Chemistry:Gemeprost

Short description: Chemical compound

Gemeprost

Clinical data
Trade names	Cervagem
Other names	methyl (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.com	International Drug Names
Pregnancy category	AU: B3
Routes of administration	Pessary
ATC code	G02AD03 (WHO)
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	64318-79-2 Y
PubChem CID	5282237
DrugBank	DB08964 N
ChemSpider	4445416 Y
UNII	45KZB1FOLS
KEGG	D02073 Y
Chemical and physical data
Formula	C23H38O5
Molar mass	394.552 g·mol−1
3D model (JSmol)	Interactive image
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)

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.

External links

• "Gemeprost". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/gemeprost.