Enclomifene
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) | |
SMILES
| |
InChI
|
Enclomifene (INN) (former tentative brand names Androxal and EnCyzix), or enclomiphene (USAN), is a nonsteroidal selective estrogen receptor modulator of the triphenylethylene group which was under development for the treatment of male hypogonadism and type 2 diabetes.[1][2][3][4] By December 2016, it was in preregistration and was 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] In April 2021, development of enclomifene was discontinued for all indications.[3]
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[]
- ^ a b 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.
- ^ a b 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.
- ^ a b c "Enclomifene - Repros Therapeutics - AdisInsight".
- ^ a b c d e f Hill S, Arutchelvam V, Quinton R (2009). "Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in men". IDrugs. 12 (2): 109–19. PMID 19204885.
- ^ http://www.ema.europa.eu/en/medicines/human/EPAR/encyzix
External links[]
- Abandoned drugs
- Diethylamino compounds
- Organochlorides
- Phenol ethers
- Progonadotropins
- Selective estrogen receptor modulators
- Triphenylethylenes
- Genito-urinary system drug stubs