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
SMILES / InChI / InChIKey
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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
InChI Key RDOIQAHITMMDAJ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1976))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
International Nonproprietary Names Click here for help
INN number INN
3098 loperamide
Synonyms Click here for help
Fortasec® | Imodium® | R-18553
Database Links Click here for help
CAS Registry No. 53179-11-6
ChEMBL Ligand CHEMBL841
DrugBank Ligand DB00836
DrugCentral Ligand 1599
GtoPdb PubChem SID 178103790
PubChem CID 3955
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Wikipedia Loperamide