Identification

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

Tamoxifen is a non-steroidal antiestrogen used to treat estrogen receptor positive breast cancers as well as prevent the incidence of breast cancer in high risk populations.1,15,16 Tamoxifen is used alone or as an adjuvant in these treatments.15,16 Tamoxifen may no longer be the preferred treatment for these types of cancers as patients generally have better survival, side effect profiles, and compliance with anastrozole.2

Tamoxifen was granted FDA approval on 30 December 1977.15

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
  • Tamoxifen
  • Tamoxifène
  • Tamoxifene
  • Tamoxifeno
  • Tamoxifenum
  • trans-Tamoxifen
External IDs
ICI 47699 / ICI-47699
Product Ingredients
IngredientUNIICASInChI Key
Tamoxifen citrate7FRV7310N654965-24-1FQZYTYWMLGAPFJ-OQKDUQJOSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NolvadexTablet20 mg/1OralAstra Zeneca Lp1994-03-312008-03-31Us
NolvadexTablet10 mg/1OralAstra Zeneca Lp1990-09-012008-03-31Us
Nolvadex Tab 10mgTabletOralAstra Zeneca1994-12-312003-04-01Canada
Nolvadex-D Tab 20mgTabletOralAstra Zeneca1995-12-31Not applicableCanada
SoltamoxLiquid20 mg/10mLOralMidatech Pharma Us Inc.2005-10-29Not applicableUs
SoltamoxLiquid10 mg/5mLOralRosemont Pharmaceuticals Ltd2012-10-01Not applicableUs
Tamofen 10TabletOralSanofi Aventis1986-12-312011-01-11Canada
Tamofen 20TabletOralSanofi Aventis1986-12-312011-01-14Canada
Tamone - (10 Mg)TabletOralPfizer Canada Ulc1996-12-312007-10-02Canada
Tamone - (20 Mg)TabletOralPfizer Canada Ulc1996-12-312007-10-02Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tamox Tab 10mgTabletOralApotex Corporation1989-12-31Not applicableCanada
Apo-tamox Tab 20mgTabletOralApotex Corporation1989-12-31Not applicableCanada
Dom-tamoxifenTabletOralDominion PharmacalNot applicableNot applicableCanada
Dom-tamoxifenTabletOralDominion PharmacalNot applicable2016-10-25Canada
Mylan-tamoxifenTabletOralMylan Pharmaceuticals1994-12-312017-01-09Canada
Mylan-tamoxifenTabletOralMylan Pharmaceuticals1994-12-312017-01-09Canada
Penta-tamoxifen TabletsTabletOralPentapharm Ltd.Not applicableNot applicableCanada
Penta-tamoxifen TabletsTabletOralPentapharm Ltd.Not applicableNot applicableCanada
PMS-tamoxifenTabletOralPharmascience Inc1998-12-012016-10-28Canada
PMS-tamoxifenTabletOralPharmascience Inc1998-12-012016-10-28Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
NuvyaTamoxifen citrate (0.1 g/0.1g) + Adapalene (0.15 g/0.15g) + Diclofenac sodium (1 g/1g)KitTopicalAccumix Pharmaceuticals2014-12-152015-07-17Us
International/Other Brands
Adifen (Medicamerc) / Adopan (Sawai Seiyaku) / Bilem (Teva Int'l) / Caditam (Cadila) / Citofen / Crisafeno (LKM) / Doctamoxifene (Docpharma) / Ebefen (Ebewe) / Fenahex (Sandoz) / Genox (Merck Serono) / Gynatam (Biogalenic) / Istubal (AstraZeneca) / Mammonex (CP Pharmaceuticals) / Neophedan (Aspen Pharmacare) / Noltam / Nolvadex-D (AstraZeneca) / Novofen (Remedica) / Oncomox (Sun) / Tadex (Orion) / Tamifen (Medochemie) / Tamizam (Mithra) / Tamofen (Sanofi-Aventis) / 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 to treat estrogen receptor positive metastatic breast cancer in adults, as an adjuvant in the treatment of early stage estrogen receptor positive breast cancer in adults, to reduce the risk of invasive breast cancer after surgery and radiation in adult women with ductal carcinoma in situ.16

Associated Conditions
Associated Therapies
Pharmacodynamics

Tamoxifen is a selective estrogen receptor modulator that inhibits growth and promotes apoptosis in estrogen receptor positive tumors.1,8 It has a long duration of action as the active metabolite N-desmethyltamoxifen has a half life of approximately 2 weeks.15,16 It has a narrow therapeutic index as higher doses can lead to breathing difficulty or convulsions.15,16 Tamoxifen administration is also associated with an increased incidence of uterine malignancies.15,16

