Gestonorone caproate

Gestonorone caproate
Clinical data
Trade names	Depostat, Primostat
Other names	Gestronol hexanoate; Norhydroxyprogesterone caproate; SH-582; SH-80582; NSC-84054; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione hexanoate; 17α-Hydroxy-19-norprogesterone hexanoate
Routes of; administration	Intramuscular injection
Drug class	Progestogen; Progestin; Progestogen ester; Antigonadotropin
ATC code	G03DA01 (WHO) ; L02AB03 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Oral: Low; IM: High
Metabolism	Reduction (at the C5, C3, and C20 positions)
Metabolites	• 19-Norpregnanetriol; • 19-Norpregnanediol-20-one
Elimination half-life	IM: 7.5 ± 3.1 days
Duration of action	IM: ≥21 days
Excretion	Urine: 28%; Feces: 72%
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] hexanoate;
CAS Number	1253-28-7;
PubChem CID	443881;
DrugBank	DB14677;
ChemSpider	391969 ;
UNII	U38E620NS6;
KEGG	D01159;
ChEBI	CHEBI:31650;
ChEMBL	ChEMBL2107389;
ECHA InfoCard	100.013.646
Chemical and physical data
Formula	C26H38O4
Molar mass	414.586 g·mol−1
3D model (JSmol)	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, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of enlarged prostate and cancer of the endometrium. It is given by injection into muscle typically once a week.

Side effects of gestonorone caproate include worsened glucose tolerance, decreased libido in men, and injection site reactions. Gestonorone caproate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has no other important hormonal activity.

Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973. It has been used widely throughout Europe, including in the United Kingdom, and has also been marketed in certain other countries such as Japan, China, and Mexico. However, it has since mostly been discontinued, and it remains available today only in a handful of countries, including the Czech Republic, Japan, Mexico, and Russia.

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