Afimoxifene

Afimoxifene

Names
IUPAC name (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol
Other names 4-hydroxytamoxifen
Identifiers
CAS Number	68392-35-8
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL489
ChemSpider	395987
ECHA InfoCard	100.155.464
KEGG	D06551
PubChem	449459
UNII	17197F0KYM
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 InChI=1/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-QPLCGJKRBX
SMILES CC\C(c1ccccc1)=C(c2ccc(OCCN(C)C)cc2)/c3ccc(O)cc3 O(c1ccc(cc1)/C(c2ccc(O)cc2)=C(\c3ccccc3)CC)CCN(C)C
Properties
Chemical formula	C26H29NO2
Molar mass	387.51396
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Afimoxifene,^[1] also known as 4-hydroxytamoxifen (4-OHT, 4-HT, OHTAM, others), is a selective estrogen receptor modulator and the active metabolite of tamoxifen.^[2]

Afimoxifene is the active ingredient in a transdermal gel formulation developed by Ascend Therapeutics, Inc. under the trademark TamoGel.^[1]

Afimoxifene has completed a phase II clinical trial for the treatment of cyclical mastalgia.^[3]

A study in France on 55 women showed that rubbing afimoxifene on the skin was as good as tamoxifen tablets at slowing breast cancer growth. A US trial will compare 6 weeks use before breast cancer surgery. Skin application can reduce systemic levels by a factor of nine and this is expected to reduce the unpleasant side-effects of tamoxifen.^[4]

References

1. "Statement on a nonproprietary name adopted by the USAN council: Afimoxifene" (PDF). American Medical Association. Retrieved 2008-03-26.
2. 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.
3. 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.
4. Hagan, Pat (6 Aug 2011). "Breast cancer gel shrinks tumours". Daily Mail. London.

External links

• 4-hydroxytamoxifen at the US National Library of Medicine Medical Subject Headings (MeSH)