ClomipramineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Clomipramine resulting in a loss in efficacy.Approved, Vet Approved
ClopidogrelThe metabolism of Tamoxifen can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Tamoxifen.Experimental
ClotrimazoleThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Clotrimazole resulting in a loss in efficacy.Approved, Vet Approved
ClozapineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Clozapine resulting in a loss in efficacy.Approved
CobicistatThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Cobicistat resulting in a loss in efficacy.Approved
CocaineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Cocaine resulting in a loss in efficacy.Approved, Illicit
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Tamoxifen.Approved
ConivaptanThe serum concentration of Tamoxifen can be increased when it is combined with Conivaptan.Approved, Investigational
CrisaboroleThe metabolism of Tamoxifen can be decreased when combined with Crisaborole.Approved
CrizotinibTamoxifen may increase the QTc-prolonging activities of Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Tamoxifen.Approved, Investigational
CyclosporineThe metabolism of Tamoxifen can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Tamoxifen.Experimental
Cyproterone acetateThe serum concentration of Tamoxifen can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Tamoxifen.Approved
DabrafenibThe serum concentration of Tamoxifen can be decreased when it is combined with Dabrafenib.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Tamoxifen.Approved, Investigational
DarifenacinThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Darifenacin resulting in a loss in efficacy.Approved, Investigational
DarunavirThe serum concentration of Tamoxifen can be increased when it is combined with Darunavir.Approved
DasabuvirThe metabolism of Dasabuvir can be decreased when combined with Tamoxifen.Approved
DasatinibThe serum concentration of Tamoxifen can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Tamoxifen can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Delavirdine resulting in a loss in efficacy.Approved
DesipramineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Desipramine resulting in a loss in efficacy.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Tamoxifen.Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Tamoxifen.Approved
DiazepamThe metabolism of Diazepam can be decreased when combined with Tamoxifen.Approved, Illicit, Vet Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Tamoxifen.Approved, Vet Approved
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Tamoxifen.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Tamoxifen.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Tamoxifen.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Tamoxifen.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Tamoxifen.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Tamoxifen.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Tamoxifen.Experimental
DihydroergotamineThe metabolism of Tamoxifen can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Tamoxifen can be decreased when combined with Diltiazem.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Tamoxifen.Experimental
DiphenhydramineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Diphenhydramine resulting in a loss in efficacy.Approved
DisopyramideTamoxifen may increase the QTc-prolonging activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Tamoxifen.Approved, Investigational
DofetilideTamoxifen may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronTamoxifen may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneTamoxifen may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DosulepinThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Dosulepin resulting in a loss in efficacy.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Tamoxifen.Approved, Investigational
DoxorubicinThe metabolism of Tamoxifen can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Tamoxifen can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Dronedarone resulting in a loss in efficacy.Approved
DroperidolTamoxifen may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DuloxetineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Duloxetine resulting in a loss in efficacy.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Tamoxifen.Approved
EfavirenzThe metabolism of Tamoxifen can be decreased when combined with Efavirenz.Approved, Investigational
EliglustatThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Eliglustat resulting in a loss in efficacy.Approved
EltrombopagThe serum concentration of Tamoxifen can be increased when it is combined with Eltrombopag.Approved
EnasidenibThe metabolism of Enasidenib can be decreased when combined with Tamoxifen.Approved
EnzalutamideThe serum concentration of Tamoxifen can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Tamoxifen.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Tamoxifen.Approved
ErlotinibThe metabolism of Erlotinib can be decreased when combined with Tamoxifen.Approved, Investigational
ErythromycinTamoxifen may increase the QTc-prolonging activities of Erythromycin.Approved, Vet Approved
EscitalopramTamoxifen may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Tamoxifen can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Tamoxifen can be decreased when combined with Esomeprazole.Approved, Investigational
EstradiolThe metabolism of Estradiol can be decreased when combined with Tamoxifen.Approved, Investigational, Vet Approved
EszopicloneThe metabolism of Eszopiclone can be decreased when combined with Tamoxifen.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Tamoxifen.Withdrawn
EtravirineThe metabolism of Tamoxifen can be decreased when combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Tamoxifen.Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Tamoxifen.Approved
FlecainideTamoxifen may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FloxuridineThe metabolism of Tamoxifen can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Tamoxifen can be decreased when combined with Fluconazole.Approved
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Tamoxifen.Investigational
FluorouracilThe metabolism of Tamoxifen can be decreased when combined with Fluorouracil.Approved
FluoxetineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Fluoxetine resulting in a loss in efficacy.Approved, Vet Approved
FlupentixolTamoxifen may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluvastatinThe metabolism of Tamoxifen can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Fluvoxamine resulting in a loss in efficacy.Approved, Investigational
FosamprenavirThe metabolism of Tamoxifen can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Tamoxifen can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Tamoxifen can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Tamoxifen can be increased when it is combined with Fusidic Acid.Approved
Gadobenic acidTamoxifen may increase the QTc-prolonging activities of Gadobenic acid.Approved
GemfibrozilThe metabolism of Tamoxifen can be decreased when combined with Gemfibrozil.Approved
GemifloxacinTamoxifen may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Tamoxifen.Experimental
GoserelinTamoxifen may increase the QTc-prolonging activities of Goserelin.Approved
GranisetronTamoxifen may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
HalofantrineThe metabolism of Halofantrine can be decreased when combined with Tamoxifen.Approved
HaloperidolThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Haloperidol resulting in a loss in efficacy.Approved
IbuprofenThe metabolism of Ibuprofen can be decreased when combined with Tamoxifen.Approved
IbutilideTamoxifen may increase the QTc-prolonging activities of Ibutilide.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Tamoxifen.Approved
IloperidoneTamoxifen may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe metabolism of Tamoxifen can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Imipramine resulting in a loss in efficacy.Approved
IndinavirThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Indinavir resulting in a loss in efficacy.Approved
IrbesartanThe metabolism of Tamoxifen can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Tamoxifen can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Isoniazid resulting in a loss in efficacy.Approved
IsradipineThe metabolism of Tamoxifen can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Tamoxifen can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Tamoxifen can be increased when it is combined with Ivacaftor.Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Tamoxifen.Approved
KetamineThe metabolism of Ketamine can be decreased when combined with Tamoxifen.Approved, Vet Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Tamoxifen.Approved, Investigational
KetoconazoleThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ketoconazole resulting in a loss in efficacy.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Tamoxifen.Experimental
LansoprazoleThe metabolism of Lansoprazole can be decreased when combined with Tamoxifen.Approved, Investigational
LapatinibThe metabolism of Lapatinib can be decreased when combined with Tamoxifen.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Tamoxifen.Approved
LeflunomideThe metabolism of Tamoxifen can be decreased when combined with Leflunomide.Approved, Investigational
LenvatinibTamoxifen may increase the QTc-prolonging activities of Lenvatinib.Approved
LetrozoleThe serum concentration of Letrozole can be decreased when it is combined with Tamoxifen.Approved, Investigational
LeuprolideTamoxifen may increase the QTc-prolonging activities of Leuprolide.Approved, Investigational
LevofloxacinTamoxifen may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LevomilnacipranThe metabolism of Levomilnacipran can be decreased when combined with Tamoxifen.Approved
LicofeloneThe metabolism of Licofelone can be decreased when combined with Tamoxifen.Investigational
LidocaineThe metabolism of Tamoxifen can be decreased when combined with Lidocaine.Approved, Vet Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Tamoxifen.Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Tamoxifen.Approved, Investigational
LobeglitazoneThe metabolism of Tamoxifen can be decreased when combined with Lobeglitazone.Approved, Investigational
LoperamideThe metabolism of Loperamide can be decreased when combined with Tamoxifen.Approved
LopinavirThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Lopinavir resulting in a loss in efficacy.Approved
LoratadineThe metabolism of Loratadine can be decreased when combined with Tamoxifen.Approved
LorcaserinThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Lorcaserin resulting in a loss in efficacy.Approved
LosartanThe metabolism of Tamoxifen can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Tamoxifen can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Tamoxifen can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Tamoxifen can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Lumefantrine resulting in a loss in efficacy.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Tamoxifen.Illicit, Investigational, Withdrawn
ManidipineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Manidipine resulting in a loss in efficacy.Approved, Investigational
Mefenamic acidThe metabolism of Mefenamic acid can be decreased when combined with Tamoxifen.Approved
MeloxicamThe metabolism of Meloxicam can be decreased when combined with Tamoxifen.Approved, Vet Approved
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Tamoxifen.Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Tamoxifen.Experimental
MethadoneThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Methadone resulting in a loss in efficacy.Approved
MethotrimeprazineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Methotrimeprazine resulting in a loss in efficacy.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Tamoxifen.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Tamoxifen.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Tamoxifen.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Tamoxifen.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Tamoxifen.Experimental
MexiletineThe metabolism of Tamoxifen can be decreased when combined with Mexiletine.Approved
MidostaurinThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Midostaurin resulting in a loss in efficacy.Approved
MifepristoneThe serum concentration of Tamoxifen can be increased when it is combined with Mifepristone.Approved, Investigational
MipomersenTamoxifen may increase the hepatotoxic activities of Mipomersen.Approved
MirabegronThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Mirabegron resulting in a loss in efficacy.Approved
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Tamoxifen.Approved
MitotaneThe serum concentration of Tamoxifen can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Tamoxifen can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Tamoxifen can be decreased when combined with Modafinil.Approved, Investigational
MorphineThe metabolism of Morphine can be decreased when combined with Tamoxifen.Approved, Investigational
MoxifloxacinTamoxifen may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
muraglitazarThe metabolism of muraglitazar can be decreased when combined with Tamoxifen.Investigational
Mycophenolate mofetilThe metabolism of Mycophenolate mofetil can be decreased when combined with Tamoxifen.Approved, Investigational
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Tamoxifen.Approved
NaloxoneThe metabolism of Naloxone can be decreased when combined with Tamoxifen.Approved, Vet Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Tamoxifen.Approved, Vet Approved
NefazodoneThe metabolism of Tamoxifen can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Tamoxifen can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Tamoxifen can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Nevirapine resulting in a loss in efficacy.Approved
NicardipineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Nicardipine resulting in a loss in efficacy.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Tamoxifen.Approved, Investigational
NicotineThe metabolism of Nicotine can be decreased when combined with Tamoxifen.Approved
NilotinibThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Nilotinib resulting in a loss in efficacy.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Tamoxifen.Approved
OdanacatibThe metabolism of Odanacatib can be decreased when combined with Tamoxifen.Investigational
OfloxacinTamoxifen may increase the QTc-prolonging activities of Ofloxacin.Approved
OlaparibThe metabolism of Tamoxifen can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Tamoxifen.Experimental, Investigational
OlodaterolThe metabolism of Olodaterol can be decreased when combined with Tamoxifen.Approved
OmbitasvirThe metabolism of Ombitasvir can be decreased when combined with Tamoxifen.Approved
OmeprazoleThe metabolism of Tamoxifen can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronTamoxifen may increase the QTc-prolonging activities of Ondansetron.Approved
OsimertinibThe serum concentration of Tamoxifen can be increased when it is combined with Osimertinib.Approved
OspemifeneThe risk or severity of adverse effects can be increased when Tamoxifen is combined with Ospemifene.Approved
OuabainOuabain may decrease the cardiotoxic activities of Tamoxifen.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Tamoxifen.Approved, Vet Approved
PalbociclibThe serum concentration of Tamoxifen can be increased when it is combined with Palbociclib.Approved
PaliperidoneTamoxifen may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Panobinostat resulting in a loss in efficacy.Approved, Investigational
PantoprazoleThe metabolism of Tamoxifen can be decreased when combined with Pantoprazole.Approved
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Tamoxifen.Approved
ParoxetineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Paroxetine resulting in a loss in efficacy.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Tamoxifen.Approved
Peginterferon alfa-2bThe serum concentration of Tamoxifen can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentamidineTamoxifen may increase the QTc-prolonging activities of Pentamidine.Approved
PentobarbitalThe metabolism of Tamoxifen can be increased when combined with Pentobarbital.Approved, Vet Approved
PerflutrenTamoxifen may increase the QTc-prolonging activities of Perflutren.Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Tamoxifen.Approved, Investigational, Vet Approved, Withdrawn
PerospironeThe metabolism of Perospirone can be decreased when combined with Tamoxifen.Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Tamoxifen.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Tamoxifen.Experimental
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Tamoxifen.Approved, Investigational
PhenobarbitalThe metabolism of Tamoxifen can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Tamoxifen.Approved, Investigational
PhenytoinThe metabolism of Tamoxifen can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideTamoxifen may increase the QTc-prolonging activities of Pimozide.Approved
PioglitazoneThe metabolism of Pioglitazone can be decreased when combined with Tamoxifen.Approved, Investigational
PiroxicamThe metabolism of Piroxicam can be decreased when combined with Tamoxifen.Approved, Investigational
PitavastatinThe metabolism of Pitavastatin can be decreased when combined with Tamoxifen.Approved
PonatinibThe metabolism of Ponatinib can be decreased when combined with Tamoxifen.Approved
PosaconazoleThe metabolism of Tamoxifen can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Tamoxifen.Approved
