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Identification
NameTamoxifen
Accession NumberDB00675  (APRD00123)
TypeSmall Molecule
GroupsApproved
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
Apo-tamox
Citofen
Crisafeno
Diemon
Gen-tamoxifen
Istubol
Noltam
Nourytam
Oncomox
Retaxim
Tamofen
Tamone
Tamoxasta
Tamoxifen
Tamoxifène
Tamoxifene
Tamoxifeno
Tamoxifenum
trans-Tamoxifen
Valodex
Zemide
External Identifiers
  • ICI-46474
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-tamoxifentablet20 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-tamoxifentablet10 mgoralDominion PharmacalNot applicableNot applicableCanada
Mylan-tamoxifentablet20 mgoralMylan Pharmaceuticals Ulc1994-12-31Not applicableCanada
Mylan-tamoxifentablet10 mgoralMylan Pharmaceuticals Ulc1994-12-31Not applicableCanada
Nolvadex Tab 10mgtablet10 mgoralAstrazeneca Canada Inc1994-12-312003-04-01Canada
Nolvadex-D Tab 20mgtablet20 mgoralAstrazeneca Canada Inc1995-12-31Not applicableCanada
Penta-tamoxifen Tabletstablet10 mgoralPentapharm Ltd.Not applicableNot applicableCanada
Penta-tamoxifen Tabletstablet20 mgoralPentapharm Ltd.Not applicableNot applicableCanada
PMS-tamoxifentablet10 mgoralPharmascience Inc1998-12-01Not applicableCanada
PMS-tamoxifentablet20 mgoralPharmascience Inc1998-12-01Not applicableCanada
Soltamoxliquid10 mg/5mLoralRosemont Pharmaceuticals Ltd2012-10-01Not applicableUs
Tamofen 10tablet10 mgoralSanofi Aventis Canada Inc1986-12-312011-01-11Canada
Tamofen 20tablet20 mgoralSanofi Aventis Canada Inc1986-12-312011-01-14Canada
Tamone - (10 Mg)tablet10 mgoralPfizer Canada Inc1996-12-312007-10-02Canada
Tamone - (20 Mg)tablet20 mgoralPfizer Canada Inc1996-12-312007-10-02Canada
Tamone Tab 10mgtablet10 mgoralAdria Laboratories Of Canada Ltd.1989-12-311996-09-10Canada
Tamone Tab 20mgtablet20 mgoralAdria Laboratories Of Canada Ltd.1989-12-311996-09-10Canada
Tamoplex Tab 10mgtablet10 mgoralDupont Merck Pharma Inc.1992-12-311996-09-09Canada
Tamoplex Tab 20mgtablet20 mgoralDupont Merck Pharma Inc.1992-12-311996-09-09Canada
Tamoxifentablet20 mgoralPharmel Inc1999-09-28Not applicableCanada
Tamoxifentablet10 mgoralPharmel Inc1999-09-28Not applicableCanada
Tamoxifene - 10tablet10 mgoralPro Doc Limitee2007-10-292011-07-27Canada
Tamoxifene - 20tablet20 mgoralPro Doc Limitee2007-10-292011-07-27Canada
Teva-tamoxifentablet20 mgoralTeva Canada Limited1990-12-31Not applicableCanada
Teva-tamoxifentablet10 mgoralTeva Canada Limited1990-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tamox Tab 10mgtablet10 mgoralApotex Inc1989-12-31Not applicableCanada
Apo-tamox Tab 20mgtablet20 mgoralApotex Inc1989-12-31Not applicableCanada
Tamoxifen Citratetablet, film coated10 mg/1oralA S Medication Solutions2003-02-20Not applicableUs
