misoprostol (methyl ester)   Click here for help

GtoPdb Ligand ID: 1936

Synonyms: Arthrotec® | BRN 4155643 | CCRIS 6859 | Cytotec® | HSDB 3573 | SC 29333
Approved drug
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: misoprostol

misoprostol (methyl ester) is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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 Click here for help
The approved drug misoprostol is indicated for the treatment of ulceration and prophylaxis of ulceration induced by NSAIDs.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
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.