CHEBI:63610 - misoprostol

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ChEBI Name misoprostol
ChEBI ID CHEBI:63610
Definition A diastereoisomeric mixture composed of approximately equal amounts of a double racemate of four of the sixteen possible diastereoisomers of methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate that is racemic prostaglandin E1 which is lacking the hydroxy group at position 15, but which has an additional hydroxy group at position 16. It is a synthetic prostaglandin E1 analogue, used in the treatment of gastric and duodenal ulcers. A weak abortifacient, it is also used for cervical ripening prior to surgical termination of pregnancy. The (11R,16S)-diastereoisomer is the pharmacologically active form.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:6952
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Roles Classification
Application(s): anti-ulcer drug
One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
oxytocic
A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).
abortifacient
A chemical substance that interrupts pregnancy after implantation.
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ChEBI Ontology
Outgoing misoprostol (CHEBI:63610) has part (11R,16R)-misoprostol (CHEBI:63705)
misoprostol (CHEBI:63610) has part (11R,16S)-misoprostol (CHEBI:63695)
misoprostol (CHEBI:63610) has part (11S,16R)-misoprostol (CHEBI:63698)
misoprostol (CHEBI:63610) has part (11S,16S)-misoprostol (CHEBI:63700)
misoprostol (CHEBI:63610) has role abortifacient (CHEBI:50691)
misoprostol (CHEBI:63610) has role anti-ulcer drug (CHEBI:49201)
misoprostol (CHEBI:63610) has role oxytocic (CHEBI:36063)
misoprostol (CHEBI:63610) is a diastereoisomeric mixture (CHEBI:60915)
INNs Sources
misoprostol ChemIDplus
misoprostolum ChemIDplus
Synonyms Sources
(±)-methyl (1R,2R,3R)-3-hydroxy-2-((E)-(4RS)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate ChemIDplus
(11-α,13E)-(±)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester ChemIDplus
Methyl (±)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate ChemIDplus
Brand Names Sources
Arthrotec DrugBank
Cytotec KEGG DRUG
Manual Xrefs Databases
BE827127 Patent
D00419 KEGG DRUG
DB00929 DrugBank
Misoprostol Wikipedia
US3965143 Patent
View more database links
Registry Numbers Types Sources
4155643 Reaxys Registry Number Reaxys
59122-46-2 CAS Registry Number ChemIDplus
59122-46-2 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
10945193 PubMed citation Europe PMC
10949752 PubMed citation Europe PMC
11136959 PubMed citation Europe PMC
1417145 PubMed citation Europe PMC
18690850 PubMed citation Europe PMC
19740175 PubMed citation Europe PMC
2109814 PubMed citation Europe PMC
3080288 PubMed citation Europe PMC
Last Modified
22 February 2017