PrimaquineTamoxifen may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe metabolism of Tamoxifen can be increased when combined with Primidone.Approved, Vet Approved
ProcainamideTamoxifen may increase the QTc-prolonging activities of Procainamide.Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Tamoxifen.Approved, Vet Approved
PromazineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Promazine resulting in a loss in efficacy.Approved, Vet Approved
PropafenoneTamoxifen may increase the QTc-prolonging activities of Propafenone.Approved
PropofolThe metabolism of Propofol can be decreased when combined with Tamoxifen.Approved, Investigational, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Tamoxifen.Experimental
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Tamoxifen.Approved
PyrimethamineThe metabolism of Tamoxifen can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe serum concentration of Tamoxifen can be increased when it is combined with Quazepam.Approved, Illicit
QuetiapineTamoxifen may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Quinidine resulting in a loss in efficacy.Approved
QuinineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Quinine resulting in a loss in efficacy.Approved
RanolazineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ranolazine resulting in a loss in efficacy.Approved, Investigational
RepaglinideThe metabolism of Repaglinide can be decreased when combined with Tamoxifen.Approved, Investigational
RifabutinThe metabolism of Tamoxifen can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Tamoxifen can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Tamoxifen can be increased when combined with Rifapentine.Approved
RifaximinThe metabolism of Tamoxifen can be increased when combined with Rifaximin.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Tamoxifen.Approved
RiociguatThe metabolism of Riociguat can be decreased when combined with Tamoxifen.Approved
RitonavirThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ritonavir resulting in a loss in efficacy.Approved, Investigational
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Tamoxifen.Investigational, Withdrawn
RolapitantThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Rolapitant resulting in a loss in efficacy.Approved
RopiniroleThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ropinirole resulting in a loss in efficacy.Approved, Investigational
RosiglitazoneThe metabolism of Rosiglitazone can be decreased when combined with Tamoxifen.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Tamoxifen.Approved
SaquinavirThe metabolism of Tamoxifen can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Tamoxifen.Approved
SecobarbitalThe metabolism of Tamoxifen can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Tamoxifen.Approved, Investigational, Vet Approved
SelexipagThe metabolism of Selexipag can be decreased when combined with Tamoxifen.Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Tamoxifen.Approved
SertralineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Sertraline resulting in a loss in efficacy.Approved
SildenafilThe metabolism of Tamoxifen can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Tamoxifen.Approved
SiltuximabThe serum concentration of Tamoxifen can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Tamoxifen can be increased when it is combined with Simeprevir.Approved
SimvastatinThe metabolism of Simvastatin can be decreased when combined with Tamoxifen.Approved
SitagliptinThe metabolism of Sitagliptin can be decreased when combined with Tamoxifen.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Tamoxifen.Approved
SorafenibThe metabolism of Tamoxifen can be decreased when combined with Sorafenib.Approved, Investigational
SotalolTamoxifen may increase the QTc-prolonging activities of Sotalol.Approved
St. John's WortThe serum concentration of Tamoxifen can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Tamoxifen can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Tamoxifen can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Tamoxifen can be decreased when combined with Sulfamethoxazole.Approved
SulfinpyrazoneThe metabolism of Sulfinpyrazone can be decreased when combined with Tamoxifen.Approved
SulfisoxazoleThe metabolism of Tamoxifen can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TazaroteneThe metabolism of Tazarotene can be decreased when combined with Tamoxifen.Approved, Investigational
TelaprevirThe metabolism of Tamoxifen can be decreased when combined with Telaprevir.Approved, Withdrawn
TelavancinTamoxifen may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinThe metabolism of Tamoxifen can be decreased when combined with Telithromycin.Approved
TemazepamThe metabolism of Temazepam can be decreased when combined with Tamoxifen.Approved
Tenofovir disoproxilThe metabolism of Tamoxifen can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TerbinafineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Terbinafine resulting in a loss in efficacy.Approved, Investigational, Vet Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Tamoxifen.Experimental
TeriflunomideThe serum concentration of Tamoxifen can be decreased when it is combined with Teriflunomide.Approved
TestosteroneThe metabolism of Testosterone can be decreased when combined with Tamoxifen.Approved, Investigational
TetrabenazineTamoxifen may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe metabolism of Tamoxifen can be decreased when combined with Theophylline.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Tamoxifen.Approved, Withdrawn
ThiotepaThe metabolism of Tamoxifen can be decreased when combined with Thiotepa.Approved
TicagrelorThe metabolism of Tamoxifen can be decreased when combined with Ticagrelor.Approved
TiclopidineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ticlopidine resulting in a loss in efficacy.Approved
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Tamoxifen.Experimental
TipranavirThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Tipranavir resulting in a loss in efficacy.Approved, Investigational
TocilizumabThe serum concentration of Tamoxifen can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Tamoxifen can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Tamoxifen can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Tamoxifen can be decreased when combined with Topiroxostat.Approved, Investigational
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Tamoxifen.Approved, Investigational
TorasemideThe metabolism of Torasemide can be decreased when combined with Tamoxifen.Approved
ToremifeneTamoxifen may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TranylcypromineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Tranylcypromine resulting in a loss in efficacy.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Tamoxifen.Approved, Investigational
TretinoinThe metabolism of Tretinoin can be decreased when combined with Tamoxifen.Approved, Investigational, Nutraceutical
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Tamoxifen.Approved
TrimethoprimThe metabolism of Tamoxifen can be decreased when combined with Trimethoprim.Approved, Vet Approved
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Tamoxifen.Investigational, Withdrawn
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Tamoxifen.Approved, Investigational, Nutraceutical
Valproic AcidThe metabolism of Tamoxifen can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Tamoxifen can be decreased when combined with Valsartan.Approved, Investigational
VandetanibTamoxifen may increase the QTc-prolonging activities of Vandetanib.Approved
VelpatasvirThe metabolism of Velpatasvir can be decreased when combined with Tamoxifen.Approved
VenlafaxineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Venlafaxine resulting in a loss in efficacy.Approved
VerapamilThe metabolism of Tamoxifen can be decreased when combined with Verapamil.Approved
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Tamoxifen.Approved, Investigational
VoriconazoleThe metabolism of Tamoxifen can be decreased when combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Tamoxifen.Approved
VoxilaprevirThe metabolism of Voxilaprevir can be decreased when combined with Tamoxifen.Approved
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Tamoxifen.Approved
ZafirlukastThe metabolism of Tamoxifen can be decreased when combined with Zafirlukast.Approved, Investigational
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Tamoxifen.Approved
ZiprasidoneThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Ziprasidone resulting in a loss in efficacy.Approved
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Tamoxifen.Approved
ZucapsaicinThe metabolism of Tamoxifen can be decreased when combined with Zucapsaicin.Approved
ZuclopenthixolTamoxifen may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Chengjian Mao, "Tamoxifen and 4-hydroxytamoxifen-activated system for regulated production of proteins in eukaryotic cells." U.S. Patent US20030199022, issued October 23, 2003.

