Chemistry:Methenmadinone acetate

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Short description: Progestin


Methenmadinone acetate
Methenmadinone acetate.svg
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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC24H30O4
Molar mass382.500 g·mol−1
3D model (JSmol)

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. ↑ 1.0 1.1 Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. 1 November 2017. pp. 158–. ISBN 978-1-351-74347-1. https://books.google.com/books?id=GFM8DwAAQBAJ&pg=PT158. 
  2. ↑ Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. 6 December 2012. pp. 93,318. ISBN 978-94-009-8195-9. https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA93. 
  3. ↑ Chiral Drugs. Taylor & Francis. 23 October 2017. pp. 1127–. ISBN 978-1-351-80804-0. https://books.google.com/books?id=ZQA7DwAAQBAJ&pg=PT1127. 
  4. ↑ "Hormonal Treatment of Disorders of the Menstrual Cycle". Ovarian Function and its Disorders. Developments in Obstetrics and Gynecology. Springer. 1981. pp. 309–332. doi:10.1007/978-94-009-8195-9_11. ISBN 978-94-009-8197-3. 
  5. ↑ "Contraception". Pediatric and Adolescent Obstetrics and Gynecology. Springer Science & Business Media. 6 December 2012. pp. 236–. ISBN 978-1-4612-5064-7. https://books.google.com/books?id=l9XTBwAAQBAJ&pg=PA236. 
  6. ↑ 6.0 6.1 "Über neue Arzneimittel". Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. 8 March 2013. pp. 407–. ISBN 978-3-0348-7059-7. https://books.google.com/books?id=ZSH3BwAAQBAJ&pg=PA407. 
  7. ↑ "[Clinical Experience With the New Peroral Gestagen, 16-Methylene-6-Dehydro-17-Alpha-Acetoxyprogesterone (MDAP)]" (in de). Zentralblatt Fur Gynakologie 86: 1327–1332. September 1964. PMID 14324038. 
  8. ↑ "[Superlutin--a new Czechoslovak oral gestagen]" (in cs). Ceskoslovenska Gynekologie 30 (5): 351–355. June 1965. PMID 5835891. 
  9. ↑ "[Biological testing of methenmadinone acetate (Superlutin Spofa) in clinical trials]" (in cs). Ceskoslovenska Gynekologie 51 (9): 714–719. November 1986. PMID 3539369. 
  10. ↑ "[Superlutin]" (in cs). Ceskoslovenska Farmacie 15 (10): 543–544. December 1966. PMID 5980773. 
  11. ↑ "[Our experience in the treatment of menstruation disorders with Superlutin]" (in sk). Ceskoslovenska Gynekologie 31 (1): 86–88. February 1966. PMID 5932092. 
  12. ↑ "[3-Methylether-ethinylestradiol (Mestranol) and 6-dehydro-16-methylene-17-alpha-acetoxyprogesterone (Superlutin) in the therapy of functional bleedings]" (in de). Zentralblatt Fur Gynakologie 89 (28): 1030–1031. July 1967. PMID 5586402. 
  13. ↑ "[Some experiences with the effect of injectable progestational hormones]" (in Czech). Ceskoslovenska Gynekologie 34 (7): 407–9. September 1969. PMID 5809756. 
  14. ↑ "Steroid derivatives XXXIV. On the progestational activity of 6-dehydro-16-methylene-17α-acetoxyprogesterone". Steroids 4 (3): 415–42 1. 1964. doi:10.1016/0039-128X(64)90154-0. ISSN 0039-128X. 
  15. ↑ "[A Czechoslovak injection-contraceptive agent administered once a month]" (in de). Zentralblatt Fur Gynakologie 98 (3): 158–160. 1976. PMID 970015. 
  16. ↑ "Existing once-a-month combined injectable contraceptives". Contraception 49 (4): 293–301. April 1994. doi:10.1016/0010-7824(94)90029-9. PMID 8013216. 
  17. ↑ "Monthly Injectable Contraceptives". Long-Acting Contraception. 1983. pp. 93–103. OCLC 35018604. https://scholar.google.com/scholar?cluster=14664537528797672080. 
  18. ↑ "New biological application of contraceptive steroids.". Endocrinologia Experimentalis 2 (2): 101–110. 1968. https://www.popline.org/node/469522. 
  19. ↑ "[Biogest"] (in cs). Casopis Lekaru Ceskych 111 (30): 694–695. July 1972. PMID 5079918. https://www.popline.org/node/482986. Retrieved 2018-09-16. 
  20. ↑ 20.0 20.1 "[Towards a more physiological hormonal contraception"] (in de). Zentralblatt Fur Gynakologie 92 (10): 303–312. March 1970. PMID 4096927. https://www.popline.org/node/470458. Retrieved 2018-09-16. 
  21. ↑ "[Thyroid and ovarian hormones in ewes treated with gestagens and PMSG in the spring season"] (in sk). Veterinarni Medicina 40 (11): 345–352. November 1995. PMID 8659087. https://vetmed.vri.cz/?page=abstracts&detail=321. 
  22. ↑ "On the Way to a More Physiological Hormonal Contraception". Current Problems in Fertility. Springer. 1971. pp. 154–158. doi:10.1007/978-1-4615-8651-7_28. ISBN 978-1-4615-8653-1. https://www.popline.org/node/480951. Retrieved 2018-09-16. 



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