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Gestonorone caproate

Gestonorone caproate
Clinical data
Trade namesDepostat, Primostat
Other namesGestronol 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[1][2][3]
Drug classProgestogen; Progestin; Progestogen ester; Antigonadotropin
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityOral: Low[4]
IM: High[5]
MetabolismReduction (at the C5, C3, and C20 positions)[6]
Metabolites• 19-Norpregnanetriol[6]
• 19-Norpregnanediol-20-one[6]
Elimination half-lifeIM: 7.5 ± 3.1 days[5]
Duration of actionIM: ≥21 days[5]
ExcretionUrine: 28%[5]
Feces: 72%[5]
Identifiers
  • [(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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.013.646 Edit this at Wikidata
Chemical and physical data
FormulaC26H38O4
Molar mass414.586 g·mol−1
3D model (JSmol)
  • CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C(=O)C
  • 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]

  1. ^ 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.
  2. ^ Aronson JK (21 February 2009). Meyler's Side Effects of Endocrine and Metabolic Drugs. Elsevier. pp. 289–. ISBN 978-0-08-093292-7.
  3. ^ 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.
  4. ^ a b Cite error: The named reference pmid4285463 was invoked but never defined (see the help page).
  5. ^ a b c d e f g h Cite error: The named reference BruchhausenDannhardt2013 was invoked but never defined (see the help page).
  6. ^ a b c Cite error: The named reference Springer2013 was invoked but never defined (see the help page).
  7. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1761–1762. ISBN 978-0-8155-1856-3.
  8. ^ Thurston DE (22 November 2006). Chemistry and Pharmacology of Anticancer Drugs. CRC Press. pp. 154–155. ISBN 978-1-4200-0890-6.
  9. ^ Cite error: The named reference Raspé2013 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference SchooneesDe Klerk1969 was invoked but never defined (see the help page).
  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.
  12. ^ Cite error: The named reference Schering1968 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference AubreyKhosla1971 was invoked but never defined (see the help page).
  14. ^ Kaiser R (1960). "Klinische Erfahrungen mit Norprogesteronderivaten". ZBL. Gynäk. 82: 2009.
  15. ^ Cite error: The named reference SubbiahMortensen1973 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  18. ^ a b Cite error: The named reference Micromedex was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference Martindale was invoked but never defined (see the help page).
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