US20030199022
General References
  1. Jordan VC: Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer. Br J Pharmacol. 2006 Jan;147 Suppl 1:S269-76. [PubMed:16402113]
  2. Jordan VC: Fourteenth Gaddum Memorial Lecture. A current view of tamoxifen for the treatment and prevention of breast cancer. Br J Pharmacol. 1993 Oct;110(2):507-17. [PubMed:8242225]
  3. Howell A, Cuzick J, Baum M, Buzdar A, Dowsett M, Forbes JF, Hoctin-Boes G, Houghton J, Locker GY, Tobias JS: Results of the ATAC (Arimidex, Tamoxifen, Alone or in Combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet. 2005 Jan 1-7;365(9453):60-2. [PubMed:15639680]
  4. Steiner AZ, Terplan M, Paulson RJ: Comparison of tamoxifen and clomiphene citrate for ovulation induction: a meta-analysis. Hum Reprod. 2005 Jun;20(6):1511-5. Epub 2005 Apr 21. [PubMed:15845599]
  5. van Bommel EF, Hendriksz TR, Huiskes AW, Zeegers AG: Brief communication: tamoxifen therapy for nonmalignant retroperitoneal fibrosis. Ann Intern Med. 2006 Jan 17;144(2):101-6. [PubMed:16418409]
External Links
Human Metabolome Database
HMDB14813
KEGG Drug
D00966
KEGG Compound
C07108
PubChem Compound
2733526
PubChem Substance
46505515
ChemSpider
2015313
BindingDB
20607
ChEBI
41774
ChEMBL
CHEMBL83
Therapeutic Targets Database
DAP000108
PharmGKB
PA451581
IUPHAR
1016
Guide to Pharmacology
GtP Drug Page
HET
CTX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tamoxifen
ATC Codes
L02BA01 — Tamoxifen
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
1ya4
FDA label
Download (102 KB)
MSDS
Download (74.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedPreventionBarrett's Metaplasia1
1Active Not RecruitingBasic ScienceTumors, Solid1
1Active Not RecruitingTreatmentBreast Cancer - Female / Breast Cancer - Male / Cancer, Breast1
1Active Not RecruitingTreatmentHormone Receptor Positive, HER2-negative, Advanced Breast Cancer1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentCancer, Breast4
1CompletedTreatmentCancer, Ovarian1
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentNeoplasms Metastasis / Sarcoma, Osteogenic1
1Not Yet RecruitingBasic ScienceCancers / Neoplasms, Gastrointestinal1
1Not Yet RecruitingTreatmentDuchenne's Muscular Dystrophy (DMD)1
1RecruitingOtherCancer, Breast1
1RecruitingTreatmentCancer of the Uterus / Cancer, Breast / Cancer, Ovarian1
1RecruitingTreatmentCancer, Breast / Carcinoma, Breast / Malignant Neoplasm of Breast1
1RecruitingTreatmentNeoplasms, Breast1
1Unknown StatusTreatmentCancer, Breast1
1, 2RecruitingTreatmentNeoplasms, Breast1
1, 2TerminatedTreatmentCancer, Breast / Neoplasms, Breast / Tumors, Breast1
1, 2Unknown StatusTreatmentALS Functional Ration Scale / Amyotrophic Lateral Sclerosis (ALS) / MTOR / Tamoxifen / TAR-DNA-binding Protein-431
2Active Not RecruitingPreventionCancer, Breast1
2Active Not RecruitingTreatmentAdvanced, Persistent, or Recurrent Endometrial Cancer1
2Active Not RecruitingTreatmentCancer, Breast6
2Active Not RecruitingTreatmentDesmoid Tumors1
2Active Not RecruitingTreatmentErectile Dysfunction (ED) / Lower Urinary Tract Symptoms (LUTS) / Prostate Cancer1
2Active Not RecruitingTreatmentEstrogen Receptor Positive / HER2/Neu Negative / Recurrent Breast Carcinoma / Stage III Breast Cancer / Stage III Breast Cancer AJCC V7 / Stage IIIA Breast Cancer / Stage IIIA Breast Cancer AJCC v7 / Stage IIIB Breast Cancer / Stage IIIB Breast Cancer AJCC v7 / Stage IIIC Breast Cancer / Stage IIIC Breast Cancer AJCC v7 / Stage IV Breast Cancer / Stage IV Breast Cancer AJCC v6 and v71
2Active Not RecruitingTreatmentEstrogen Receptor-Positive Breast Cancer / HER2-Negative Breast Cancer / Progesterone Receptor-positive Breast Cancer / Recurrent Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
2Active Not RecruitingTreatmentMTor Protein / Neoplasms, Breast1
2CompletedNot AvailableAmyotrophic Lateral Sclerosis (ALS)1
2CompletedPreventionCancer, Breast2
2CompletedPreventionCancer, Breast / Hereditary Breast/Ovarian Cancer (brca1, brca2)1
2CompletedSupportive CareCancer, Breast / Menopausal Hot Flushes1
2CompletedTreatmentAdrenocortical Carcinoma / Brain and Central Nervous System Tumors / Head and Neck Carcinoma / Liver Cancer / Mesothelioma, Malignant / Pheochromocytomas / Sarcomas1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2CompletedTreatmentBiochemical-recurrent Only Epithelial Ovarian Cancer / Fallopian Tube Cancer / Primary Peritoneal Carcinoma1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentBipolar Disorder (BD) / Mania / Schizoaffective Disorders1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentBrain and Central Nervous System Tumors / Metastatic Cancers / Unspecified Adult Solid Tumor, Protocol Specific1
2CompletedTreatmentCancer of the Fallopian Tube / Cancer, Ovarian / Malignant Peritoneal Neoplasm1
2CompletedTreatmentCancer, Breast12
2CompletedTreatmentCancer, Breast / Neoplasms, Breast2
2CompletedTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor-Positive Breast Cancer1
