From Wikipedia, the free encyclopedia
Chemical compound
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 |
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Routes of administration |
Intramuscular injection |
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Drug class |
Progestogen;
Progestin;
Progestogen ester |
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[(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
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CAS Number | |
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UNII | |
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Formula | C28H38O4 |
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Molar mass | 438.608 g·mol−1 |
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3D model (
JSmol) | |
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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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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
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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
References
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PRTooltip Progesterone receptor | Agonists |
- Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
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6,6-Difluoronorethisterone acetate
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17α-Allyl-19-nortestosterone
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Allylestrenol
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Altrenogest
-
Chloroethynylnorgestrel
-
Cingestol
-
Danazol
-
Desogestrel
-
Dienogest
-
Ethinylandrostenediol
-
Ethisterone
-
Ethynerone
-
Etonogestrel
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Etynodiol
-
Etynodiol diacetate
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Gestodene
-
Gestrinone
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Levonorgestrel
-
Levonorgestrel esters (e.g.,
levonorgestrel butanoate)
-
Lynestrenol
-
Lynestrenol phenylpropionate
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Metynodiol
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Metynodiol diacetate
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Norelgestromin
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Norethisterone (norethindrone)
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Norethisterone esters (e.g.,
norethisterone acetate,
norethisterone enanthate)
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Noretynodrel
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Norgesterone
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Norgestimate
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Norgestrel
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Norgestrienone
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Norvinisterone
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Oxendolone
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Quingestanol
-
Quingestanol acetate
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Tibolone
-
Tigestol
-
Tosagestin; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
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11β-Methyl-19-nortestosterone dodecylcarbonate
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19-Nor-5-androstenediol
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19-Nor-5-androstenedione
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19-Nordehydroepiandrosterone
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Bolandiol
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Bolandiol dipropionate
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Bolandione
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Dimethisterone
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Dienedione
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Dienolone
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Dimethandrolone
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Dimethandrolone buciclate
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Dimethandrolone dodecylcarbonate
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Dimethandrolone undecanoate
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Dimethyldienolone
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Dimethyltrienolone
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Ethyldienolone
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Ethylestrenol (ethylnandrol)
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Methyldienolone
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Metribolone (R-1881)
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Methoxydienone (methoxygonadiene)
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Mibolerone
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Nandrolone
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Nandrolone esters (e.g.,
nandrolone decanoate,
nandrolone phenylpropionate)
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Norethandrolone
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Normethandrone (methylestrenolone, normethandrolone, normethisterone)
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RU-2309
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Tetrahydrogestrinone
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Trenbolone (trienolone)
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Trenbolone esters (e.g.,
trenbolone acetate,
trenbolone enanthate)
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Trendione
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Trestolone
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Trestolone acetate
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Mixed (
SPRMsTooltip Selective progesterone receptor modulators) | |
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Antagonists | |
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mPRTooltip Membrane progesterone receptor (
PAQRTooltip Progestin and adipoQ receptor) | |
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