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.[1][2][3][4][5][6][7][8][9][10][11][12][13] It is the C17α acetate ester of methenmadinone.[1]
Quick Facts Clinical data, Trade names ...
Methenmadinone acetate |
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Trade names | Superlutin, Antigest |
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Other names | Superlutin; Superlutine; MMA; Methylenedehydroacetoxyprogesterone; MDAP; 17α-Hydroxy-16-methylene-δ6-progesterone 17α-acetate; 17α-Acetoxy-16-methylenepregna-4,6-diene-3,20-dione |
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Routes of administration | By mouth |
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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-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate
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Formula | C24H30O4 |
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Molar mass | 382.500 g·mol−1 |
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CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)CC[C@]34C)C)OC(=O)C
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InChI=1S/C24H30O4/c1-14-12-21-19-7-6-17-13-18(27)8-10-22(17,4)20(19)9-11-23(21,5)24(14,15(2)25)28-16(3)26/h6-7,13,19-21H,1,8-12H2,2-5H3/t19-,20+,21+,22+,23+,24+/m1/s1 Key:UXRDAJMOOGEIAQ-CKOZHMEPSA-N
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MMA given orally shows about 13-fold the progestogenic activity of parenteral progesterone in animal bioassays.[14]
Analogues of methenmadinone acetate include methenmadinone caproate (MMC), which was studied in combination with estradiol valerate as a combined injectable contraceptive (tentative brand name Lutofollin);[15][16][17] chlormethenmadinone acetate (chlorsuperlutin; SCH-12600; 6-chloro-MMA),[18] which has been used in combination with mestranol in birth control pills (brand names Biogest, Sterolibrin, Antigest B)[19][20] and in veterinary medicine (brand name Agelin);[21] bromethenmadinone acetate (bromsuperlutin; 6-bromo-MMA), which was assessed but was never marketed;[20][22] and melengestrol acetate (methylsuperlutin; 6-methyl-MMA), which is used in veterinary medicine.[6]
Greydanus DE (6 December 2012). "Contraception". In Lavery JP, Sanfilippo JS (eds.). Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. pp. 236–. ISBN 978-1-4612-5064-7.
Kunz W (8 March 2013). "Über neue Arzneimittel". In Denkewalter RG (ed.). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.
Hontela S (September 1964). "[Clinical Experience With the New Peroral Gestagen, 16-Methylene-6-Dehydro-17-Alpha-Acetoxyprogesterone (MDAP)]". Zentralblatt Fur Gynakologie (in German). 86: 1327–1332. PMID 14324038.
Králová A, Stĕrba R, Valová B (June 1965). "[Superlutin--a new Czechoslovak oral gestagen]". Ceskoslovenska Gynekologie (in Czech). 30 (5): 351–355. PMID 5835891.
Dvorák K, Presl J (November 1986). "[Biological testing of methenmadinone acetate (Superlutin Spofa) in clinical trials]". Ceskoslovenska Gynekologie (in Czech). 51 (9): 714–719. PMID 3539369.
Drázdil M (December 1966). "[Superlutin]". Ceskoslovenska Farmacie (in Czech). 15 (10): 543–544. PMID 5980773.
Horák C, Sedliak M (February 1966). "[Our experience in the treatment of menstruation disorders with Superlutin]". Ceskoslovenska Gynekologie (in Slovak). 31 (1): 86–88. PMID 5932092.
Stĕrba R (July 1967). "[3-Methylether-ethinylestradiol (Mestranol) and 6-dehydro-16-methylene-17-alpha-acetoxyprogesterone (Superlutin) in the therapy of functional bleedings]". Zentralblatt Fur Gynakologie (in German). 89 (28): 1030–1031. PMID 5586402.
Stĕrba R (September 1969). "[Some experiences with the effect of injectable progestational hormones]". Ceskoslovenska Gynekologie (in Czech). 34 (7): 407–9. PMID 5809756.
Čekan Z, Šeda M, Mikulášková J, Syhora K (1964). "Steroid derivatives XXXIV. On the progestational activity of 6-dehydro-16-methylene-17α-acetoxyprogesterone". Steroids. 4 (3): 415–42 1. doi:10.1016/0039-128X(64)90154-0. ISSN 0039-128X.
Stĕrba R (1976). "[A Czechoslovak injection-contraceptive agent administered once a month]". Zentralblatt Fur Gynakologie (in German). 98 (3): 158–160. PMID 970015.