Gestonorone caproate

Gestonorone caproate

Clinical data
Trade names	Depostat, Primostat
Routes of administration	Intramuscular
ATC code	G03DA01 (WHO) L02AB03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl) hexanoate
Synonyms	SH-582, SH-80582, NSC-84054; Gestonorone hexanoate, Gestronol hexanoate, Gestronol caproate, Norhydroxyprogesterone caproate; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione hexanoate; 17α-hydroxy-19-norprogesterone hexanoate
CAS Number	1253-28-7
PubChem CID	443881
ChemSpider	391969 Y
ECHA InfoCard	100.016.708
Chemical and physical data
Formula	C26H38O4
Molar mass	414.57752 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C(=O)C
InChI InChI=1S/C26H38O4/c1-4-5-6-7-24(29)30-26(17(2)27)15-13-23-22-10-8-18-16-19(28)9-11-20(18)21(22)12-14-25(23,26)3/h16,20-23H,4-15H2,1-3H3/t20-,21+,22+,23-,25-,26-/m0/s1 Key:XURCMZMFZXXQDJ-UKNJCJGYSA-N

Gestonorone caproate (INN, USAN, JAN) (brand names Depostat, Primostat), also known as gestronol hexanoate (BANM), as well as 17α-hydroxy-19-norprogesterone hexanoate or norhydroxyprogesterone caproate, is a synthetic, steroidal progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups. It is used in the treatment of sex hormone-dependent conditions such as benign prostatic hypertrophy and endometrial cancer. The drug was developed by Schering and has been marketed since at least 1973, and is available widely throughout Europe, including the United Kingdom, and is also marketed in Japan, China, Mexico, and other countries.

Gestonorone caproate is a strong, long-acting, and pure progestogen, possessing no androgenic, anabolic, antiandrogenic, estrogenic, antiestrogenic, corticosteroid, or teratogenic effects. In animals, it is approximately 25 times more potent than progesterone or hydroxyprogesterone caproate. In humans, 100 or 200 mg intramuscular gestonorone caproate is said to be equivalent to 1000 mg intramuscular hydroxyprogesterone caproate. Like other potent progestins, gestonorone caproate possesses potent antigonadotropic activity and is capable of markedly suppressing the gonadal production and circulating levels of sex hormones such as testosterone and estradiol. A clinical study found that 400 mg/week intramuscular gestonorone caproate suppressed testosterone levels by 75% in men. The drug is administered once weekly by intramuscular injection, via which it acts as a depot. Like the closely related progestins hydroxyprogesterone caproate and 19-norprogesterone, gestonorone caproate shows poor activity orally.