Wikipedia

Methenmadinone acetate

This article is about the medication. For other uses, see MDAP (disambiguation).

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]

Methenmadinone acetate
Clinical data
Trade namesSuperlutin, Antigest
Other namesSuperlutin; Superlutine; MMA; Methylene­dehydroacetoxy­progesterone; MDAP; 17α-Hydroxy-16-methylene-δ6-progesterone 17α-acetate; 17α-Acetoxy-16-methylenepregna-4,6-diene-3,20-dione
Routes of
administration		By mouth
Drug classProgestogen; Progestin; Progestogen ester
Identifiers
  • [(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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H30O4
Molar mass382.500 g·mol−1
3D model (JSmol)
  • 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
  • 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

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]

See also

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References

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  1. ^ a b Milne GW (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–. ISBN 978-1-351-74347-1.
  2. ^ Horsky J, Presl J (6 December 2012). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 93, 318. ISBN 978-94-009-8195-9.
  3. ^ Challener CA (23 October 2017). Chiral Drugs. Taylor & Francis. pp. 1127–. ISBN 978-1-351-80804-0.
  4. ^ Horský J, Presl J (1981). "Hormonal Treatment of Disorders of the Menstrual Cycle". Ovarian Function and its Disorders. Developments in Obstetrics and Gynecology. Springer. pp. 309–332. doi:10.1007/978-94-009-8195-9_11. ISBN 978-94-009-8197-3.
  5. ^ 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.
  6. ^ a b 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.
  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.
  8. ^ Králová A, Stĕrba R, Valová B (June 1965). "[Superlutin--a new Czechoslovak oral gestagen]". Ceskoslovenska Gynekologie (in Czech). 30 (5): 351–355. PMID 5835891.
  9. ^ 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.
  10. ^ Drázdil M (December 1966). "[Superlutin]". Ceskoslovenska Farmacie (in Czech). 15 (10): 543–544. PMID 5980773.
  11. ^ 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.
  12. ^ 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.
  13. ^ Stĕrba R (September 1969). "[Some experiences with the effect of injectable progestational hormones]". Ceskoslovenska Gynekologie (in Czech). 34 (7): 407–9. PMID 5809756.
  14. ^ 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.
  15. ^ Stĕrba R (1976). "[A Czechoslovak injection-contraceptive agent administered once a month]". Zentralblatt Fur Gynakologie (in German). 98 (3): 158–160. PMID 970015.
  16. ^ 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.
  17. ^ Toppozada MK (1983). "Monthly Injectable Contraceptives". In Goldsmith A, Toppozada M (eds.). Long-Acting Contraception. pp. 93–103. OCLC 35018604.
  18. ^ Sterba R (1968). "New biological application of contraceptive steroids". Endocrinologia Experimentalis. 2 (2): 101–110. Archived from the original on 2018-09-16.
  19. ^ Melich H (July 1972). "[Biogest]". Casopis Lekaru Ceskych (in Czech). 111 (30): 694–695. PMID 5079918. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
  20. ^ a b Stĕrba R (March 1970). "[Towards a more physiological hormonal contraception]". Zentralblatt Fur Gynakologie (in German). 92 (10): 303–312. PMID 4096927. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
  21. ^ Bekeová E, Krajnicáková M, Hendrichovský V, Maracek I (November 1995). "[Thyroid and ovarian hormones in ewes treated with gestagens and PMSG in the spring season]". Veterinarni Medicina (in Slovak). 40 (11): 345–352. PMID 8659087. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
  22. ^ Štěrba R (1971). "On the Way to a More Physiological Hormonal Contraception". Current Problems in Fertility. Springer. pp. 154–158. doi:10.1007/978-1-4615-8651-7_28. ISBN 978-1-4615-8653-1. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
 

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