Chemistry:Methenmadinone caproate
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| Other names | MMC; Superlutin caproate; Methenmadinone hexanoate; Lutofollin; 17α-Hydroxy-16-methyl-6-dehydroprogesterone caproate; 17α-Hydroxy-16-methylpregna-4,6-diene-3,20-dione 17α-hexanoate |
| Routes of administration | Intramuscular injection |
| Drug class | Progestogen; Progestin; Progestogen ester |
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| Chemical and physical data | |
| Formula | C28H38O4 |
| Molar mass | 438.608 g·mol−1 |
| 3D model (JSmol) | |
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Methenmadinone caproate (MMC, also known as superlutin caproate) is a progestin medication which was developed in Czechoslovakia in the 1960s and was studied for potential use in combined injectable contraceptives in the 1970s but was never marketed.[1][2][3][4] It was studied as a combined injectable contraceptive in combination with estradiol valerate at doses of 60 mg and 10 mg, respectively, once a month by intramuscular injection (tentative brand name Lutofollin).[2][3][4] MMC is the C17α caproate (hexanoate) ester of methenmadinone and an analogue of methenmadinone acetate (MMA; superlutin).[5][6][1][7] In addition to MMA, analogues of MMC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and megestrol caproate.
See also
- Estradiol valerate/methenmadinone caproate
- List of progestogen esters § Esters of 17α-hydroxyprogesterone derivatives
References
- ↑ 1.0 1.1 "Steroid derivatives. XXXI. A novel synthesis of 16-methylene-17α-acyloxy-20-ketopregnane derivatives". Collection of Czechoslovak Chemical Communications 29 (10): 2351–2359. 1964. doi:10.1135/cccc19642351. ISSN 0010-0765.
- ↑ 2.0 2.1 "[A Czechoslovak injection-contraceptive agent administered once a month]" (in de). Zentralblatt Fur Gynakologie 98 (3): 158–160. 1976. PMID 970015.
- ↑ 3.0 3.1 "Existing once-a-month combined injectable contraceptives". Contraception 49 (4): 293–301. April 1994. doi:10.1016/0010-7824(94)90029-9. PMID 8013216.
- ↑ 4.0 4.1 "Monthly Injectable Contraceptives". Long-Acting Contraception. 1983. pp. 93–103. OCLC 35018604. https://scholar.google.com/scholar?cluster=14664537528797672080.
- ↑ Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. 1 November 2017. pp. 158–. ISBN 978-1-351-74347-1. https://books.google.com/books?id=GFM8DwAAQBAJ&pg=PT158.
- ↑ Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. 8 May 2018. pp. 1572–. ISBN 978-1-351-78989-9. https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT1572.
- ↑ "Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17 -hydroxyprogesterones". Journal of Medicinal Chemistry 15 (7): 716–720. July 1972. doi:10.1021/jm00277a006. PMID 5043870.
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