Gemeprost

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

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)[1]
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
CompTox Dashboard (EPA)	DTXSID40895073
ECHA InfoCard	100.058.869
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)

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]}