Methenmadinone caproate

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.

Not to be confused with Methenmadinone acetate.
Methenmadinone caproate
Clinical data
Other namesMMC; 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 classProgestogen; Progestin; Progestogen ester
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-16-methylene-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
CAS Number
UNII
Chemical and physical data
FormulaC28H38O4
Molar mass438.608 g·mol−1
3D model (JSmol)
  • O(C(CCCCC)=O)[C@@](C(C)=O)1C(=C)C[C@]([H])2[C@@]([H])3C=CC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
  • InChI=1S/C28H38O4/c1-6-7-8-9-25(31)32-28(19(3)29)18(2)16-24-22-11-10-20-17-21(30)12-14-26(20,4)23(22)13-15-27(24,28)5/h10-11,17,22-24H,2,6-9,12-16H2,1,3-5H3/t22-,23+,24+,26+,27+,28+/m1/s1
  • Key:WQBCIYORLVRAQX-BDPSOKNUSA-N

See also

References
  1. Syhora K, Mazáč R (1964). "Steroid derivatives. XXXI. A novel synthesis of 16-methylene-17α-acyloxy-20-ketopregnane derivatives". Collection of Czechoslovak Chemical Communications. 29 (10): 2351–2359. doi:10.1135/cccc19642351. ISSN 0010-0765.
  2. Stĕrba R (1976). "[A Czechoslovak injection-contraceptive agent administered once a month]". Zentralblatt Fur Gynakologie (in German). 98 (3): 158–160. PMID 970015.
  3. Toppozada MK (April 1994). "Existing once-a-month combined injectable contraceptives". Contraception. 49 (4): 293–301. doi:10.1016/0010-7824(94)90029-9. PMID 8013216.
  4. Toppozada MK (1983). "Monthly Injectable Contraceptives". In Goldsmith A, Toppozada M (eds.). Long-Acting Contraception. pp. 93–103. OCLC 35018604.
  5. Milne GW (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–. ISBN 978-1-351-74347-1.
  6. Milne GW (8 May 2018). Drugs: Synonyms and Properties: Synonyms and Properties. Taylor & Francis. pp. 1572–. ISBN 978-1-351-78989-9.
  7. Shapiro EL, Weber L, Harris H, Miskowicz C, Neri R, Herzog HL (July 1972). "Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17 -hydroxyprogesterones". Journal of Medicinal Chemistry. 15 (7): 716–720. doi:10.1021/jm00277a006. PMID 5043870.
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