Gestrinone

Gestrinone

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	X
Routes of administration	Oral, Intravaginal
ATC code	G03XA02 (WHO)
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal, fecal
Identifiers
IUPAC name (8S,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Synonyms	R-2323, RU-2323
CAS Number	16320-04-0 Y
PubChem CID	27812
ChemSpider	25877 Y
UNII	1421533RCM
KEGG	D04317 Y
ECHA InfoCard	100.210.606
Chemical and physical data
Formula	C21H24O2
Molar mass	308.41 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4\C=C3/C(=C2/C=C\[C@]1([C@@H](CC[C@]1(C#C)O)[C@@H]2CC3)CC)CC4
InChI InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1 Y Key:BJJXHLWLUDYTGC-ANULTFPQSA-N Y

Gestrinone (INN, USAN, BAN) (brand names Dimetriose, Dimetrose, Nemestran), also known as ethylnorgestrienone (i.e., ethyl variant of norgestrienone), is a synthetic steroid of the 19-nortestosterone group that is marketed in Europe, Australia, and Latin America, though not in the United States, and is used primarily in the treatment of endometriosis. It is a potent mixed progestogen and antiprogestogen (i.e., partial agonist of the progesterone receptor (PR) or selective progesterone receptor modulator (SPRM)), an antigonadotropin, a mild androgen and anabolic steroid, and a functional antiestrogen. Gestrinone is described as similar in action and effect to danazol, which is also used in the treatment of endometriosis, but is reported to have fewer androgenic side effects in comparison. Because of its anabolic effects, the use of gestrinone in competition has been banned by the International Olympic Committee.