2CompletedTreatmentEndometrial Carcinoma / Recurrent Uterine Corpus Carcinoma / Stage IIIA Uterine Corpus Cancer / Stage IIIB Uterine Corpus Cancer / Stage IIIC1 Uterine Corpus Cancer / Stage IIIC2 Uterine Corpus Cancer / Stage IVA Uterine Corpus Cancer / Stage IVB Uterine Corpus Cancer1
2CompletedTreatmentEstrogen Receptor Positive / Male Breast Carcinoma / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentEstrogen Receptor-negative Breast Cancer / Estrogen Receptor-Positive Breast Cancer / Her2-Positive Breast Cancer / Progesterone Receptor-negative Breast Cancer / Progesterone Receptor-positive Breast Cancer / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer1
2CompletedTreatmentEstrogen Receptor-negative Breast Cancer / Estrogen Receptor-Positive Breast Cancer / Inflammatory carcinoma of the breast / Male Breast Cancer / Progesterone Receptor-negative Breast Cancer / Progesterone Receptor-positive Breast Cancer / Stage IIIB Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentGliomas1
2CompletedTreatmentGynaecomastia / Prostate Cancer1
2CompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT)1
2CompletedTreatmentMale Breast Cancer / Stage II Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer1
2CompletedTreatmentMetastatic Breast Cancer (MBC)2
2CompletedTreatmentNeoplasms, Breast3
2CompletedTreatmentNewly Diagnosed Hormone Positive Clinical Stage 1 or 2 Breast Cancer1
2CompletedTreatmentUrinary Bladder Neoplasms1
2Enrolling by InvitationPreventionMammographic Density Reduction / Risk Reduction1
2Not Yet RecruitingOtherCancer, Breast1
2Not Yet RecruitingTreatmentBreast Cancer Stage II / Breast Cancer Stage III / Cancer, Breast1
2Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Meningitis / Meningitis streptococcal / Meningoencephalitis1
2Not Yet RecruitingTreatmentNeoplasms, Breast1
2RecruitingBasic ScienceCancer, Breast2
2RecruitingScreeningNon Metastatic Breast Cancer1
2RecruitingTreatmentBladder Cancers2
2RecruitingTreatmentBreakthrough Bleeding / Haemorrhage / Implants1
2RecruitingTreatmentCancer of Breast / Cancer of the Breast / Cancer, Breast / Neoplasms, Breast1
2RecruitingTreatmentCancer, Breast3
2RecruitingTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor Positive1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Estrogen Receptor Positive Tumor1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Hormone Receptor Positive Tumor1
2RecruitingTreatmentEstrogen Receptor Positive Breast Cancer1
2RecruitingTreatmentEstrogen Receptor Positive Breast Cancer / Hormone Receptor Positive Malignant Neoplasm of Breast / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Metastatic Breast Cancer (MBC) / Progesterone Receptor Positive Tumor1
2RecruitingTreatmentMetastatic Breast Cancer (MBC)2
2RecruitingTreatmentNeoplasms, Breast3
2RecruitingTreatmentOvarian Carcinoma1
2RecruitingTreatmentUterine Cervical Neoplasms1
2TerminatedBasic ScienceBreast Cancer Invasive Nos / Stage I Breast Carcinoma / Stage II Breast Cancer / Stage III Breast Cancer1
2TerminatedTreatmentCancer, Breast2
2TerminatedTreatmentCancer, Breast / Metastatic Disease1
2TerminatedTreatmentCarcinoma, Breast1
2TerminatedTreatmentMetastatic Breast Cancer (MBC) / One to five years postmenopausal1
2TerminatedTreatmentNeoplasms, Breast1
2Unknown StatusDiagnosticCancer, Ovarian / Fallopian Tube Cancer / Primary Peritoneal Cavity Cancer1
2Unknown StatusPreventionCancer, Breast1
2Unknown StatusTreatmentBrain and Central Nervous System Tumors2
2Unknown StatusTreatmentCancer, Breast3
2Unknown StatusTreatmentIntraocular Melanoma1
2Unknown StatusTreatmentMelanoma (Skin)1
2Unknown StatusTreatmentRetroperitoneal Fibrosis1
2, 3Not Yet RecruitingPreventionDiscomfort / Pain1
2, 3RecruitingTreatmentLow Grade Ovarian Serous Adenocarcinoma / Micropapillary Serous Carcinoma / Ovarian Serous Adenocarcinoma / Primary Peritoneal Serous Adenocarcinoma / Recurrent Ovarian Carcinoma / Recurrent Primary Peritoneal Carcinoma1
2, 3TerminatedTreatmentCancer, Breast1
3Active Not RecruitingPreventionCancer, Breast1
3Active Not RecruitingPreventionIntraepithelial Carcinoma1
3Active Not RecruitingTreatmentAdvanced, Metastatic Breast Cancer1
3Active Not RecruitingTreatmentBreast Adenocarcinoma / Estrogen Receptor and/or Progesterone Receptor Positive / HER2/Neu Negative / Stage IA Breast Cancer / Stage IA Breast Cancer AJCC v7 / Stage IB Breast Cancer / Stage IB Breast Cancer AJCC v7 / Stage IIA Breast Cancer / Stage IIA Breast Cancer AJCC v6 and v7 / Stage IIB Breast Cancer / Stage IIB Breast Cancer AJCC v6 and v7 / Stage IIIB Breast Cancer / Stage IIIB Breast Cancer AJCC v71
3Active Not RecruitingTreatmentBreast Adenocarcinoma / HER2 Positive Breast Carcinoma / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIA Breast Cancer1
3Active Not RecruitingTreatmentCancer, Breast7
3Active Not RecruitingTreatmentCancer, Breast / Estrogen Receptor Positive Breast Cancer / Progesterone Receptor Positive Tumor / Recurrent Breast Carcinoma / Stage IA Breast Cancer / Stage IB Breast Cancer / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIA Breast Cancer1