Tamoxifen Citratetablet, film coated20 mg/1oralTeva Pharmaceuticals USA Inc2003-02-21Not applicableUs
Tamoxifen Citratetablet20 mg/1oralWatson Laboratories, Inc.2011-08-15Not applicableUs
Tamoxifen Citratetablet20 mg/1oralAmerican Health Packaging2015-03-31Not applicableUs
Tamoxifen Citratetablet10 mg/1oralWatson Laboratories, Inc.2011-08-15Not applicableUs
Tamoxifen Citratetablet10 mg/1oralAmerican Health Packaging2015-03-31Not applicableUs
Tamoxifen Citratetablet20 mg/1oralMylan Pharmaceuticals Inc.2003-02-20Not applicableUs
Tamoxifen Citratetablet10 mg/1oralMc Kesson Packaging Services Business Unit Of Mc Kesson Corporation2007-09-14Not applicableUs
Tamoxifen Citratetablet10 mg/1oralMylan Pharmaceuticals Inc.2003-02-20Not applicableUs
Tamoxifen Citratetablet20 mg/1oralbryant ranch prepack2011-03-07Not applicableUs
Tamoxifen Citratetablet, film coated10 mg/1oralKAISER FOUNDATION HOSPITALS2008-03-24Not applicableUs
Tamoxifen Citratetablet, film coated20 mg/1oralPhysicians Total Care, Inc.2005-01-17Not applicableUs
Tamoxifen Citratetablet, film coated10 mg/1oralTeva Pharmaceuticals USA Inc2003-02-20Not applicableUs
Tamoxifen Citratetablet, film coated10 mg/1oralPhysicians Total Care, Inc.1994-04-26Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdifenMedicamerc
AdopanSawai Seiyaku
BilemTeva Int'l
CaditamCadila
CitofenNot Available
CrisafenoLKM
DoctamoxifeneDocpharma
EbefenEbewe
FenahexSandoz
GenoxMerck Serono
GynatamBiogalenic
IstubalAstraZeneca
MammonexCP Pharmaceuticals
NeophedanAspen Pharmacare
NoltamNot Available
NolvadexAstraZeneca
Nolvadex-DAstraZeneca
NovofenRemedica
OncomoxSun
TadexOrion
TamifenMedochemie
TamizamMithra
TamofenSanofi-Aventis
TamoneprinActavis
TamoplexPharmachemie
TamoxenAscent
TamoxilonCelon
TamteroHetero
TecnotaxZodiac
TomifenAlkem
ValodexNot Available
ZemideNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Tamoxifen Citrate
54965-24-1
Thumb
  • InChI Key: FQZYTYWMLGAPFJ-OQKDUQJOSA-N
  • Monoisotopic Mass: 563.251917165
  • Average Mass: 563.6381
DBSALT000168
Categories
UNII094ZI81Y45
CAS number10540-29-1
WeightAverage: 371.5146
Monoisotopic: 371.224914555
Chemical FormulaC26H29NO
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenylpropene
  • Phenylpropane
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationTamoxifen is indicated for the treatment of metastatic breast cancer in women and men and ductal carcinoma in Situ.
PharmacodynamicsTamoxifen 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 actionTamoxifen 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.
Related Articles
AbsorptionWhen 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 distributionNot Available
Protein bindingNot 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.

