Afimoxifene

Afimoxifene
Clinical data
Trade names	TamoGel
Other names	4-Hydroxytamoxifen; 4-OHT; 4-HT; OHTAM; TamoGel
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 ;
ChEBI	CHEBI:44616;
ChEMBL	ChEMBL489 ;
CompTox Dashboard (EPA)	DTXSID7022384 ;
ECHA InfoCard	100.163.120
Chemical and physical data
Formula	C26H29NO2
Molar mass	387.523 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 ;
	(verify)

Afimoxifene, also known as 4-hydroxytamoxifen (4-OHT) and by its tentative brand name TamoGel, is a selective estrogen receptor modulator (SERM) of the triphenylethylene group and an 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]

Quick facts Clinical data, Trade names ...

Afimoxifene is a SERM and hence acts as a tissue-selective agonist–antagonist of the estrogen receptors ERα and ERβ with mixed estrogenic and antiestrogenic activity depending on the tissue. It is also an agonist of the G protein-coupled estrogen receptor (GPER) with relatively low affinity (100–1,000 nM, relative to 3–6 nM for estradiol).^[6] In addition to its estrogenic and antiestrogenic activity, afimoxifene has been found to act as an antagonist of the estrogen-related receptors (ERRs) ERRβ and ERRγ.^[7]^[8]^[9]

See also