Chemistry:Afimoxifene
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| Trade names | TamoGel |
| Other names | 4-Hydroxytamoxifen; 4-OHT; 4-HT; OHTAM; TamoGel |
| Routes of administration | Topical (gel) |
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| Formula | C26H29NO2 |
| Molar mass | 387.523 g·mol−1 |
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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]
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
- List of investigational sex-hormonal agents § Estrogenics
- List of selective estrogen receptor modulators
References
- ↑ 1.0 1.1 "Afimoxifene - BHR Pharma". AdisInsight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800019175.
- ↑ "Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6". The Journal of Pharmacology and Experimental Therapeutics 310 (3): 1062–1075. September 2004. doi:10.1124/jpet.104.065607. PMID 15159443.
- ↑ "Statement on a nonproprietary name adopted by the USAN council: Afimoxifene". American Medical Association. http://www.ama-assn.org/ama1/pub/upload/mm/365/afimoxifene.pdf.
- ↑ 4.0 4.1 "Mastalgia". Management of Breast Diseases. Springer. 16 November 2016. pp. 77–. ISBN 978-3-319-46356-8. https://books.google.com/books?id=f9iCDQAAQBAJ&pg=PA77.
- ↑ "A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women". Breast Cancer Research and Treatment 106 (3): 389–397. December 2007. doi:10.1007/s10549-007-9507-x. PMID 17351746.
- ↑ "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacological Reviews 67 (3): 505–540. July 2015. doi:10.1124/pr.114.009712. PMID 26023144.
- ↑ Hormones and Cancer: Breast and Prostate, An Issue of Endocrinology and Metabolism Clinics of North America. Elsevier Health Sciences. 3 October 2011. pp. 271–. ISBN 978-1-4557-1239-7. https://books.google.com/books?id=ZabQAQAAQBAJ&pg=PT271.
- ↑ "Anti-Androgenic Chemicals". Endocrine Disruptors in the Environment. Wiley. 23 May 2014. pp. 104–. ISBN 978-1-118-89115-5. https://books.google.com/books?id=s2ajAwAAQBAJ&pg=PT104.
- ↑ "Estrogen-related receptors as emerging targets in cancer and metabolic disorders". Current Topics in Medicinal Chemistry 6 (3): 203–215. 2006. doi:10.2174/1568026610606030203. PMID 16515477.
External links
- 4-hydroxytamoxifen at the US National Library of Medicine Medical Subject Headings (MeSH)
- Afimoxifene - AdisInsight
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