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;
CompTox Dashboard (EPA)	DTXSID40871837 ;
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.^[5]^[3]^[7]^[1]^[8] It is given by injection into muscle typically once a week.^[4]

Side effects of gestonorone caproate include worsened glucose tolerance, decreased libido in men, and injection site reactions.^[5] 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.^[9]^[10] It has no other important hormonal activity.^[5]^[11]^[12]^[13]

Gestonorone caproate was discovered in 1960 and was introduced for medical use by 1973.^[14]^[15] 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.^[1]^[16]^[17]^[18] 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.^[18]^[19]

^ ^a ^b ^c Muller (19 June 1998). European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 338–. ISBN 978-3-7692-2114-5.
^ Aronson JK (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs. Elsevier. pp. 289–. ISBN 978-0-08-093292-7.
^ ^a ^b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 132–. ISBN 978-94-011-4439-1.
^ ^a ^b Cite error: The named reference pmid4285463 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h Cite error: The named reference BruchhausenDannhardt2013 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference Springer2013 was invoked but never defined (see the help page).
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1761–1762. ISBN 978-0-8155-1856-3.
^ Thurston DE (22 November 2006). Chemistry and Pharmacology of Anticancer Drugs. CRC Press. pp. 154–155. ISBN 978-1-4200-0890-6.
^ Cite error: The named reference Raspé2013 was invoked but never defined (see the help page).
^ Cite error: The named reference SchooneesDe Klerk1969 was invoked but never defined (see the help page).
^ Horský J, Presl J (1981). "Genital Cycle". In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Developments in Obstetrics and Gynecology. Springer Science & Business Media. pp. 70–129. doi:10.1007/978-94-009-8195-9_11. ISBN 978-94-009-8195-9. Gestonorone caproate is a depot gestagen, five times more potent than 17α-hydroxyprogesterone caproate.
^ Cite error: The named reference Schering1968 was invoked but never defined (see the help page).
^ Cite error: The named reference AubreyKhosla1971 was invoked but never defined (see the help page).
^ Kaiser R (1960). "Klinische Erfahrungen mit Norprogesteronderivaten". ZBL. Gynäk. 82: 2009.
^ Cite error: The named reference SubbiahMortensen1973 was invoked but never defined (see the help page).
^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Micromedex was invoked but never defined (see the help page).
^ Cite error: The named reference Martindale was invoked but never defined (see the help page).

[Muller1998-1] Muller (19 June 1998). European Drug Index: European Drug Registrations (Fourth ed.). CRC Press. pp. 338–. ISBN 978-3-7692-2114-5.

[Aronson2009-2] Aronson JK (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs. Elsevier. pp. 289–. ISBN 978-0-08-093292-7.

[MortonHall2012-3] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 132–. ISBN 978-94-011-4439-1.

[pmid4285463-4] Cite error: The named reference pmid4285463 was invoked but never defined (see the help page).

[BruchhausenDannhardt2013-5] ^ ^a ^b ^c ^d ^e ^f ^g ^h Cite error: The named reference BruchhausenDannhardt2013 was invoked but never defined (see the help page).

[Springer2013-6] Cite error: The named reference Springer2013 was invoked but never defined (see the help page).

[Publishing2013-7] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1761–1762. ISBN 978-0-8155-1856-3.

[Thurston2006-8] Thurston DE (22 November 2006). Chemistry and Pharmacology of Anticancer Drugs. CRC Press. pp. 154–155. ISBN 978-1-4200-0890-6.

[Raspé2013-9] Cite error: The named reference Raspé2013 was invoked but never defined (see the help page).

[SchooneesDe_Klerk1969-10] Cite error: The named reference SchooneesDe Klerk1969 was invoked but never defined (see the help page).

[HorskyPresl1981a-11] Horský J, Presl J (1981). "Genital Cycle". In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Developments in Obstetrics and Gynecology. Springer Science & Business Media. pp. 70–129. doi:10.1007/978-94-009-8195-9_11. ISBN 978-94-009-8195-9. Gestonorone caproate is a depot gestagen, five times more potent than 17α-hydroxyprogesterone caproate.

[Schering1968-12] Cite error: The named reference Schering1968 was invoked but never defined (see the help page).

[AubreyKhosla1971-13] Cite error: The named reference AubreyKhosla1971 was invoked but never defined (see the help page).

[Kaiser1960-14] Kaiser R (1960). "Klinische Erfahrungen mit Norprogesteronderivaten". ZBL. Gynäk. 82: 2009.

[SubbiahMortensen1973-15] Cite error: The named reference SubbiahMortensen1973 was invoked but never defined (see the help page).

[IndexNominum2000-16] Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).

[Drugs.com-17] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[Micromedex-18] Cite error: The named reference Micromedex was invoked but never defined (see the help page).

[Martindale-19] Cite error: The named reference Martindale was invoked but never defined (see the help page).

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