Afimoxifene

Afimoxifene
Clinical data
Trade names	TamoGel
Other names	4-Hydroxytamoxifen; 4-OHT; 4-HT; OHTAM
Routes of; administration	Topical (gel)
Identifiers
	IUPAC name (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol;
CAS Number	68392-35-8 ;
PubChem CID	449459;
ChemSpider	395987 ;
UNII	17197F0KYM;
KEGG	D06551 ;
ChEMBL	ChEMBL489 ;
CompTox Dashboard (EPA)	DTXSID7022384 ;
ECHA InfoCard	100.163.120
Chemical and physical data
Formula	C26H29NO2
Molar mass	387.5139 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC\C(c1ccccc1)=C(c2ccc(OCCN(C)C)cc2)/c3ccc(O)cc3;
	InChI InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25- ; Key:TXUZVZSFRXZGTL-QPLCGJKRSA-N ;
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Afimoxifene is a selective estrogen receptor modulator (SERM) of the triphenylethylene group and the major active metabolite of tamoxifen.^[1]^[2]^[3] The drug is under development under the tentative brand name TamoGel as a topical gel for the treatment of hyperplasia of the breast.^[1]^[4] It has completed a phase II clinical trial for cyclical mastalgia,^[5] but further studies are required before afimoxifene can be approved for this indication and marketed.^[4]

In addition to its antiestrogenic and estrogenic activity, afimoxifene has been found to act as an antagonist of the estrogen-related receptors (ERRs) ERRβ and ERRγ.^[6]^[7]

References[edit]

^ ^a ^b http://adisinsight.springer.com/drugs/800019175
^ Desta Z, Ward BA, Soukhova NV, Flockhart DA (2004). "Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6". J Pharmacol Exp Ther. 310 (3): 1062–1075. doi:10.1124/jpet.104.065607. PMID 15159443.
^ "Statement on a nonproprietary name adopted by the USAN council: Afimoxifene" (PDF). American Medical Association. Retrieved 2008-03-26.
^ ^a ^b Ismail Jatoi; Achim Rody (16 November 2016). Management of Breast Diseases. Springer. pp. 77–. ISBN 978-3-319-46356-8.
^ Mansel R, Goyal A, Nestour EL, Masini-Etévé V, O'Connell K (2007). "A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women". Breast Cancer Res. Treat. 106 (3): 389–397. doi:10.1007/s10549-007-9507-x. PMID 17351746.
^ Alice C. Levine (3 October 2011). Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America,. Elsevier Health Sciences. pp. 271–. ISBN 1-4557-1239-6.
^ Sushil K. Khetan (23 May 2014). Endocrine Disruptors in the Environment. Wiley. pp. 104–. ISBN 978-1-118-89115-5.

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