Mechanism of action

Tamoxifen competitively inhibits estrogen binding to its receptor, which is critical for it's activity in breast cancer cells.1 Tamoxifen leads to a decrease in tumor growth factor α and insulin-like growth factor 1, and an increase in sex hormone binding globulin.1 The increase in sex hormon binding globulin limits the amount of freely available estradiol.1 These changes reduce levels of factors that stimulate tumor growth.1

Tamoxifen has also been shown to induce apoptosis in estrogen receptor positive cells.8 This action is thought to be the result of inhibition of protein kinase C, which prevents DNA synthesis.8 Alternate theories for the apoptotic effect of tamoxifen comes from the approximately 3 fold increase in intracellular and mitochondrial calcium ion levels after administration or the induction of tumor growth factor β.8

TargetActionsOrganism
AEstrogen receptor alpha
antagonist
agonist
Humans
AEstrogen receptor beta
antagonist
agonist
Humans
U3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase
inhibitor
Humans
AProtein kinase C
inhibitor
Humans
UAndrogen receptorNot AvailableHumans
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
UEstrogen-related receptor gammaNot AvailableHumans
ASex hormone-binding globulin
inducer
Humans
UMitogen-activated protein kinase 8
modulator
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

An oral dose of 20mg reaches a Cmax of 40ng/mL with a Tmax of 5 hours.15,16 The metabolite N-desmethyltamoxifen reaches a Cmax of 15ng/mL.15,16 10mg of tamoxifen orally twice daily for 3 months results in a Css of 120ng/mL and a Css of 336ng/mL.15,16

Volume of distribution

The volume of distribution of tamoxifen is approximately 50-60L/kg.11

Protein binding

The protein binding of tamoxifen in plasma is over 98% and mostly to serum albumin.11

Metabolism

Tamoxifen can by hydroxylated to α-hydroxytamoxifen which is then glucuronidated or undergoes sulfate conjugation by sulfotransferase 2A1.4,6 Tamoxifen can also undergo N-oxidation by flavin monooxygenases 1 and 3 to tamoxifen N-oxide.4,6,7 Tamoxifen is N-dealkylated to N-desmethyltamoxifen by CYP2D6, CYP1A1, CYP1A2, CYP3A4, CYP1B1, CYP2C9, CYP2C19, and CYP3A5.3,4,5,6,7 N-desmethyltamoxifen can be sulfate conjugated to form N-desmethyltamoxifen sulfate, 4-hydroxylated by CYP2D6 to form endoxifen, or N-dealkylated again by CYP3A4 and CYP3A5 to N,N-didesmethyltamoxifen.4,5,13 N,N-didesmethyltamoxifen undergoes a substitution reaction to form tamoxifen metabolite Y, followed by ether cleavage to metabolite E, which can then be sulfate conjugated by sulfotransferase 1A1 and 1E1 or O-glucuronidated.13,14

Tamoxifen can also by 4-hydroxylated by CYP2D6, CYP2B6, CYP3A4, CYP2C9, and CYP2C19 to form 4-hydroxytamoxifen.3,4,5,6 4-hydroxytamoxifen can undergo glucuronidation by UGT1A8, UGT1A10, UGT2B7, and UGT2B17 to tamoxifen glucuronides, sulfate conjugation by sulfotransferase 1A1 and 1E1 to 4-hydroxytamoxifen sulfate, or N-dealkylation by CYP3A4 and CYP3A5 to endoxifen.4,5

Endoxifen undergoes demethylation to norendoxifen, a reversible sulfate conjugation reaction via sulfotransferase 1A1 and 1E1 to 4-hydroxytamoxifen sulfate, sulfate conjugation via sulfotransferase 2A1 to 4-endoxifen sulfate, or glucuronidation via UGT1A8, UGT1A10, UGT2B7, or UGT2B15 to tamoxifen glucuronides.13,4,5

Route of elimination

Tamoxifen is mainly eliminated in the feces.15,16 Animal studies have shown 75% of radiolabelled tamoxifen recovered in the feces, with negligible collection from urine.9 However, 1 human study showed 26.7% recovery in the urine and 24.7% in the feces.10

Half life

The terminal elimination half life of tamoxifen is 5 to 7 days, while the half life of N-desmethyltamoxifen, the primary circulating metabolite, is approximately 14 days.15,16

Clearance

The clearance of tamoxifen was 189mL/min in a study of six postmenopausal women.12

