loperamide   Click here for help

GtoPdb Ligand ID: 7215

Synonyms: Fortasec® | Imodium® | R-18553
Approved drug
loperamide is an approved drug (FDA (1976))
Compound class: Synthetic organic
Comment: Loperamide is an opioid-receptor agonist used as an anti-diarrheal agent. Although unreported previously, recent clinical cases of severe cardiotoxicity (and death) due to high-dose loperamide abuse have been reported [2-3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 43.78
Molecular weight 476.22
XLogP 5.46
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(cc1)C1(O)CCN(CC1)CCC(C(=O)N(C)C)(c1ccccc1)c1ccccc1
Isomeric SMILES Clc1ccc(cc1)C1(O)CCN(CC1)CCC(C(=O)N(C)C)(c1ccccc1)c1ccccc1
InChI InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3
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Summary of Clinical Use Click here for help
Used to treat diarrhea.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
This drug slows peristalsis, allowing the gut to re-absorb more fluid and nutrients. This is achieved through calcium channel block and activation of μ opioid receptors. As this reduces the overall stool mass produced the drug is used for this effect in patients with ileostomy.
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