loperamide   

GtoPdb Ligand ID: 7215

Synonyms: Fortasec® | Imodium® | R-18553
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
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
SMILES / InChI / InChIKey
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
InChI Key RDOIQAHITMMDAJ-UHFFFAOYSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
μ receptor Hs Agonist Agonist 9.3 pKi - 1
pKi 9.3 (Ki 5.3x10-10 M) [1]