misoprostol

Term ID

CHEBI:63610

Synonyms

• (+-)-methyl (1R,2R,3R)-3-hydroxy-2-((E)-(4RS)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate
• (11-alpha,13E)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester
• Arthrotec
• Cytotec
• Methyl (+-)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate
• misoprostol
• misoprostolum

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.

References

• cas:59122-46-2
• drugbank:DB00929
• kegg.drug:D00419
• patent:BE827127
• patent:US3965143
• pubmed:10945193
• pubmed:10949752
• pubmed:11136959
• pubmed:1417145
• pubmed:18690850
• pubmed:19740175
• pubmed:2109814
• pubmed:3080288
• reaxys:4155643
• wikipedia.en:Misoprostol

Ontology

ChEBI  ( EBI )

Resources

CTD