Toxicity

High doses of tamoxifen in animals lead to respiratory difficulty and convulsions.15,16 High doses in advanced metastatic cancer patients resulted in acute neurotoxicity seen by tremor, hyperreflexia, unsteady gait, and dizziness.15,16 Patients experiencing and overdose should be given supportive treatment as no specific treatment for overdose is suggested.15,16

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tamoxifen Metabolism PathwayDrug metabolism
Tamoxifen Action PathwayDrug action
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Tamoxifen is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Tamoxifen is combined with (S)-Warfarin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Tamoxifen can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Tamoxifen is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Tamoxifen.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Tamoxifen.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Tamoxifen.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Tamoxifen.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be increased when combined with Tamoxifen.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Tamoxifen.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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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: 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]
  2. 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]
  3. 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]
  4. Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. [PubMed:25157097]
  5. Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. [PubMed:24328412]
  6. White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. [PubMed:10383884]
  7. Parte P, Kupfer D: Oxidation of tamoxifen by human flavin-containing monooxygenase (FMO) 1 and FMO3 to tamoxifen-N-oxide and its novel reduction back to tamoxifen by human cytochromes P450 and hemoglobin. Drug Metab Dispos. 2005 Oct;33(10):1446-52. doi: 10.1124/dmd.104.000802. Epub 2005 Jun 29. [PubMed:15987777]
  8. Radin DP, Patel P: Delineating the molecular mechanisms of tamoxifen's oncolytic actions in estrogen receptor-negative cancers. Eur J Pharmacol. 2016 Jun 15;781:173-80. doi: 10.1016/j.ejphar.2016.04.017. Epub 2016 Apr 12. [PubMed:27083550]
  9. Fromson JM, Pearson S, Bramah S: The metabolism of tamoxifen (I.C.I. 46,474). I. In laboratory animals. Xenobiotica. 1973 Nov;3(11):693-709. doi: 10.3109/00498257309151594. [PubMed:4361333]
  10. Kisanga ER, Mellgren G, Lien EA: Excretion of hydroxylated metabolites of tamoxifen in human bile and urine. Anticancer Res. 2005 Nov-Dec;25(6C):4487-92. [PubMed:16334131]
  11. Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, Ueland PM: Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res. 1989 Apr 15;49(8):2175-83. [PubMed:2702659]
  12. Lien EA, Anker G, Lonning PE, Solheim E, Ueland PM: Decreased serum concentrations of tamoxifen and its metabolites induced by aminoglutethimide. Cancer Res. 1990 Sep 15;50(18):5851-7. [PubMed:2393854]
  13. Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE: PharmGKB summary: tamoxifen pathway, pharmacokinetics. Pharmacogenet Genomics. 2013 Nov;23(11):643-7. doi: 10.1097/FPC.0b013e3283656bc1. [PubMed:23962908]
  14. Kemp JV, Adam HK, Wakeling AE, Slater R: Identification and biological activity of tamoxifen metabolites in human serum. Biochem Pharmacol. 1983 Jul 1;32(13):2045-52. doi: 10.1016/0006-2952(83)90425-2. [PubMed:6870933]
  15. FDA Approved Drug Products: Tamoxifen Oral Tablets [Link]
  16. FDA Approved Drug Products: Tamoxifen Oral Solution [Link]
External Links
Human Metabolome Database
HMDB0014813
KEGG Drug
D08559
KEGG Compound
C07108
PubChem Compound
2733526
PubChem Substance
46505515
ChemSpider
2015313
BindingDB
20607
ChEBI
41774
ChEMBL
CHEMBL83
Therapeutic Targets Database
DAP000108
PharmGKB
PA451581
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 / 6ohu
FDA label
