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Gemeprost

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Chemical compound Pharmaceutical compound
Gemeprost
Clinical data
Trade namesCervagem
Other namesmethyl (E)-7--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)
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 Edit this at Wikidata
Chemical and physical data
FormulaC23H38O5
Molar mass394.552 g·mol
3D model (JSmol)
SMILES
  • O=C1C(O)(/C=C/(O)C(C)(C)CCCC)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
  • Key:KYBOHGVERHWSSV-VNIVIJDLSA-N
  (what is this?)  (verify)

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

Clinical use

It is used as a treatment for obstetric bleeding.

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

Side effects

Vaginal bleeding, cramps, nausea, vomiting, loose stools or diarrhea, headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild pyrexia. 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.

External links

  • "Gemeprost". Drug Information Portal. U.S. National Library of Medicine.
Eicosanoids
Precursor
Prostanoids
Prostaglandins (PG)
Precursor
Active
D/J
E/F
I
Thromboxanes (TX)
Leukotrienes (LT)
Precursor
Initial
SRS-A
Eoxins (EX)
Precursor
Eoxins
Nonclassic
By function
Uterotonics/labor inducers/oxytocics (G02A)
Cervical ripening
Ergot alkaloids
Prostaglandins and
analogues
Contraction induction
Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F2α)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators
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