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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2D Structure
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Physico-chemical Properties
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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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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1988))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
Is prodrug? Yes
Active form misoprostol (free acid form)
IUPAC Name Click here for help
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
International Nonproprietary Names Click here for help
INN number INN
5154 misoprostol
Synonyms Click here for help
Arthrotec® | BRN 4155643 | CCRIS 6859 | Cytotec® | HSDB 3573 | SC 29333
Database Links Click here for help
CAS Registry No. 59122-46-2 (source: Scifinder)
ChEBI CHEBI:63610
ChEMBL Ligand CHEMBL606
DrugBank Ligand DB00929
DrugCentral Ligand 1817
GtoPdb PubChem SID 135650611
PubChem CID 5282381
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Wikipedia Misoprostol

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Tocris
Misoprostol
Cat. No. 2297