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. The drug is under development under the tentative brand name TamoGel as a topical gel for the treatment of hyperplasia of the breast. It has completed a phase II clinical trial for cyclical mastalgia, but further studies are required before afimoxifene can be approved for this indication and marketed.

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). 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.

References