Download (102 KB)
MSDS
Download (74.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
0TerminatedPreventionBarrett's Metaplasia1
1Active Not RecruitingTreatmentBreast Cancer / Breast Cancer - Female / Breast Cancer - Male1
1Active Not RecruitingTreatmentDuchenne's Muscular Dystrophy (DMD)1
1Active Not RecruitingTreatmentHormone Receptor Positive, HER2-negative, Advanced Breast Cancer1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceTumors, Solid1
1CompletedTreatmentBreast Cancer4
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentNeoplasms Metastasis / Sarcoma, Osteogenic1
1CompletedTreatmentOvarian Cancer1
1CompletedTreatmentTumors, Solid1
1Not Yet RecruitingBasic ScienceMalignancies / Neoplasms, Gastrointestinal1
1Not Yet RecruitingTreatmentAnatomic Stage III Breast Cancer AJCC v8 / Anatomic Stage IIIA Breast Cancer AJCC v8 / Anatomic Stage IIIB Breast Cancer AJCC v8 / Anatomic Stage IIIC Breast Cancer AJCC v8 / Anatomic Stage IV Breast Cancer AJCC v8 / Estrogen Receptor Positive / HER2/Neu Negative / Invasive Breast Carcinoma / Prognostic Stage III Breast Cancer AJCC v8 / Prognostic Stage IIIA Breast Cancer AJCC v8 / Prognostic Stage IIIB Breast Cancer AJCC v8 / Prognostic Stage IIIC Breast Cancer AJCC v8 / Prognostic Stage IV Breast Cancer AJCC v8 / Recurrent Breast Carcinoma1
1RecruitingOtherBreast Cancer1
1RecruitingTreatmentNeoplasms, Breast1
1Unknown StatusTreatmentBreast Cancer1
1, 2CompletedPreventionBreast Cancer / Mammographic Density1
1, 2CompletedTreatmentALS Functional Ration Scale / Amyotrophic Lateral Sclerosis (ALS) / MTOR / Tamoxifen / TAR-DNA-binding Protein-431
1, 2RecruitingTreatmentBreast Cancer / Cancer of the Uterus / Ovarian Cancer1
1, 2RecruitingTreatmentNeoplasms, Breast1
1, 2TerminatedTreatmentBreast Cancer / Neoplasms, Breast / Tumors, Breast1
2Active Not RecruitingBasic ScienceBreast Cancer1
2Active Not RecruitingPreventionBreast Cancer1
2Active Not RecruitingPreventionMammographic Density Reduction / Risk Reduction1
2Active Not RecruitingTreatmentAdvanced, Persistent, or Recurrent Endometrial Cancer1
2Active Not RecruitingTreatmentBreast Cancer6
2Active Not RecruitingTreatmentBreast Cancer / Stage II Breast Cancer / Stage III Breast Cancer1
2Active Not RecruitingTreatmentErectile Dysfunction / 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 RecruitingTreatmentMetastatic Breast Cancer1
2Active Not RecruitingTreatmentNeoplasms, Breast2
2Active Not RecruitingTreatmentReccurent/Metastatic Solid Tumor Disease1
2CompletedNot AvailableAmyotrophic Lateral Sclerosis (ALS)1
2CompletedPreventionBreast Cancer2
2CompletedPreventionBreast Cancer / Hereditary Breast/Ovarian Cancer (brca1, brca2)1
2CompletedSupportive CareBreast Cancer / 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
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentBipolar Disorder (BD) / Mania / Schizoaffective Disorders1
2CompletedTreatmentBleeding / Breakthrough Bleeding / Implants1
2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentBrain and Central Nervous System Tumors / Metastatic Cancers / Unspecified Adult Solid Tumor, Protocol Specific1
2CompletedTreatmentBreast Cancer14
2CompletedTreatmentBreast Cancer / Neoplasms, Breast2
2CompletedTreatmentBreast Fibroadenoma1
2CompletedTreatmentCancer of the Fallopian Tube / Malignant Peritoneal Neoplasm / Ovarian Cancer1
2CompletedTreatmentDesmoid Tumors1
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 Breast 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 Cancer3
2CompletedTreatmentNeoplasms, Breast4
2CompletedTreatmentMTor Protein / Neoplasms, Breast1
2CompletedTreatmentNewly Diagnosed Hormone Positive Clinical Stage 1 or 2 Breast Cancer1
2CompletedTreatmentUrinary Bladder Neoplasms1
2Not Yet RecruitingOtherBreast Cancer1
2Not Yet RecruitingTreatmentBreast Cancer / Breast Cancer Stage II / Breast Cancer Stage III / Her2-Positive Breast Cancer / Malignant Neoplasm of Female Breast1
2Not Yet RecruitingTreatmentHormone Receptor Positive Tumor / Malignant Neoplasm of Female Breast1
