misoprostol (methyl ester)   

GtoPdb Ligand ID: 1936

Synonyms: Arthrotec® | BRN 4155643 | CCRIS 6859 | Cytotec® | HSDB 3573 | SC 29333
misoprostol (methyl ester) is an approved drug (FDA (1988))
Compound class: Synthetic organic
Comment: 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).
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2D Structure
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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
SMILES / InChI / InChIKey
Canonical SMILES CCCCC(CC=CC1C(O)CC(=O)C1CCCCCCC(=O)OC)(O)C
Isomeric SMILES CCCCC(C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC)(O)C
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
InChI Key OJLOPKGSLYJEMD-URPKTTJQSA-N
No information available.
Summary of Clinical Use
The approved drug misoprostol is indicated for the treatment of ulceration and prophylaxis of ulceration induced by NSAIDs.
Mechanism Of Action and Pharmacodynamic Effects
Metabolised to active free acid form in vivo. Misoprostol is a prostaglandin analogue. In the stomach, misoprostol acts on gastric parietal cells, inhibiting the secretion of gastric acid by G-protein coupled receptor-mediated inhibition of adenylate cyclase. This leads to decreased proton pump activity at the apical surface of the parietal cell (i.e. decreased acid secretion). It binds to myometrial cells to cause strong myometrial contractions leading to expulsion of tissue. This agent also causes cervical ripening with softening and dilation of the cervix.