Tamoxifen

Tamoxifen
Clinical data
Trade names	Nolvadex, Genox, Tamifen, others
Other names	TMX; ICI-46474
AHFS/Drugs.com	Monograph
MedlinePlus	a682414
License data	US DailyMed: Tamoxifen;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
Drug class	Selective estrogen receptor modulator
ATC code	L02BA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	~100%
Protein binding	>99% (albumin)
Metabolism	Liver (CYP3A4, CYP2C9, CYP2D6)
Metabolites	• N-Desmethyltamoxifen; • Endoxifen (4-hydroxy-N-desmethyltamoxifen); • Afimoxifene (4-hydroxytamoxifen); • N,N-Didesmethyltamoxifen; • Norendoxifen (4-hydroxy-N,N-didesmethyltamoxifen); • Others, conjugates
Elimination half-life	5–7 days
Excretion	Feces: 65%; Urine: 9%
Identifiers
	IUPAC name (Z)-2-[4-(1,2-Diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine;
CAS Number	10540-29-1 ; citrate: 54965-24-1;
PubChem CID	2733526; citrate: 2733525;
IUPHAR/BPS	1016;
DrugBank	DB00675 ; citrate: DBSALT000168;
ChemSpider	2015313 ; citrate: 2015312;
UNII	094ZI81Y45; citrate: 7FRV7310N6;
KEGG	D08559 ; citrate: D00966;
ChEBI	CHEBI:41774 ; citrate: CHEBI:9397;
ChEMBL	ChEMBL83 ; citrate: ChEMBL786;
PDB ligand	CTX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1034187 ;
ECHA InfoCard	100.031.004
Chemical and physical data
Formula	C26H29NO
Molar mass	371.524 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCOc1ccc(cc1)/C(c2ccccc2)=C(/CC)c3ccccc3;
	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- ; Key:NKANXQFJJICGDU-QPLCGJKRSA-N ;
	(verify)

Tamoxifen, sold under the brand name Nolvadex among others, is a selective estrogen receptor modulator used to prevent breast cancer in women and men. It is also being studied for other types of cancer. It has been used for Albright syndrome. Tamoxifen is typically taken daily by mouth for five years for breast cancer.

Serious side effects include a small increased risk of uterine cancer, stroke, vision problems, and pulmonary embolism. Common side effects include irregular periods, weight loss, and hot flashes. It may cause harm to the baby if taken during pregnancy or breastfeeding. It is a selective estrogen-receptor modulator (SERM) and works by decreasing the growth of breast cancer cells. It is a member of the triphenylethylene group of compounds.

Tamoxifen was initially made in 1962, by chemist Dora Richardson. It is on the World Health Organization's List of Essential Medicines. Tamoxifen is available as a generic medication. In 2020, it was the 317th most commonly prescribed medication in the United States, with more than 900 thousand prescriptions.

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