Methenmadinone caproate

Last updated
Methenmadinone caproate
Methenmadinone caproate.svg
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 class Progestogen; 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
Formula C28H38O4
Molar mass 438.608 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

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

Related Research Articles

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Hydroxyprogesterone caproate Medication

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<span class="mw-page-title-main">Segesterone acetate</span>

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Hydroxyprogesterone acetate Chemical compound

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Oxogestone phenpropionate

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Estradiol benzoate butyrate

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Levonorgestrel butanoate Chemical compound

Levonorgestrel butanoate (LNG-B), or levonorgestrel 17β-butanoate, is a steroidal progestin of the 19-nortestosterone group which was developed by the World Health Organization (WHO) in collaboration with the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development as a long-acting injectable contraceptive. It is the C17β butanoate ester of levonorgestrel, and acts as a prodrug of levonorgestrel in the body. The drug is at or beyond the phase III stage of clinical development, but has not been marketed at this time. It was first described in the literature, by the WHO, in 1983, and has been under investigation for potential clinical use since then.

Estradiol benzoate/progesterone Drug combination

Estradiol benzoate/progesterone (EB/P4), sold under the brand names Duogynon and Sistocyclin among others, is a combination medication of estradiol benzoate (EB), an estrogen, and progesterone (P4), a progestogen. It has been formulated both as short-acting oil solutions and long-acting microcrystalline aqueous suspensions and is given by injection into muscle either once or continuously at regular intervals.

Estradiol valerate/hydroxyprogesterone caproate

Estradiol valerate/hydroxyprogesterone caproate (EV/OHPC), sold under the brand names Gravibinon and Injectable No. 1 among others, is a combined estrogen and progestogen medication which is used in the treatment of threatened miscarriage and other indications and as a form of combined injectable birth control to prevent pregnancy. It contains estradiol valerate (EV), an estrogen, and hydroxyprogesterone caproate (OHPC), a progestin. The medication is given by injection into muscle once a day to once a month depending on the indication.

<span class="mw-page-title-main">Methenmadinone acetate</span> Progestin

Methenmadinone acetate (MMA), also known as methylenedehydroacetoxyprogesterone (MDAP) and sold under the brand names Superlutin and Antigest, is a progestin medication which was developed in Czechoslovakia in the 1960s. It is the C17α acetate ester of methenmadinone.

<span class="mw-page-title-main">Chlormadinone caproate</span> Chemical compound

Chlormadinone caproate (CMC) is a progestin and a progestogen ester which was studied for potential use in combined injectable contraceptives but was never marketed. It was assessed in combination with estradiol valerate at doses of 80 mg and 3 mg, respectively. In addition to chlormadinone acetate (CMA), analogues of CMC include gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, megestrol caproate, and methenmadinone caproate.

Lynestrenol phenylpropionate Chemical compound

Lynestrenol phenylpropionate (LPP), also known as ethynylestrenol phenylpropionate, is a progestin and a progestogen ester which was developed for potential use as a progestogen-only injectable contraceptive by Organon but was never marketed. It was assessed at doses of 25 to 75 mg in an oil solution once a month by intramuscular injection. LPP was associated with high contraceptive failure at the low dose and with poor cycle control. The medication was found to produce estrogenic effects in the endometrium in women due to transformation into estrogenic metabolites.

<span class="mw-page-title-main">Bromethenmadinone acetate</span> Chemical compound

Bromethenmadinone acetate is a progestin medication which was developed in Czechoslovakia and was described in 1970 but was never marketed. Analogues of BMMA include chlormethenmadinone acetate, melengestrol acetate, and methenmadinone acetate.

Estradiol valerate/methenmadinone caproate

Estradiol valerate/methenmadinone caproate (EV/MMC), known by the tentative brand name Lutofollin, is a combination medication of estradiol valerate (EV), an estrogen, and methenmadinone caproate, a progestin, which was developed for potential use as a once-a-month combined injectable contraceptive but was never marketed. It contained 10 mg EV and 60 mg MMC in 1 mL oil solution and was intended for administration by intramuscular injection once every 4 weeks.

References

  1. 1 2 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. 1 2 Stĕrba R (1976). "[A Czechoslovak injection-contraceptive agent administered once a month]". Zentralbl Gynakol (in German). 98 (3): 158–60. PMID   970015.
  3. 1 2 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. 1 2 Mokhtar K. Toppozada (1983). "Monthly Injectable Contraceptives". In Alfredo Goldsmith; Mokhtar Toppozada (eds.). Long-Acting Contraception. pp. 93–103. OCLC   35018604.
  5. G.W.A Milne (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–. ISBN   978-1-351-74347-1.
  6. George W.A Milne (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". J. Med. Chem. 15 (7): 716–20. doi:10.1021/jm00277a006. PMID   5043870.