2Not Yet RecruitingTreatmentMalignant Neoplasm of Female Breast1
2RecruitingBasic ScienceBreast Cancer2
2RecruitingOtherBreast Cancer1
2RecruitingScreeningNon Metastatic Breast Cancer1
2RecruitingTreatmentAnatomic Stage IV Breast Cancer AJCC v8 / Estrogen Receptor Positive / HER2/Neu Negative / Metastatic Breast Carcinoma / Metastatic Malignant Neoplasm in the Bone / Progesterone Receptor Positive / Prognostic Stage IV Breast Cancer AJCC v81
2RecruitingTreatmentBladder Cancers2
2RecruitingTreatmentBreast Cancer3
2RecruitingTreatmentBreast Cancer / Breast Cancer Invasive Nos1
2RecruitingTreatmentBreast Cancer / Cancer of the Breast / Neoplasms, Breast1
2RecruitingTreatmentBreast Cancer / Estrogen Receptor-Positive Breast Cancer1
2RecruitingTreatmentChronic Lung Diseases / Estrogen Receptor Antagonist / Estrogens / Familial Primary Pulmonary Hypertension / High Blood Pressure (Hypertension) / Hormone Antagonists / Primary Pulmonary Hypertension / Pulmonary Arterial Hypertension (PAH) / Tamoxifen1
2RecruitingTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor Positive1
2RecruitingTreatmentEarly Breast Cancer / Hormone Receptor Positive Tumor1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Estrogen Receptor Positive Tumor1
2RecruitingTreatmentEarly-Stage Breast Carcinoma / Hormone Receptor Positive Tumor1
2RecruitingTreatmentEstrogen Receptor Positive Breast Cancer / Hormone Receptor Positive Malignant Neoplasm of Breast / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Metastatic Breast Cancer / Progesterone Receptor Positive Tumor1
2RecruitingTreatmentEstrogen Receptor Positive Tumor / Neuroendocrine Tumors / Progesterone Receptor Positive Tumor2
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Meningitis / Meningitis streptococcal / Meningoencephalitis1
2RecruitingTreatmentMetastatic Breast Cancer2
2RecruitingTreatmentNeoplasms, Breast2
2RecruitingTreatmentOvarian Carcinoma1
2RecruitingTreatmentUterine Cervical Neoplasms1
2TerminatedBasic ScienceBreast Cancer Invasive Nos / Early Breast Cancer / Stage II Breast Cancer / Stage III Breast Cancer1
2TerminatedPreventionBreast Cancer1
2TerminatedTreatmentBiochemical-recurrent Only Epithelial Ovarian Cancer / Fallopian Tube Cancer / Genitourinary (GU) Tumors / GU (Genitourinary) Tumors / Ovarian Cancer / Primary Peritoneal Carcinoma1
2TerminatedTreatmentBreast Cancer2
2TerminatedTreatmentBreast Cancer / Metastatic Disease1
2TerminatedTreatmentCarcinoma, Breast1
2TerminatedTreatmentMetastatic Breast Cancer / One to five years postmenopausal1
2TerminatedTreatmentNeoplasms, Breast1
2Unknown StatusDiagnosticFallopian Tube Cancer / Ovarian Cancer / Primary Peritoneal Cavity Cancer1
2Unknown StatusTreatmentBrain and Central Nervous System Tumors2
2Unknown StatusTreatmentBreast Cancer3
2Unknown StatusTreatmentIntraocular Melanoma1
2Unknown StatusTreatmentMelanoma (Skin)1
2Unknown StatusTreatmentRetroperitoneal Fibrosis1
2WithdrawnTreatmentBreast Cancer / Breast Cancer Stage II / Breast Cancer Stage III1
2, 3Active Not RecruitingTreatmentLow Grade Ovarian Serous Adenocarcinoma / Micropapillary Serous Carcinoma / Ovarian Serous Adenocarcinoma / Primary Peritoneal Serous Adenocarcinoma / Recurrent Low Grade Ovarian Serous Adenocarcinoma / Recurrent Ovarian Carcinoma / Recurrent Primary Peritoneal Carcinoma / Recurrent Primary Peritoneal Serous Adenocarcinoma1
2, 3Not Yet RecruitingPreventionDiscomfort / Pain1
2, 3Not Yet RecruitingTreatmentBreast Cancer1
2, 3Not Yet RecruitingTreatmentBreast Cancer / Cancer treatment / Endocrine Breast Diseases1
2, 3RecruitingTreatmentBreast Cancer Patients in Premenopausal / Estrogen and/or Progesterone Receptor Positive1
2, 3TerminatedTreatmentBreast Cancer1
3Active Not RecruitingPreventionBreast Cancer2
3Active Not RecruitingPreventionIntraepithelial Carcinoma1
3Active Not RecruitingTreatmentAdvanced Metastatic Breast Cancer / Advanced, 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 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 IIIA Breast Cancer / Stage IIIA Breast Cancer AJCC v71
