Gemeprost

Gemeprost (16, 16-dimethyl-trans-delta2 PGE1 methyl ester) is an analogue of prostaglandin E1.

Gemeprost
Clinical data
Trade namesCervagem
Other namesmethyl (E)-7-[(1R,2S,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4,4-dimethyl-oct-1-enyl]-5-oxo-cyclopentyl]hept-2-enoate
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • AU: B3
Routes of
administration		Pessary
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only) [1]
Identifiers
IUPAC name
  • methyl (2E,11α,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.058.869
Chemical and physical data
FormulaC23H38O5
Molar mass394.552 g·mol−1
3D model (JSmol)
SMILES
  • O=C1C[C@@H](O)[C@H](/C=C/[C@@H](O)C(C)(C)CCCC)[C@H]1CCCC\C=C\C(=O)OC
InChI
  • InChI=1S/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13+/t17-,18-,20-,21-/m1/s1 Y
  • Key:KYBOHGVERHWSSV-VNIVIJDLSA-N Y
 NY (what is this?)  (verify)

Clinical use

It is used as a treatment for obstetric bleeding.

It is used with mifepristone to terminate pregnancy up to 24 weeks gestation.[2]

Side effects

Vaginal bleeding, cramps, nausea, vomiting,[3] loose stools or diarrhea,[3] headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild pyrexia.[3] Rare: Uterine rupture, severe hypotension, coronary spasms with subsequent myocardial infarctions.

References
  1. "Cervagem 1 mg Pessary - Summary of Product Characteristics (SmPC)". (emc). 16 August 2019. Retrieved 7 September 2020.
  2. Bartley J, Brown A, Elton R, Baird DT (October 2001). "Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation". Human Reproduction. 16 (10): 2098–102. doi:10.1093/humrep/16.10.2098. PMID 11574498.
  3. Aronson, J. K. (2015). Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions. Elsevier Science. p. 524. ISBN 978-0-4445-3716-4.
  • "Gemeprost". Drug Information Portal. U.S. National Library of Medicine.
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