methenmadinone caproate

{{Short description|Chemical compound}}

{{Distinguish|Methenmadinone acetate}}

{{Infobox drug

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| 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

| image = Methenmadinone caproate.svg

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| routes_of_administration = Intramuscular injection

| class = Progestogen; Progestin; Progestogen ester

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| CAS_number = 6723-94-0

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| UNII = T7YQK45FEA

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| synonyms = 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

| C=28 | H=38 | O=4

| 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

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| StdInChI = 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

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| StdInChIKey = WQBCIYORLVRAQX-BDPSOKNUSA-N

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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.{{cite journal| vauthors = Syhora K, Mazáč R |title=Steroid derivatives. XXXI. A novel synthesis of 16-methylene-17α-acyloxy-20-ketopregnane derivatives|journal=Collection of Czechoslovak Chemical Communications|volume=29|issue=10|year=1964|pages=2351–2359|issn=0010-0765|doi=10.1135/cccc19642351}}{{cite journal | vauthors = Stĕrba R | title = [A Czechoslovak injection-contraceptive agent administered once a month] | language = de | journal = Zentralblatt für Gynäkologie | volume = 98 | issue = 3 | pages = 158–160 | date = 1976 | pmid = 970015 }}{{cite journal | vauthors = Toppozada MK | title = Existing once-a-month combined injectable contraceptives | journal = Contraception | volume = 49 | issue = 4 | pages = 293–301 | date = April 1994 | pmid = 8013216 | doi = 10.1016/0010-7824(94)90029-9 }}{{cite book | vauthors = Toppozada MK | chapter = Monthly Injectable Contraceptives | pages = 93–103 | veditors = Goldsmith A, Toppozada M | title = Long-Acting Contraception | year = 1983 | oclc = 35018604 | url = https://scholar.google.com/scholar?cluster=14664537528797672080}} 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). MMC is the C17α caproate (hexanoate) ester of methenmadinone and an analogue of methenmadinone acetate (MMA; superlutin).{{cite book| vauthors = Milne GW |title=Ashgate Handbook of Endocrine Agents and Steroids|url=https://books.google.com/books?id=GFM8DwAAQBAJ&pg=PT158|date=1 November 2017|publisher=Taylor & Francis|isbn=978-1-351-74347-1|pages=158–}}{{cite book| vauthors = Milne GW |title=Drugs: Synonyms and Properties: Synonyms and Properties|url=https://books.google.com/books?id=xUlaDwAAQBAJ&pg=PT1572|date=8 May 2018|publisher=Taylor & Francis|isbn=978-1-351-78989-9|pages=1572–}}{{cite journal | vauthors = Shapiro EL, Weber L, Harris H, Miskowicz C, Neri R, Herzog HL | title = Synthesis and biological activity of 17-esters of 6-dehydro-16-methylene-17 -hydroxyprogesterones | journal = Journal of Medicinal Chemistry | volume = 15 | issue = 7 | pages = 716–720 | date = July 1972 | pmid = 5043870 | doi = 10.1021/jm00277a006 }} In addition to MMA, analogues of MMC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and megestrol caproate.