Chlormadinone acetate

Chlormadinone acetate
Clinical data

Routes of administration	By mouth
ATC code	G03DB06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Biological half-life	34–38 hours
Identifiers
IUPAC name 17-(Acetyloxy)-6-chloropregna-4,6-diene-3,20-dione
CAS Number	302-22-7
PubChem CID	9324
ChemSpider	8963
KEGG	D01299
ChEBI	CHEBI:31394
ChEMBL	CHEMBL110691
ECHA InfoCard	100.005.563
Chemical and physical data
Formula	C₂₃H₂₉ClO₄
Molar mass	404.92696 g/mol
3D model (Jmol)	Interactive image
SMILES CC(=O)[C@]1(CC[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/C23H29ClO4/c1-13(25)23(28-14(2)26)10-7-18-16-12-20(24)19-11-15(27)5-8-21(19,3)17(16)6-9-22(18,23)4/h11-12,16-18H,5-10H2,1-4H3/t16-,17+,18+,21-,22+,23+/m1/s1 Key:QMBJSIBWORFWQT-DFXBJWIESA-N

Chlormadinone acetate (abbreviated as CMA) (INN, USAN, BAN, JAN) (sold under brand names including Clordion, Gestafortin, Lormin, Non-Ovlon, Normenon, Verton, and many others), and also known as 17α-acetoxy-6-chloro-6-dehydroprogesterone, is a steroidal progestin with additional antiandrogen and antigonadotropic (and by extension antiestrogenic) effects. CMA has been used in the treatment of vaginal bleeding, oligomenorrhea, polymenorrhea, hypermenorrhea, secondary amenorrhea, and endometriosis. It has also been used clinically as a hormonal contraceptive, and in part due to its capacity to lower estrogen levels, but also for improved effectiveness in contraception, chlormadinone has frequently been combined with ethinylestradiol for this purpose.

CMA is the acetate ester of chlormadinone, which, in contrast to CMA, was never marketed.

CMA acts predominantly as a potent progestogen, but also as an antiandrogen. Due to its potent actions as a progestogen, CMA also has strong antigonadotropic properties, and thus additional antiandrogen as well as antiestrogen properties.

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