3Active Not RecruitingTreatmentEstrogen Receptor Positive / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IV Breast Cancer1
3CompletedNot AvailableBone Density1
3CompletedNot AvailableCancer, Breast1
3CompletedNot AvailableCancer, Breast / Sleep disorders and disturbances / Tiredness1
3CompletedNot AvailableQuality of Life1
3CompletedPreventionAging / Cognition1
3CompletedPreventionCancer, Breast2
3CompletedPreventionCancer, Breast / Endometrial Cancers1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Ischemia1
3CompletedPreventionProstate Cancer1
3CompletedTreatmentBipolar Disorder (BD)1
3CompletedTreatmentCancer of the Fallopian Tube / Cancer, Ovarian / Malignant Peritoneal Neoplasm1
3CompletedTreatmentCancer, Breast33
3CompletedTreatmentCancer, Breast / Cyclophosphamide / Doxorubicin / High Risk / Positive Nodes1
3CompletedTreatmentCancer, Breast / Metastasis1
3CompletedTreatmentEarly-Stage Breast Cancer2
3CompletedTreatmentFallopian Tube Cancer / Primary Peritoneal Cavity Cancer / Recurrent Ovarian Epithelial Cancer / Stage III Ovarian Epithelial Cancer / Stage IV Ovarian Epithelial Cancer1
3CompletedTreatmentHormone Sensitive Resected Primary Breast Cancer in Postmenopausal Women1
3CompletedTreatmentLiver Cancer1
3CompletedTreatmentNeoplasms, Breast4
3Not Yet RecruitingTreatmentDuchenne's Muscular Dystrophy (DMD)1
3RecruitingTreatmentCancer, Breast6
3RecruitingTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor and/or Progesterone Receptor Positive / HER2/Neu Negative / Invasive Breast Carcinoma / Multicentric Breast Carcinoma / Multifocal Breast Carcinoma / Synchronous Bilateral Breast Carcinoma1
3RecruitingTreatmentInfertilities1
3RecruitingTreatmentMale Breast Cancer1
3RecruitingTreatmentMalignant Neoplasm of Female Breast1
3RecruitingTreatmentMetastatic Breast Cancer (MBC)1
3TerminatedTreatmentCancer, Breast3
3TerminatedTreatmentCardiac Toxicity / Inflammatory carcinoma of the breast / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IV Breast Cancer1
3TerminatedTreatmentEndometrial Cancers1
3Unknown StatusTreatmentCancer, Breast12
3Unknown StatusTreatmentCancer, Breast / Pulmonary Fibrosis1
3WithdrawnTreatmentRecurrent Breast Cancer / Stage IV Breast Cancer1
4Active Not RecruitingTreatmentHormono-depending Adjuvant Breast Cancer1
4CompletedNot AvailableCancer, Breast1
4CompletedBasic SciencePharmacokinetics1
4CompletedHealth Services ResearchCancer, Breast1
4CompletedSupportive CarePolycystic Ovarian Syndrome1
4CompletedTreatmentBenign Breast Disease / Fibroadenoma / Fibrocystic Disease of Breast / Mastodynia1
4CompletedTreatmentCancer, Breast1
4CompletedTreatmentMenstruation Disturbances1
4Not Yet RecruitingTreatmentEndometrium1
4Not Yet RecruitingTreatmentHER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage 0 Breast Cancer / Stage IA Breast Cancer1
4Not Yet RecruitingTreatmentInfertilities1
4RecruitingPreventionHypermenorrhea / Medicated Intrauterine Devices / Metrorrhagia1
4RecruitingTreatmentCYP2D6 Polymorphism1
4RecruitingTreatmentCancer, Breast2
4RecruitingTreatmentSexuality1
4Unknown StatusTreatmentCancer, Breast1
Not AvailableActive Not RecruitingNot AvailableCancer, Breast / Depression / Menopausal Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
Not AvailableActive Not RecruitingHealth Services ResearchCancer, Breast1
Not AvailableCompletedNot AvailableAntineoplastic Agents / Neoplasms, Breast / Survival Analysis / Therapeutic Uses1
Not AvailableCompletedNot AvailableArthralgia / BMI >30 kg/m2 / Cancer, Breast1
Not AvailableCompletedNot AvailableCancer, Breast1
Not AvailableCompletedDiagnosticCancer, Breast / CYP2D6 Polymorphism1
Not AvailableCompletedPreventionCancer, Breast / Hodgkins Disease (HD)1
Not AvailableCompletedTreatmentCancer, Breast2
Not AvailableCompletedTreatmentDuctal Breast Carcinoma In Situ / Lobular Breast Carcinoma In Situ / Stage II Breast Cancer / Stage IIA Breast Cancer / Stage IIB Breast Cancer / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer1
Not AvailableCompletedTreatmentEndometrium / Estrogens / Lipemia / Mammography / Ultrasonography1
Not AvailableNot Yet RecruitingNot AvailableCancer, Breast1
Not AvailableNot Yet RecruitingBasic ScienceHigh Background Uptake on MBI1
Not AvailableRecruitingTreatmentBreast Cancer Nos Premenopausal1
Not AvailableRecruitingTreatmentCancer, Breast1
Not AvailableTerminatedNot AvailableCancer, Breast2
Not AvailableUnknown StatusNot AvailableCYP2D6 / Genotyping / Neoplasms, Breast / Tamoxifen1
Not AvailableUnknown StatusTreatmentCancer, Breast1
Not AvailableUnknown StatusTreatmentCancer, Breast / Menopausal Symptoms1
Not AvailableUnknown StatusTreatmentInfertilities1

Pharmacoeconomics

Manufacturers
  • Rosemont group ltd
  • Astrazeneca pharmaceuticals lp
  • Aegis pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Pharmachemie bv
  • Roxane laboratories inc
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Watson laboratories inc florida
Packagers
Dosage forms
FormRouteStrength
TabletOral10 mg
TabletOral20 mg
LiquidOral10 mg/5mL
LiquidOral20 mg/10mL
TabletOral10 mg/1
TabletOral20 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral20 mg/1
Prices
Unit descriptionCostUnit
Tamoxifen citrate powder50.03USD g
Nolvadex 20 mg tablet4.46USD tablet
Tamoxifen Citrate 20 mg tablet3.94USD tablet
Tamoxifen 20 mg tablet3.79USD tablet
Nolvadex 10 mg tablet2.04USD tablet
Tamoxifen Citrate 10 mg tablet1.97USD tablet
Tamoxifen 10 mg tablet1.89USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6127425No1998-06-262018-06-26Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)97 °CPhysProp
water solubility0.000167 mg/mL at 25 °CMEYLAN,WM et al. (1996)
logP7.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00102 mg/mLALOGPS
logP5.93ALOGPS
logP6.35ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.43 m3·mol-1ChemAxon
Polarizability44.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.5838
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.7718
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.6225
Renal organic cation transporterInhibitor0.6715
CYP450 2C9 substrateNon-substrate0.8071
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateInhibitor0.8535
CYP450 2C9 inhibitorNon-inhibitor0.9072
CYP450 2D6 inhibitorInhibitor0.8448
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5054
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6058
BiodegradationNot ready biodegradable0.9048
Rat acute toxicity1.9882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7402
hERG inhibition (predictor II)Inhibitor0.6898
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-3972000000-38c8a6cb6c6f2505438b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-9006000000-8443975759913521d9cd

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Diphenylmethanes / Phenylpropanes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Stilbene / Diphenylmethane / Phenylpropane / Phenoxy compound / Phenol ether / Alkyl aryl ether / Benzenoid / Monocyclic benzene moiety / Tertiary aliphatic amine / Tertiary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, stilbenoid (CHEBI:41774)

Targets

Details
1. Estrogen receptor alpha
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412]
  3. Fabian CJ, Kimler BF: Chemoprevention for high-risk women: tamoxifen and beyond. Breast J. 2001 Sep-Oct;7(5):311-20. [PubMed:11906441]
  4. Cyrus K, Wehenkel M, Choi EY, Lee H, Swanson H, Kim KB: Jostling for position: optimizing linker location in the design of estrogen receptor-targeting PROTACs. ChemMedChem. 2010 Jul 5;5(7):979-85. doi: 10.1002/cmdc.201000146. [PubMed:20512796]
Details
2. Estrogen receptor beta
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Chen B, Gajdos C, Dardes R, Kidwai N, Johnston SR, Dowsett M, Jordan VC: Potential of endogenous estrogen receptor beta to influence the selective ER modulator ERbeta complex. Int J Oncol. 2005 Aug;27(2):327-35. [PubMed:16010412]
  3. Horner-Glister E, Maleki-Dizaji M, Guerin CJ, Johnson SM, Styles J, White IN: Influence of oestradiol and tamoxifen on oestrogen receptors-alpha and -beta protein degradation and non-genomic signalling pathways in uterine and breast carcinoma cells. J Mol Endocrinol. 2005 Dec;35(3):421-32. [PubMed:16326830]
  4. Girault I, Bieche I, Lidereau R: Role of estrogen receptor alpha transcriptional coregulators in tamoxifen resistance in breast cancer. Maturitas. 2006 Jul 20;54(4):342-51. Epub 2006 Jul 5. [PubMed:16822624]
  5. Mc Ilroy M, Fleming FJ, Buggy Y, Hill AD, Young LS: Tamoxifen-induced ER-alpha-SRC-3 interaction in HER2 positive human breast cancer; a possible mechanism for ER isoform specific recurrence. Endocr Relat Cancer. 2006 Dec;13(4):1135-45. [PubMed:17158759]
  6. Gruvberger-Saal SK, Bendahl PO, Saal LH, Laakso M, Hegardt C, Eden P, Peterson C, Malmstrom P, Isola J, Borg A, Ferno M: Estrogen receptor beta expression is associated with tamoxifen response in ERalpha-negative breast carcinoma. Clin Cancer Res. 2007 Apr 1;13(7):1987-94. [PubMed:17404078]
  7. Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412]
  8. Hayes DF, Skaar TC, Rae JM, Henry NL, Nguyen AT, Stearns V, Li L, Philips S, Desta Z, Flockhart DA: Estrogen receptor genotypes, menopausal status, and the effects of tamoxifen on lipid levels: revised and updated results. Clin Pharmacol Ther. 2010 Nov;88(5):626-9. doi: 10.1038/clpt.2010.143. Epub 2010 Sep 8. [PubMed:20827267]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name
EBP
Uniprot ID
Q15125
Uniprot Name
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
Molecular Weight
26352.615 Da
References
  1. Paul R, Silve S, De Nys N, Dupuy PH, Bouteiller CL, Rosenfeld J, Ferrara P, Le Fur G, Casellas P, Loison G: Both the immunosuppressant SR31747 and the antiestrogen tamoxifen bind to an emopamil-insensitive site of mammalian Delta8-Delta7 sterol isomerase. J Pharmacol Exp Ther. 1998 Jun;285(3):1296-302. [PubMed:9618436]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differenti...

