Methenmadinone caproate

Not to be confused with Methenmadinone acetate.

Methenmadinone caproate

Clinical data
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
Identifiers
IUPAC name [(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	6723-94-0  Y
UNII	T7YQK45FEA
Chemical and physical data
Formula	C28H38O4
Molar mass	438.608 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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

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. 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 für Gynäkologie (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.