3Active Not RecruitingTreatmentBreast Cancer6
3Active Not RecruitingTreatmentBreast Cancer / 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 RecruitingTreatmentDuctal Breast Carcinoma In Situ / Estrogen Receptor and/or Progesterone Receptor Positive / Estrogen Receptor Positive / HER2/Neu Negative / Invasive Breast Carcinoma / Multicentric Breast Carcinoma / Multifocal Breast Carcinoma / Progesterone Receptor Positive / Synchronous Bilateral Breast Carcinoma1
3Active Not RecruitingTreatmentEstrogen Receptor Positive / Invasive Breast Carcinoma / One to five years postmenopausal / Progesterone Receptor Positive / Recurrent Breast Carcinoma / Stage III Breast Cancer AJCC v6 / Stage IIIB Breast Cancer / Stage IIIB Breast Cancer AJCC v7 / Stage IV Breast Cancer / Stage IV Breast Cancer AJCC v6 and v71
3Active Not RecruitingTreatmentNeoplasms, Breast1
3CompletedNot AvailableBone Density1
3CompletedNot AvailableBreast Cancer1
3CompletedNot AvailableBreast Cancer / Fatigue / Sleep disorders and disturbances1
3CompletedNot AvailablePrimary Breast Cancer1
3CompletedNot AvailableQuality of Life1
3CompletedPreventionAging / Cognition1
3CompletedPreventionBreast Cancer1
3CompletedPreventionBreast Cancer / Endometrial Cancer1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Ischemia1
3CompletedPreventionProstate Cancer1
3CompletedTreatmentBipolar Disorder (BD)1
3CompletedTreatmentBreast Cancer36
3CompletedTreatmentBreast Cancer / Cyclophosphamide / Doxorubicin / High Risk / Positive Nodes1
3CompletedTreatmentBreast Cancer / Metastasis1
3CompletedTreatmentCancer of the Fallopian Tube / Malignant Peritoneal Neoplasm / Ovarian Cancer1
3CompletedTreatmentEarly 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
3CompletedTreatmentMale Breast Cancer1
3CompletedTreatmentNeoplasms, Breast4
3Enrolling by InvitationTreatmentCYP2D6 Polymorphism1
3Not Yet RecruitingTreatmentOvarian Carcinoma / Signal Transduction Pathway Deregulation / Therapy-Associated Cancer1
3RecruitingTreatmentBreast Cancer4
3RecruitingTreatmentDuchenne's Muscular Dystrophy (DMD)1
3RecruitingTreatmentInfertilities1
3RecruitingTreatmentMalignant Neoplasm of Female Breast1
3TerminatedTreatmentBreast Cancer3
3TerminatedTreatmentCardiac Toxicity / Inflammatory carcinoma of the breast / Stage IIIA Breast Cancer / Stage IIIB Breast Cancer / Stage IV Breast Cancer1
3TerminatedTreatmentEndometrial Cancer1
3TerminatedTreatmentMammographic Breast Density1
3Unknown StatusTreatmentBreast Cancer13
3Unknown StatusTreatmentBreast Cancer / Pulmonary Fibrosis1
3WithdrawnTreatmentRecurrent Breast Cancer / Stage IV Breast Cancer1
4CompletedNot AvailableBreast Cancer1
4CompletedBasic SciencePharmacokinetics1
4CompletedHealth Services ResearchBreast Cancer1
4CompletedPreventionHypermenorrhea / Medicated Intrauterine Devices / Metrorrhagia1
4CompletedSupportive CarePolycystic Ovarian Syndrome1
4CompletedTreatmentBenign Breast Disease / Breast Pain / Fibroadenoma / Fibrocystic Disease of Breast1
4CompletedTreatmentBreast Cancer3
4CompletedTreatmentHormono-depending Adjuvant Breast Cancer1
4CompletedTreatmentMenstruation Disturbances1
4Not Yet RecruitingTreatmentEndometrium1
4Not Yet RecruitingTreatmentInfertilities1
4RecruitingTreatmentBreast Cancer1
4RecruitingTreatmentEarly Breast Cancer1
4RecruitingTreatmentMetastatic Breast Cancer1
4RecruitingTreatmentSexuality1
4WithdrawnTreatmentHER2/Neu Negative / Invasive Breast Carcinoma / One to five years postmenopausal / Stage 0 Breast Cancer / Stage IA Breast Cancer1
Not AvailableActive Not RecruitingNot AvailableBreast Cancer / Depression / Hot Flushes / Psychosocial Effects of Cancer and Its Treatment1
Not AvailableActive Not RecruitingHealth Services ResearchBreast Cancer1
Not AvailableCompletedNot AvailableAntineoplastic Agents / Neoplasms, Breast / Survival Analysis / Therapeutic Uses1
Not AvailableCompletedNot AvailableBMI >30 kg/m2 / Breast Cancer / Joint Pain1
