Misoprostol

Misoprostol
Clinical data
Trade names	Cytotec, Misodel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a689009
License data	US DailyMed: Misoprostol;
Pregnancy; category	AU: X (High risk); Used for terminating pregnancy;
Routes of; administration	By mouth, rectal, vaginal, under the tongue
ATC code	A02BB01 (WHO) G02AD06 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances) Hospital use only; CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	extensively absorbed
Protein binding	80–90% (active metabolite, misoprostol acid)
Metabolism	Liver (extensive to misoprostic acid)
Elimination half-life	20–40 minutes
Excretion	Urine (80%)
Identifiers
	IUPAC name Methyl 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-4-hydroxy-4-methyloct-1-enyl)-5-oxocyclopentyl)heptanoate;
CAS Number	59122-46-2 ;
PubChem CID	5282381;
IUPHAR/BPS	1936;
DrugBank	DB00929 ;
ChemSpider	4445541 ;
UNII	0E43V0BB57;
KEGG	D00419 ;
ChEMBL	ChEMBL606 ;
CompTox Dashboard (EPA)	DTXSID7020897 ;
ECHA InfoCard	100.190.521
Chemical and physical data
Formula	C22H38O5
Molar mass	382.541 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC[C@](C)(O)C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC;
	InChI InChI=1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,20-,22?/m1/s1 ; Key:OJLOPKGSLYJEMD-URPKTTJQSA-N ;
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Misoprostol is a synthetic prostaglandin medication used to prevent and treat stomach and duodenal ulcers, induce labor, cause an abortion, and treat postpartum bleeding due to poor contraction of the uterus. It is taken by mouth when used to prevent gastric ulcers in people taking nonsteroidal anti-inflammatory drugs (NSAID). For abortions it is typically used in conjunction with mifepristone or methotrexate, but can be used alone. By itself, effectiveness for abortion is between 82% and 100%. Its efficacy with mifepristone is higher, but varies based on gestational age. The misoprostol-only abortion regimen is typically recommended only when mifepristone is not available. For labor induction or abortion, it is taken by mouth, dissolved in the mouth, or placed in the vagina. For postpartum bleeding it may also be used rectally.

Common side effects include diarrhea and abdominal pain. It is in pregnancy category X, meaning that it is known to result in negative outcomes for the fetus if taken during pregnancy. In rare cases, uterine rupture may occur. It is a prostaglandin analogue—specifically, a synthetic prostaglandin E₁ (PGE₁).

Misoprostol was developed in 1973 and first created for the treatment of gastric ulcers. Its first uses for abortion emerged in Latin America in the 1980s, as women noticed miscarriage was a side effect of the medication. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.