SubstrateEnzymesProduct
Tamoxifen
N-DesmethyltamoxifenDetails
Tamoxifen
4-HydroxytamoxifenDetails
Tamoxifen
3-Hydroxytamoxifen (Droloxifene)Details
Tamoxifen
Tamoxifen N-oxideDetails
Tamoxifen
Alpha-hydroxytamoxifenDetails
Tamoxifen
Tamoxifen-N-glucuronideDetails
4-Hydroxytamoxifen
EndoxifenDetails
Alpha-hydroxytamoxifen
Not Available
Alpha-hydroxy-tamoxifen-O-glucuronideDetails
4-Hydroxytamoxifen
4-hydroxytamoxifen sulfateDetails
4-Hydroxytamoxifen
4-hydroxytamoxifen-N-glucuronideDetails
4-Hydroxytamoxifen
4-hydroxytamoxifen-O-glucuronideDetails
N-Desmethyltamoxifen
alpha-Hydroxy-N-desmethyltamoxifenDetails
N-Desmethyltamoxifen
EndoxifenDetails
Endoxifen
Endoxifen sulfateDetails
Endoxifen
Not Available
NorendoxifenDetails
Endoxifen
Endoxifen O-glucuronideDetails
N-Desmethyltamoxifen
N-Didesmethyl-tamoxifenDetails
4-Hydroxytamoxifen
3,4-Dihydroxy-tamoxifenDetails
Tamoxifen
4'-HydroxytamoxifenDetails
4-Hydroxytamoxifen
cis-4-HydroxytamoxifenDetails
Tamoxifen N-oxide
alpha-Hydroxytamoxifen N-oxideDetails
Alpha-hydroxytamoxifen
alpha-Hydroxytamoxifen N-oxideDetails
Alpha-hydroxytamoxifen
Not Available
alpha-Hydroxy-N-desmethyltamoxifenDetails
Route of elimination65% 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 lifeThe 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.

ToxicitySigns observed at the highest doses following studies to determine LD50 in animals were respiratory difficulties and convulsions.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Tamoxifen Metabolism PathwayDrug metabolismSMP00606
Tamoxifen Action PathwayDrug actionSMP00471
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2D6
Gene symbol: CYP2D6
UniProt: P10635
rs3892097 CYP2D6*4A Allele, homozygotePoor response to drug treatment, shorter time to relapse17115111
SNP Mediated Adverse Drug Reactions
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeAdverse ReactionReference(s)
Coagulation factor V
Gene symbol: F5
UniProt: P12259
rs6025 Not AvailableA alleleBreast cancer patients taking tamoxifen as part of treatment regimine are more likely to experience a thromboembolic event.20554945
ADMET
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 )
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
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)
US6127425 No1998-06-262018-06-26Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point97 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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
ATC CodesL02BA01
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (102 KB)
MSDSDownload (74.8 KB)
Interactions
Drug Interactions
Drug
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.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Tamoxifen.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Tamoxifen.
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.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Tamoxifen.
AnastrozoleThe serum concentration of Anastrozole can be decreased when it is combined with Tamoxifen.
BexaroteneThe serum concentration of Tamoxifen can be decreased when it is combined with Bexarotene.
BosentanThe serum concentration of Tamoxifen can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Tamoxifen.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Tamoxifen.
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.
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.
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.
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.
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.
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.
CitalopramTamoxifen may increase the QTc-prolonging activities of Citalopram.
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.
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.
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.
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.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Tamoxifen.
ConivaptanThe serum concentration of Tamoxifen can be increased when it is combined with Conivaptan.
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Tamoxifen.
DabrafenibThe serum concentration of Tamoxifen can be decreased when it is combined with Dabrafenib.
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.
DasatinibThe serum concentration of Tamoxifen can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Tamoxifen can be decreased when it is combined with Deferasirox.
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.
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.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Tamoxifen.
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.
DofetilideTamoxifen may increase the QTc-prolonging activities of Dofetilide.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Tamoxifen.
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.
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.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Tamoxifen.
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.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Tamoxifen.
FloxuridineThe metabolism of Tamoxifen can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Tamoxifen can be decreased when combined with Fluconazole.
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.
FosaprepitantThe serum concentration of Tamoxifen can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Tamoxifen can be increased when it is combined with Fusidic Acid.
GoserelinTamoxifen may increase the QTc-prolonging activities of Goserelin.
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.
IdelalisibThe serum concentration of Tamoxifen can be increased when it is combined with Idelalisib.
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.
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.
IvacaftorThe serum concentration of Tamoxifen can be increased when it is combined with Ivacaftor.
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.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Tamoxifen.
LetrozoleThe serum concentration of Letrozole can be decreased when it is combined with Tamoxifen.