Not AvailableCompletedNot AvailableBreast Cancer1
Not AvailableCompletedBasic ScienceHigh Background Uptake on MBI1
Not AvailableCompletedDiagnosticBreast Cancer / CYP2D6 Polymorphism1
Not AvailableCompletedPreventionBreast Cancer / Hodgkins Disease (HD)1
Not AvailableCompletedTreatmentBreast Cancer2
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 AvailableCompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Metastatic Breast Cancer / Sarcomas / Tumors, Solid1
Not AvailableNot Yet RecruitingNot AvailableBreast Cancer2
Not AvailableNot Yet RecruitingNot AvailableRecurrent Endometrial Cancer / Stage III Endometrial Cancer / Stage IV Endometrial Cancer1
Not AvailableRecruitingNot AvailableBreast Cancer / Sleep Disorder1
Not AvailableRecruitingNot AvailableHR+ HER2- Men, Pre/Postmenopausal Advanced Breast Cancer / HR+ HER2- Postmenopausal Advanced Breast Cancer1
Not AvailableRecruitingTreatmentBreast Cancer1
Not AvailableRecruitingTreatmentBreast Cancer Nos Premenopausal1
Not AvailableTerminatedNot AvailableBreast Cancer2
Not AvailableUnknown StatusNot AvailableCYP2D6 / Genotyping / Neoplasms, Breast / Tamoxifen1
Not AvailableUnknown StatusTreatmentBreast Cancer1
Not AvailableUnknown StatusTreatmentBreast Cancer / 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
  • Amerisource Health Services Corp.
  • AQ Pharmaceuticals Inc.
  • AstraZeneca Inc.
  • Barr Pharmaceuticals
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Egis Pharmaceuticals Public Ltd. Co.
  • Imperial Chemical Industrial Ltd.
  • Innovative Manufacturing and Distribution Services Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Mckesson Corp.
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Ranbaxy Laboratories
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Wampole Laboratories
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral
KitTopical
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)
US6127425No2000-10-032018-06-26Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)97 °Chttp://www.chemspider.com/Chemical-Structure.2015313.html?rid=1b2fa2ba-dc6c-450e-bcf7-467741bd4eb1
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
Humans
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
Humans
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
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
Humans
Pharmacological action
Yes
Actions
Inhibitor
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]
  2. Radin DP, Patel P: Delineating the molecular mechanisms of tamoxifen's oncolytic actions in estrogen receptor-negative cancers. Eur J Pharmacol. 2016 Jun 15;781:173-80. doi: 10.1016/j.ejphar.2016.04.017. Epub 2016 Apr 12. [PubMed:27083550]
Kind
Protein
Organism
Humans
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
Humans
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
Humans
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
Humans
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
Humans
Pharmacological action
Yes
Actions
Inducer
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]
  2. Radin DP, Patel P: Delineating the molecular mechanisms of tamoxifen's oncolytic actions in estrogen receptor-negative cancers. Eur J Pharmacol. 2016 Jun 15;781:173-80. doi: 10.1016/j.ejphar.2016.04.017. Epub 2016 Apr 12. [PubMed:27083550]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Modulator
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine-protein kinase involved in various processes such as cell proliferation, differentiation, migration, transformation and programmed cell death. Extracellular stimuli such as proinfl...
Gene Name
MAPK8
Uniprot ID
P45983
Uniprot Name
Mitogen-activated protein kinase 8
Molecular Weight
48295.14 Da
References
  1. Radin DP, Patel P: Delineating the molecular mechanisms of tamoxifen's oncolytic actions in estrogen receptor-negative cancers. Eur J Pharmacol. 2016 Jun 15;781:173-80. doi: 10.1016/j.ejphar.2016.04.017. Epub 2016 Apr 12. [PubMed:27083550]

