Gemeprost

Chemical compound
  • AU: B3
Routes of
administrationPessaryATC code
  • G02AD03 (WHO)
Legal statusLegal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)[1]
Identifiers
  • methyl (2E,11α,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
CAS Number
  • 64318-79-2 checkY
PubChem CID
  • 5282237
DrugBank
  • DB08964 ☒N
ChemSpider
  • 4445416 checkY
UNII
  • 45KZB1FOLS
KEGG
  • D02073 checkY
CompTox Dashboard (EPA)
  • DTXSID40895073 Edit this at Wikidata
ECHA InfoCard100.058.869 Edit this at WikidataChemical and physical dataFormulaC23H38O5Molar mass394.552 g·mol−13D model (JSmol)
  • Interactive image
  • 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 checkY
  • Key:KYBOHGVERHWSSV-VNIVIJDLSA-N checkY
 ☒NcheckY (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.[citation needed]

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.[citation needed]

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. ^ a b c 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.
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PrecursorProstanoids
Prostaglandins (PG)
Precursor
  • H2
Active
D/J
  • D2
E/F
  • E2 (Dinoprostone)
  • E1 (Alprostadil)
  • F (Dinoprost):
I
  • I2 (Prostacyclin/Epoprostenol):
Thromboxanes (TX)
  • A2
  • B2
Leukotrienes (LT)
Precursor
Initial
  • A4
  • B4
SRS-A
  • C4
  • D4
  • E4
Eoxins (EX)
Precursor
  • Arachidonic acid 15-hydroperoxide
Eoxins
  • A4
  • C4
  • D4
  • E4
Nonclassic
By function
  • labor stimulation:
    • PGE2 (Dinoprostone)
    • PGF (Dinoprost)
  • v
  • t
  • e
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
  • Antagonists: AH-6809
  • ONO-8130
  • SC-19220
  • SC-51089
  • SC-51322
EP2Tooltip Prostaglandin EP2 receptor
  • Antagonists: AH-6809
  • PF-04418948
  • TG 4-155
EP3Tooltip Prostaglandin EP3 receptor
  • Antagonists: L-798106
EP4Tooltip Prostaglandin EP4 receptor
  • Antagonists: Grapiprant
  • GW-627368
  • L-161982
  • ONO-AE3-208
Unsorted
  • Agonists: 16,16-Dimethyl Prostaglandin E2
  • Aganepag
  • Carboprost
  • Evatanepag
  • Gemeprost
  • Nocloprost
  • Omidenepag
  • Prostaglandin F (dinoprost)
  • Simenepag
  • Taprenepag
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
  • Antagonists: RO1138452
TP (TXA2)Tooltip Thromboxane receptor
  • Agonists: Carbocyclic thromboxane A2
  • I-BOP
  • Thromboxane A2
  • U-46619
  • Vapiprost
Unsorted
  • Arbaprostil
  • Ataprost
  • Ciprostene
  • Clinprost
  • Cobiprostone
  • Delprostenate
  • Deprostil
  • Dimoxaprost
  • Doxaprost
  • Ecraprost
  • Eganoprost
  • Enisoprost
  • Eptaloprost
  • Esuberaprost
  • Etiproston
  • Fenprostalene
  • Flunoprost
  • Froxiprost
  • Lanproston
  • Limaprost
  • Luprostiol
  • Meteneprost
  • Mexiprostil
  • Naxaprostene
  • Nileprost
  • Nocloprost
  • Ornoprostil
  • Oxoprostol
  • Penprostene
  • Pimilprost
  • Piriprost
  • Posaraprost
  • Prostalene
  • Rioprostil
  • Rivenprost
  • Rosaprostol
  • Spiriprostil
  • Tiaprost
  • Tilsuprost
  • Tiprostanide
  • Trimoprostil
  • Viprostol
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
HQL-79
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators
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