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Methenmadinone caproate

December 18, 2023

Not to be confused with Methenmadinone acetate.

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.

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
  • 6723-94-0 Y
UNII
  • T7YQK45FEA
Chemical and physical data
FormulaC28H38O4
Molar mass438.608 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 edit

References edit

  1. ^ a b 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. ^ a b Stĕrba R (1976). "[A Czechoslovak injection-contraceptive agent administered once a month]". Zentralblatt Fur Gynakologie (in German). 98 (3): 158–160. PMID 970015.
  3. ^ a b 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. ^ a b 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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December 18, 2023
methenmadinone, caproate, confused, with, methenmadinone, acetate, also, known, superlutin, caproate, progestin, medication, which, developed, czechoslovakia, 1960s, studied, potential, combined, injectable, contraceptives, 1970s, never, marketed, studied, com. Not to be confused with Methenmadinone acetate 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 C17a 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 Methenmadinone caproateClinical dataOther namesMMC Superlutin caproate Methenmadinone hexanoate Lutofollin 17a Hydroxy 16 methyl 6 dehydroprogesterone caproate 17a Hydroxy 16 methylpregna 4 6 diene 3 20 dione 17a hexanoateRoutes ofadministrationIntramuscular injectionDrug classProgestogen Progestin Progestogen esterIdentifiersIUPAC 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 hexanoateCAS Number6723 94 0 YUNIIT7YQK45FEAChemical and physical dataFormulaC 28H 38O 4Molar mass438 608 g mol 13D model JSmol Interactive imageSMILES 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 OInChI 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 s1Key WQBCIYORLVRAQX BDPSOKNUSA NSee also editEstradiol valerate methenmadinone caproate List of progestogen esters Esters of 17a hydroxyprogesterone derivativesReferences edit a b Syhora K Mazac R 1964 Steroid derivatives XXXI A novel synthesis of 16 methylene 17a acyloxy 20 ketopregnane derivatives Collection of Czechoslovak Chemical Communications 29 10 2351 2359 doi 10 1135 cccc19642351 ISSN 0010 0765 a b Stĕrba R 1976 A Czechoslovak injection contraceptive agent administered once a month Zentralblatt Fur Gynakologie in German 98 3 158 160 PMID 970015 a b 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 a b Toppozada MK 1983 Monthly Injectable Contraceptives In Goldsmith A Toppozada M eds Long Acting Contraception pp 93 103 OCLC 35018604 Milne GW 1 November 2017 Ashgate Handbook of Endocrine Agents and Steroids Taylor amp Francis pp 158 ISBN 978 1 351 74347 1 Milne GW 8 May 2018 Drugs Synonyms and Properties Synonyms and Properties Taylor amp Francis pp 1572 ISBN 978 1 351 78989 9 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 nbsp This article about a steroid is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Methenmadinone caproate amp oldid 1168971928, wikipedia, wiki, book, books, library,

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