LeuprolideTamoxifen may increase the QTc-prolonging activities of Leuprolide.
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.
LuliconazoleThe serum concentration of Tamoxifen can be increased when it is combined with Luliconazole.
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.
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.
MifepristoneThe serum concentration of Tamoxifen can be increased when it is combined with Mifepristone.
MipomersenTamoxifen may increase the hepatotoxic activities of Mipomersen.
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.
MitotaneThe serum concentration of Tamoxifen can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Tamoxifen.
NelfinavirThe metabolism of Tamoxifen can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Tamoxifen can be increased when it is combined with Netupitant.
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.
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.
OspemifeneThe risk or severity of adverse effects can be increased when Tamoxifen is combined with Ospemifene.
PalbociclibThe serum concentration of Tamoxifen can be increased when it is combined with Palbociclib.
PanobinostatThe serum concentration of Tamoxifen can be increased when it is combined with Panobinostat.
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.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Tamoxifen.
Peginterferon alfa-2bThe serum concentration of Tamoxifen can be decreased when it is combined with Peginterferon alfa-2b.
PhenytoinThe metabolism of Tamoxifen can be increased when combined with Phenytoin.
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.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Tamoxifen.
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.
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.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Tamoxifen.
RifabutinThe metabolism of Tamoxifen can be increased when combined with Rifabutin.
RifampicinThe metabolism of Tamoxifen can be increased when combined with Rifampicin.
RifapentineThe metabolism of Tamoxifen can be increased when combined with Rifapentine.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Tamoxifen.
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.
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.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Tamoxifen.
SecobarbitalThe metabolism of Tamoxifen can be increased when combined with Secobarbital.
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.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Tamoxifen.
SiltuximabThe serum concentration of Tamoxifen can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Tamoxifen can be increased when it is combined with Simeprevir.
St. John's WortThe serum concentration of Tamoxifen can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Stiripentol resulting in a loss in efficacy.
SulfisoxazoleThe metabolism of Tamoxifen can be decreased when combined with Sulfisoxazole.
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.
ThioridazineThe serum concentration of the active metabolites of Tamoxifen can be reduced when Tamoxifen is used in combination with Thioridazine resulting in a loss in efficacy.
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.
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.
TocilizumabThe serum concentration of Tamoxifen can be decreased when it is combined with Tocilizumab.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Tamoxifen.
TorasemideThe metabolism of Torasemide can be decreased when combined with Tamoxifen.
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.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Tamoxifen.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Tamoxifen.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Tamoxifen.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonistagonist
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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonistagonist
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 manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by...
Gene Name:
ESR2
Uniprot ID:
Q92731
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
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, differentiation, migration and adhesion, tumorigenesis, cardiac hypertrophy, angiogenesis, platelet function and inflammation, by directly phosphorylating targets such as RAF1, BCL2, CSPG4, TNNT2/CTNT, or activating signaling cascade involving MAPK1/3 (ERK1/2) and RAP1GAP. Involved in cell proliferation and cell growth arrest by positive and negative regulation of the cell cycle. Can promote cell growth by phosphorylating and activating RAF1, which mediates the activation of the MAPK/ERK signaling cascade, and/or by up-regulating CDKN1A, which facilitates active cyclin-dependent kinase (CDK) complex formation in glioma cells. In intestinal cells stimulated by the phorbol ester PMA, can trigger a cell cycle arrest program which is associated with the accumulation of the hyper-phosphorylated growth-suppressive form of RB1 and induction of the CDK inhibitors CDKN1A and CDKN1B. Exhibits anti-apoptotic function in glioma cells and protects them from apoptosis by suppressing the p53/TP53-mediated activation of IGFBP3, and in leukemia cells mediates anti-apoptotic action by phosphorylating BCL2. During macrophage differentiation induced by macrophage colony-stimulating factor (CSF1), is translocated to the nucleus and is associated with macrophage development. After wounding, translocates from focal contacts to lamellipodia and participates in the modulation of