Structure via PubChem · Public domain (PubChem)
misoprostol
Sign in to saveAlso known as BRN 4155643, CCRIS 6859, HSDB 3573, SC 29333, (11alpha,13E)-(+)-11alpha,16-dihydroxy-16-methyl-9-oxoprost-13E-en-1-oic acid methyl ester
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
Key facts
- Drug.ATC_suffix
- BB01
- Drug.legal_AU
- S4
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 456483721
- Drug.image
- Misoprostol.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.tradename
- Cytotec, Misodel, others
- Drug.MedlinePlus
- a689009
- Drug.DailyMedID
- Misoprostol
- Drug.pregnancy_AU
- X
- Drug.pregnancy_category
- Used for terminating pregnancy
- Drug.routes_of_administration
- By mouth, rectal, intravaginal, sublingual
- Drug.ATC_prefix
- A02
- Drug.legal_BR
- C1
- Drug.legal_BR_comment
- Hospital use only
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C22H38O5
- Molecular weight
- 382.5 g/mol
- IUPAC name
- methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
- SMILES
- CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OC)O)O
- InChIKey
- OJLOPKGSLYJEMD-URPKTTJQSA-N
- XLogP
- 3.7
- Polar surface area
- 83.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
6,677 papersvia PubMed
Wikidata facts
- Mass
- 382.272
Show 7 more facts
- chemical formula
- C₂₂H₃₈O₅
- defined daily dose
- 0.8
- World Health Organisation international non-proprietary name
- misoprostol
- isomeric SMILES
- CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OC)O)O
- canonical SMILES
- CCCCC(C)(CC=CC1C(CC(=O)C1CCCCCCC(=O)OC)O)O
- Commons category
- Misoprostol
- stylized name
- miSOPROStol
Sources (7)
via Wikidata · CC0
~15 min read
Article
17 sectionsContents
- Medical uses
- Ulcer prevention
- Labor induction
- Myomectomy
- Abortion
- Early pregnancy loss
- Postpartum bleeding
- Insertion of intrauterine contraceptive device
- Other
- Adverse effects
- Contraindications
- Pharmacology
- Mechanism of action
- Society and culture
- Latin America
- Black market
- References
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).