Chlormethenmadinone acetate

Chlormethenmadinone acetate
Clinical data
Trade names	Biogest, Sterolibrin, Antigest B, Agelin
Other names	SCH-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
	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	6799-23-1;
PubChem CID	175513;
ChemSpider	152916;
ChEMBL	ChEMBL3276150;
CompTox Dashboard (EPA)	DTXSID00987408 ;
Chemical and physical data
Formula	C24H29ClO4
Molar mass	416.94 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

^ Sterba R (1968). "New biological application of contraceptive steroids". Endocrinologia Experimentalis. 2 (2): 101–110. Archived from the original on 16 September 2018.
^ 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.
^ ^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.
^ 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.
^ 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.
^ von Kunz W (8 March 2013). "Über neue Arzneimittel". In Denkewalter RG, Tishler M, Ehrhart G, Biel JH, Lum BK, Büchi J, Winter CA, Münzel K, Kunz W, Ariëns EJ, Labhardt F (eds.). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.

[Sterba1968-1] Sterba R (1968). "New biological application of contraceptive steroids". Endocrinologia Experimentalis. 2 (2): 101–110. Archived from the original on 16 September 2018.

[pmid5079918-2] 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.

[pmid4096927-3] 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.

[pmid8659087-4] 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]". Veterinarni Medicina (in Slovak). 40 (11): 345–352. PMID 8659087. Archived from the original on 2018-09-16. Retrieved 2018-09-16.

[Štěrba1971-5] 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.

[DenkewalterTishler2013-6] von Kunz W (8 March 2013). "Über neue Arzneimittel". In Denkewalter RG, Tishler M, Ehrhart G, Biel JH, Lum BK, Büchi J, Winter CA, Münzel K, Kunz W, Ariëns EJ, Labhardt F (eds.). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.

[1]

[2]

[3]

[4]

[5]

[6]