desmosomal adhesion. Plays a role in cell motility by phosphorylating CSPG4, which induces association of CSPG4 with extensive lamellipodia at the cell periphery and polarization of the cell accompanied by increases in cell motility. Is highly expressed in a number of cancer cells where it can act as a tumor promoter and is implicated in malignant phenotypes of several tumors such as gliomas and breast cancers. Negatively regulates myocardial contractility and positively regulates angiogenesis, platelet aggregation and thrombus formation in arteries. Mediates hypertrophic growth of neonatal cardiomyocytes, in part through a MAPK1/3 (ERK1/2)-dependent signaling pathway, and upon PMA treatment, is required to induce cardiomyocyte hypertrophy up to heart failure and death, by increasing protein synthesis, protein-DNA ratio and cell surface area. Regulates cardiomyocyte function by phosphorylating cardiac troponin T (TNNT2/CTNT), which induces significant reduction in actomyosin ATPase activity, myofilament calcium sensitivity and myocardial contractility. In angiogenesis, is required for full endothelial cell migration, adhesion to vitronectin (VTN), and vascular endothelial growth factor A (VEGFA)-dependent regulation of kinase activation and vascular tube formation. Involved in the stabilization of VEGFA mRNA at post-transcriptional level and mediates VEGFA-induced cell proliferation. In the regulation of calcium-induced platelet aggregation, mediates signals from the CD36/GP4 receptor for granule release, and activates the integrin heterodimer ITGA2B-ITGB3 through the RAP1GAP pathway for adhesion. During response to lipopolysaccharides (LPS), may regulate selective LPS-induced macrophage functions involved in host defense and inflammation. But in some inflammatory responses, may negatively regulate NF-kappa-B-induced genes, through IL1A-dependent induction of NF-kappa-B inhibitor alpha (NFKBIA/IKBA). Upon stimulation with 12-O-tetradecanoylphorbol-13-acetate (TPA), phosphorylates EIF4G1, which modulates EIF4G1 binding to MKNK1 and may be involved in the regulation of EIF4E phosphorylation. Phosphorylates KIT, leading to inhibition of KIT activity. Phosphorylates ATF2 which promotes cooperation between ATF2 and JUN, activating transcription.
Components:
NameUniProt IDDetails
Protein kinase C alpha typeP17252 Details
Protein kinase C beta typeP05771 Details
Protein kinase C delta typeQ05655 Details
Protein kinase C epsilon typeQ02156 Details
Protein kinase C gamma typeP05129 Details
Protein kinase C iota typeP41743 Details
Protein kinase C theta typeQ04759 Details
Protein kinase C zeta typeQ05513 Details
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. Kuderer NM, Peppercorn J: CYP2D6 testing in breast cancer: ready for prime time? Oncology (Williston Park). 2009 Dec;23(14):1223-32. [PubMed:20120834 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]
  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 ]
  4. 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 ]
  5. 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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. 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]
  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. 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
substrateinhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]
  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. 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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:
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular Weight:
60845.33 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  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:
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
Molecular Weight:
60310.285 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds (PubMed:9224773).
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular Weight:
60032.975 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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 acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
Gene Name:
CES1
Uniprot ID:
P23141
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
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. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
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 or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
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 homodimerization activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1 (By similarity).
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular Weight:
60024.535 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 estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so ...
Gene Name:
SULT1A1
Uniprot ID:
P50225
Molecular Weight:
34165.13 Da
References
  1. Hertz DL, McLeod HL, Irvin WJ Jr: Tamoxifen and CYP2D6: a contradiction of data. Oncologist. 2012;17(5):620-30. doi: 10.1634/theoncologist.2011-0418. Epub 2012 Apr 24. [PubMed:22531359 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
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
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. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
  3. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372 ]
  4. 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 ]
  5. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
  6. Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675 ]
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
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
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on July 27, 2016 01:56