Loperamide hydrochlorideProduct ingredient for Loperamide

Show full entry for Loperamide
Name
Loperamide hydrochloride
Drug Entry
Loperamide

Loperamide is an anti-diarrheal agent that is available as an over-the-counter product for treating diarrhea.7 The drug was first synthesized in 1969 and used medically in 1976.1 It is a highly lipophilic synthetic phenylpiperidine opioid that works by binding to mu-opioid receptors on intestinal muscles to decrease intestinal motility and electrolyte loss.1 Loperamide has a chemical structure that is similar to diphenoxylate and haloperidol;2 however, loperamide works on mu (μ)-opioid receptors to mediate its pharmacological actions.1

See full entry for Loperamide
Accession Number
DBSALT000709
Structure
Similar Structures
Synonyms
Loperamide HCl
UNII
77TI35393C
CAS Number
34552-83-5
Weight
Average: 513.498
Monoisotopic: 512.199733756
Chemical Formula
C29H34Cl2N2O2
InChI Key
PGYPOBZJRVSMDS-UHFFFAOYSA-N
InChI
InChI=1S/C29H33ClN2O2.ClH/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;1H
IUPAC Name
4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide hydrochloride
SMILES
Cl.CN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1
PubChem Compound
71420
ChemSpider
64510
ChEBI
6533
ChEMBL
CHEMBL1707
Wikipedia
Loperamide
Predicted Properties
PropertyValueSource
Water Solubility0.00086 mg/mLALOGPS
logP4.44ALOGPS
logP4.77Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)13.96Chemaxon
pKa (Strongest Basic)9.41Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area43.78 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity139.32 m3·mol-1Chemaxon
Polarizability53.13 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon