Methenmadinone acetate

Progestin
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
  • 805-84-5
PubChem CID
  • 188952
ChemSpider
  • 164183
UNII
  • KUR23M82TZ
CompTox Dashboard (EPA)
  • DTXSID701001282 Edit this at Wikidata
Chemical and physical data
FormulaC24H30O4
Molar mass382.500 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
  • 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

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]

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

References

  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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