Components:
References
  1. O'Brian CA, Liskamp RM, Solomon DH, Weinstein IB: Inhibition of protein kinase C by tamoxifen. Cancer Res. 1985 Jun;45(6):2462-5. [PubMed:3157445]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Yamasaki K, Sawaki M, Noda S, Muroi T, Takakura S, Mitoma H, Sakamoto S, Nakai M, Yakabe Y: Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals. Toxicology. 2004 Feb 15;195(2-3):177-86. [PubMed:14751673]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Chiu PJ, Marcoe KF, Bounds SE, Lin CH, Feng JJ, Lin A, Cheng FC, Crumb WJ, Mitchell R: Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels. J Pharmacol Sci. 2004 Jul;95(3):311-9. [PubMed:15272206]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [PubMed:16054614]
  2. Harmsen S, Meijerman I, Beijnen JH, Schellens JH: Nuclear receptor mediated induction of cytochrome P450 3A4 by anticancer drugs: a key role for the pregnane X receptor. Cancer Chemother Pharmacol. 2009 Jun;64(1):35-43. doi: 10.1007/s00280-008-0842-3. Epub 2008 Oct 7. [PubMed:18839173]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response ...
Gene Name
ESRRG
Uniprot ID
P62508
Uniprot Name
Estrogen-related receptor gamma
Molecular Weight
51305.485 Da
References
  1. Gowda K, Marks BD, Zielinski TK, Ozers MS: Development of a coactivator displacement assay for the orphan receptor estrogen-related receptor-gamma using time-resolved fluorescence resonance energy transfer. Anal Biochem. 2006 Oct 1;357(1):105-15. Epub 2006 Jul 10. [PubMed:16889744]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Higgins MJ, Stearns V: CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15. doi: 10.1007/s11912-009-0076-5. [PubMed:20425602]
  2. Kuderer NM, Peppercorn J: CYP2D6 testing in breast cancer: ready for prime time? Oncology (Williston Park). 2009 Dec;23(14):1223-32. [PubMed:20120834]
  3. Goetz MP: Tamoxifen, endoxifen, and CYP2D6: the rules for evaluating a predictive factor. Oncology (Williston Park). 2009 Dec;23(14):1233-4, 1236. [PubMed:20120835]
  4. Desta Z, Ward BA, Soukhova NV, Flockhart DA: Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. Epub 2004 May 24. [PubMed:15159443]
  5. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [PubMed:12124303]
  6. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Desta Z, Ward BA, Soukhova NV, Flockhart DA: Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. Epub 2004 May 24. [PubMed:15159443]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Desta Z, Ward BA, Soukhova NV, Flockhart DA: Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. Epub 2004 May 24. [PubMed:15159443]
  2. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [PubMed:12124303]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Details
7. Cytochrome P450 2B6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Desta Z, Ward BA, Soukhova NV, Flockhart DA: Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75. Epub 2004 May 24. [PubMed:15159443]
  2. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [PubMed:12124303]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [PubMed:12124303]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [PubMed:12124303]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM: Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. [PubMed:12124303]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Nadp binding
Specific Function
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name
FMO1
Uniprot ID
Q01740
Uniprot Name
Dimethylaniline monooxygenase [N-oxide-forming] 1
Molecular Weight
60310.285 Da
References
  1. Krueger SK, Vandyke JE, Williams DE, Hines RN: The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines. Drug Metab Rev. 2006;38(1-2):139-47. [PubMed:16684653]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Trimethylamine monooxygenase activity
Specific Function
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an impor...
Gene Name
FMO3
Uniprot ID
P31513
Uniprot Name
Dimethylaniline monooxygenase [N-oxide-forming] 3
Molecular Weight
60032.975 Da
References
  1. Krueger SK, Vandyke JE, Williams DE, Hines RN: The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines. Drug Metab Rev. 2006;38(1-2):139-47. [PubMed:16684653]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Fleming CD, Bencharit S, Edwards CC, Hyatt JL, Tsurkan L, Bai F, Fraga C, Morton CL, Howard-Williams EL, Potter PM, Redinbo MR: Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. J Mol Biol. 2005 Sep 9;352(1):165-77. [PubMed:16081098]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein kinase c binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A10
Uniprot ID
Q9HAW8
Uniprot Name
UDP-glucuronosyltransferase 1-10
Molecular Weight
59809.075 Da
References
  1. Sun D, Sharma AK, Dellinger RW, Blevins-Primeau AS, Balliet RM, Chen G, Boyiri T, Amin S, Lazarus P: Glucuronidation of active tamoxifen metabolites by the human UDP glucuronosyltransferases. Drug Metab Dispos. 2007 Nov;35(11):2006-14. Epub 2007 Jul 30. [PubMed:17664247]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estroge...
Gene Name
SULT1A1
Uniprot ID
P50225
Uniprot Name
Sulfotransferase 1A1
Molecular Weight
34165.13 Da
References
  1. Wegman P, Elingarami S, Carstensen J, Stal O, Nordenskjold B, Wingren S: Genetic variants of CYP3A5, CYP2D6, SULT1A1, UGT2B15 and tamoxifen response in postmenopausal patients with breast cancer. Breast Cancer Res. 2007;9(1):R7. [PubMed:17244352]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Riley J, Styles J, Verschoyle RD, Stanley LA, White IN, Gant TW: Association of tamoxifen biliary excretion rate with prior tamoxifen exposure and increased mdr1b expression. Biochem Pharmacol. 2000 Jul 15;60(2):233-9. [PubMed:10825468]
  2. Bekaii-Saab TS, Perloff MD, Weemhoff JL, Greenblatt DJ, von Moltke LL: Interactions of tamoxifen, N-desmethyltamoxifen and 4-hydroxytamoxifen with P-glycoprotein and CYP3A. Biopharm Drug Dispos. 2004 Oct;25(7):283-9. [PubMed:15386482]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. [PubMed:12668685]
Details
3. Bile salt export pump
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Kiyotani K, Mushiroda T, Imamura CK, Hosono N, Tsunoda T, Kubo M, Tanigawara Y, Flockhart DA, Desta Z, Skaar TC, Aki F, Hirata K, Takatsuka Y, Okazaki M, Ohsumi S, Yamakawa T, Sasa M, Nakamura Y, Zembutsu H: Significant effect of polymorphisms in CYP2D6 and ABCC2 on clinical outcomes of adjuvant tamoxifen therapy for breast cancer patients. J Clin Oncol. 2010 Mar 10;28(8):1287-93. doi: 10.1200/JCO.2009.25.7246. Epub 2010 Feb 1. [PubMed:20124171]

Drug created on June 13, 2005 07:24 / Updated on December 04, 2017 13:13