Chlormethenmadinone acetate

Last updated
Chlormethenmadinone acetate
Chlormethenmadinone acetate.svg
Clinical data
Trade names Biogest, Sterolibrin, Antigest B, Agelin
Other namesSCH-12600; 6-Chloromethylene­dehydroacetoxy­progesterone; 17α-Acetoxy-6-chloro-16-methylene-6-dehydroprogesterone; 16-Methylene­chlormadinone acetate; 17α-Acetoxy-6-chloro-16-methylenepregna-4,6-diene-3,20-dione
Drug class Progestogen; Progestin; Progestogen ester
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-Acetyl-6-chloro-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
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H29ClO4
Molar mass 416.94 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=C(C4=CC(=O)CC[C@]34C)Cl)C)OC(=O)C
  • InChI=1S/C24H29ClO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-12,17-19H,1,6-10H2,2-5H3/t17-,18+,19+,22-,23+,24+/m1/s1
  • Key:MDTBKPVVPCIBIT-USYNNDFZSA-N

Chlormethenmadinone acetate (CMMA), also known as chlorsuperlutin, is a progestin medication which was developed in Czechoslovakia in the 1960s. [1] It has been used in combination with mestranol in birth control pills under the brand names Biogest, Sterolibrin, and Antigest B, [2] [3] and in veterinary medicine under the brand name Agelin. [4] Analogues of CMMA include bromethenmadinone acetate (bromsuperlutin), which was assessed but was never marketed, [3] [5] and melengestrol acetate (methylsuperlutin), which is used in veterinary medicine. [6]

See also

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Methenmadinone 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. 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. MMC is the C17α caproate (hexanoate) ester of methenmadinone and an analogue of methenmadinone acetate. In addition to MMA, analogues of MMC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and megestrol caproate.

<span class="mw-page-title-main">Bromethenmadinone acetate</span> Chemical compound

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References

  1. Sterba, R. (1968). New biological application of contraceptive steroids. Endocrinologia Experimentalis, 2(2), 101-110. https://www.popline.org/node/469522 Archived 2018-09-16 at the Wayback Machine
  2. Melich H (July 1972). "[Biogest]". Cas. Lek. Cesk. (in Czech). 111 (30): 694–5. PMID   5079918. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
  3. 1 2 Stĕrba R (March 1970). "[Towards a more physiological hormonal contraception]". Zentralbl Gynakol (in German). 92 (10): 303–12. PMID   4096927. Archived from the original on 2018-09-16. Retrieved 2018-09-16.
  4. 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]". Vet Med (Praha) (in Slovak). 40 (11): 345–52. PMID   8659087.
  5. Štěrba, R. (1971). "On the Way to a More Physiological Hormonal Contraception". Current Problems in Fertility. 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.
  6. R. G. Denkewalter; M. Tishler; G. Ehrhart; J. H. Biel, B. K. B. Lum, J. Büchi, C. A. Winter, K. Münzel, W. Kunz, E. J. Ariëns, F. Labhardt (8 March 2013). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN   978-3-0348-7059-7.{{cite book}}: CS1 maint: multiple names: authors list (link)