Enzymes

Kind
Protein
Organism
Humans
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. Flockhart Table of Drug Interactions [Link]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
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. 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]
  3. Zhao XJ, Jones DR, Wang YH, Grimm SW, Hall SD: Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica. 2002 Oct;32(10):863-78. doi: 10.1080/00498250210158230 . [PubMed:12419016]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. Zhao XJ, Jones DR, Wang YH, Grimm SW, Hall SD: Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica. 2002 Oct;32(10):863-78. doi: 10.1080/00498250210158230 . [PubMed:12419016]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. Boruban MC, Yasar U, Babaoglu MO, Sencan O, Bozkurt A: Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4. doi: 10.1179/joc.2006.18.4.421. [PubMed:17024799]
  2. Saladores P, Murdter T, Eccles D, Chowbay B, Zgheib NK, Winter S, Ganchev B, Eccles B, Gerty S, Tfayli A, Lim JS, Yap YS, Ng RC, Wong NS, Dent R, Habbal MZ, Schaeffeler E, Eichelbaum M, Schroth W, Schwab M, Brauch H: Tamoxifen metabolism predicts drug concentrations and outcome in premenopausal patients with early breast cancer. Pharmacogenomics J. 2015 Feb;15(1):84-94. doi: 10.1038/tpj.2014.34. Epub 2014 Aug 5. [PubMed:25091503]
  3. Tamoxifen FDA label [File]
Kind
Protein
Organism
Humans
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]
Details
7. Cytochrome P450 2B6
Kind
Protein
Organism
Humans
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. Hedrich WD, Hassan HE, Wang H: Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. doi: 10.1016/j.apsb.2016.07.016. Epub 2016 Aug 9. [PubMed:27709010]
  4. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
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. Zhao XJ, Jones DR, Wang YH, Grimm SW, Hall SD: Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica. 2002 Oct;32(10):863-78. doi: 10.1080/00498250210158230 . [PubMed:12419016]
Kind
Protein
Organism
Humans
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
Humans
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
Humans
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. Jernstrom H, Bageman E, Rose C, Jonsson PE, Ingvar C: CYP2C8 and CYP2C9 polymorphisms in relation to tumour characteristics and early breast cancer related events among 652 breast cancer patients. Br J Cancer. 2009 Dec 1;101(11):1817-23. doi: 10.1038/sj.bjc.6605428. [PubMed:19935798]
Kind
Protein
Organism
Humans
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
Humans
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. Fiorelli G, Picariello L, Martineti V, Tonelli F, Brandi ML: Estrogen synthesis in human colon cancer epithelial cells. J Steroid Biochem Mol Biol. 1999 Dec 31;71(5-6):223-30. [PubMed:10704911]
Kind
Protein
Organism
Humans
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. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
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. Styles JA, Davies A, Lim CK, De Matteis F, Stanley LA, White IN, Yuan ZX, Smith LL: Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9. doi: 10.1093/carcin/15.1.5. [PubMed:8293548]
Kind
Protein
Organism
Humans
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
Humans
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]
Kind
Protein
Organism
Humans
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 sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name
SULT2A1
Uniprot ID
Q06520
Uniprot Name
Bile salt sulfotransferase
Molecular Weight
33779.57 Da
References
  1. Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. [PubMed:25157097]
  2. White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. [PubMed:10383884]
Kind
Protein
Organism
Humans
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]
  2. Squirewell EJ, Qin X, Duffel MW: Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50. doi: 10.1124/dmd.114.059709. Epub 2014 Aug 25. [PubMed:25157097]
  3. Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. [PubMed:24328412]
  4. White IN: The tamoxifen dilemma. Carcinogenesis. 1999 Jul;20(7):1153-60. doi: 10.1093/carcin/20.7.1153. [PubMed:10383884]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. [PubMed:24328412]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbe...
Gene Name
UGT2B17
Uniprot ID
O75795
Uniprot Name
UDP-glucuronosyltransferase 2B17
Molecular Weight
61094.915 Da
References
  1. Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. [PubMed:24328412]
Kind
Protein
Organism
Humans
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 estradiol and estrone. May play a role in the regulation of estrogen r...
Gene Name
SULT1E1
Uniprot ID
P49888
Uniprot Name
Estrogen sulfotransferase
Molecular Weight
35126.185 Da
References
  1. Cronin-Fenton DP, Damkier P, Lash TL: Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22. doi: 10.2217/fon.13.168. [PubMed:24328412]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, Ueland PM: Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res. 1989 Apr 15;49(8):2175-83. [PubMed:2702659]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Serine-type endopeptidase inhibitor activity
Specific Function
Major thyroid hormone transport protein in serum.
Gene Name
SERPINA7
Uniprot ID
P05543
Uniprot Name
Thyroxine-binding globulin
Molecular Weight
46324.12 Da
References
  1. CYTOMEL (liothyronine) FDA label [File]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
Curator comments
Induces MDR1 expression but inhibits transporter action.
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
Humans
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]
Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Wilson A. (2016). New horizons in predictive drug metabolism and pharmacokinetics. The Royal Society of Chemistry. [ISBN:978-1-84973-828-6]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Syntaxin binding
Specific Function
cAMP-dependent and sulfonylurea-sensitive anion transporter. Key gatekeeper influencing intracellular cholesterol transport.
Gene Name
ABCA1
Uniprot ID
O95477
Uniprot Name
ATP-binding cassette sub-family A member 1
Molecular Weight
254299.89 Da
References
  1. Klein DJ, Thorn CF, Desta Z, Flockhart DA, Altman RB, Klein TE: PharmGKB summary: tamoxifen pathway, pharmacokinetics. Pharmacogenet Genomics. 2013 Nov;23(11):643-7. doi: 10.1097/FPC.0b013e3283656bc1. [PubMed:23962908]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2019 16:22