misoprostol (methyl ester)

Ligand id: 1936

Name: misoprostol (methyl ester)

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View more information in the IUPHAR Pharmacology Education Project: misoprostol

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 14
Topological polar surface area 83.83
Molecular weight 382.27
XLogP 3.57
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1988))
Is prodrug? Yes
Active form misoprostol (free acid form)
IUPAC Name
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
International Nonproprietary Names
INN number INN
5154 misoprostol
Synonyms
Arthrotec® | BRN 4155643 | CCRIS 6859 | Cytotec® | HSDB 3573 | SC 29333
Database Links
CAS Registry No. 59122-46-2 (source: Scifinder)
ChEBI CHEBI:63610
ChEMBL Ligand CHEMBL606
DrugBank Ligand DB00929
PubChem CID 5282381
Search Google for chemical match using the InChIKey OJLOPKGSLYJEMD-URPKTTJQSA-N
Search Google for chemicals with the same backbone OJLOPKGSLYJEMD
Search PubMed clinical trials misoprostol
Search PubMed titles misoprostol
Search PubMed titles/abstracts misoprostol
Search UniChem for chemical match using the InChIKey OJLOPKGSLYJEMD-URPKTTJQSA-N
Search UniChem for chemicals with the same backbone OJLOPKGSLYJEMD
Wikipedia Misoprostol
Comments
The INN-assigned approved drug misoprostol is a racemic mixture of two epimers and their enantiomers. For more information, please see the ChEBI link above. Note that the INN-assigned structure represents the methyl ester form of the compound as which the drug is administered. The drug is then converted in vivo to the active metabolite misoprostol (free acid form).