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Chemical compound
Chlormethenmadinone acetate
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
[(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 )
Formula C 24 H 29 Cl O 4
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
References
^ 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 .
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )