Enclomifene
Enclomifene (INN) (tentative brand names Androxal and EnCyzix), or enclomiphene (USAN), is a nonsteroidal selective estrogen receptor modulator (SERM) of the triphenylethylene group that is under development for the treatment of male hypogonadism.[1][2][3][4] As of December 2016, it is in the pre-registration phase of development and is under review by the Food and Drug Administration in the United States and the European Medicines Agency in the European Union.[3] In January 2018, the Committee for Medicinal Products for Human Use of the European Medicines Agency recommended refusal of marketing authorization for enclomifene for the treatment of secondary hypogonadism.[5]
 | |
| Clinical data | |
|---|---|
| Trade names | Androxal |
| Other names | Enclomiphene; (E)-Clomifene; RMI-16289; Enclomid; Enclomifene citrate; Enclomiphene citrate |
| Routes of administration | By mouth |
| Drug class | Selective estrogen receptor modulator; Progonadotropin |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C26H28ClNO |
| Molar mass | 405.97 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
Enclomifene acts by antagonizing the estrogen receptor (ER) in the pituitary gland, which reduces negative feedback by estrogen on the hypothalamic-pituitary-gonadal axis, thereby increasing gonadotropin secretion and hence gonadal production of testosterone.[4] It is one of the two stereoisomers of clomifene, which itself is a mixture of 38% zuclomifene and 62% enclomifene.[4] Enclomifene is the (E)-stereoisomer of clomifene, while zuclomifene is the (Z)-stereoisomer.[1][2] Whereas zuclomifene is more estrogenic, enclomifene is more antiestrogenic.[4] In accordance, unlike enclomifene, zuclomifene is antigonadotropic due to activation of the ER and reduces testosterone levels in men.[4] As such, isomerically pure enclomifene is more favorable than clomifene as a progonadotropin for the treatment of male hypogonadism.[4]
References
- J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 298–. ISBN 978-1-4757-2085-3.
- I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 79–. ISBN 978-0-7514-0499-9.
- http://adisinsight.springer.com/drugs/800019625
- Hill S, Arutchelvam V, Quinton R (2009). "Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men" (PDF). IDrugs. 12 (2): 109–19. PMID 19204885.
- http://www.ema.europa.eu/en/medicines/human/EPAR/encyzix