Chlormethenmadinone acetate

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]

Chlormethenmadinone acetate
Clinical data
Trade namesBiogest, 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 classProgestogen; Progestin; Progestogen ester
Identifiers
IUPAC name
  • [(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
FormulaC24H29ClO4
Molar mass416.94 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

See also

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. 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)



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