Loperamide (CHEM018173)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2016-05-22 05:02:38 UTC
Update Date2026-08-22 09:03:25 UTC
Accession NumberCHEM018173
Identification
Common NameLoperamide
ClassSmall Molecule
DescriptionOne of the long-acting synthetic antidiarrheals; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Human Neurotoxin
  • PMT
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
LoperamidaChEBI
LoperamidumChEBI
DiamideKegg
Apo-loperamideHMDB
Imodium a-DHMDB
Imodium a-D capletsHMDB
Kaopectate IIHMDB
LoperacapHMDB
Loperamide hydrochlorideHMDB
Maalox anti-diarrhealHMDB
Nu-loperamideHMDB
PMS-LoperamideHMDB
Rho-loperamideHMDB
Hydrochloride, loperamideHMDB
ImodiumHMDB
Monohydrochloride, loperamideHMDB
Loperamide monohydrochlorideHMDB
Chemical FormulaC29H33ClN2O2
Average Molecular Mass477.038 g/mol
Monoisotopic Mass476.223 g/mol
CAS Registry Number53179-11-6
IUPAC Name4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
Traditional Nameimodium
SMILESCN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=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 KeyRDOIQAHITMMDAJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylpiperidine
  • Phenylacetamide
  • Chlorobenzene
  • Aralkylamine
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Piperidine
  • N-acyl-amine
  • Tertiary carboxylic acid amide
  • Tertiary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00086 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.32 m³·mol⁻¹ChemAxon
Polarizability52.59 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-5322900000-2bef1a5d1980c912f5c8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9141830000-374d6457abdd96e40298Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0000900000-673950710672b433271cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-0090000000-4b7b347a8b8e9dca406cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02t9-0090000000-31f15df976e23e73330aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-0000900000-d91d13c4e4665bd5fb5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004i-0020900000-f1be3181a6918c985ffdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-0090000000-e5e41346303f41f65688Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-0090000000-acd8b87c1338e5d0fe25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-0090000000-81b85f788d14641430fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-014i-0090000000-3ce1a89454d777268799Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0090000000-f101d63ad0bf8e5d2178Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0000900000-d91d13c4e4665bd5fb5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0020900000-f1be3181a6918c985ffdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-e5e41346303f41f65688Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-acd8b87c1338e5d0fe25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-81b85f788d14641430fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-014i-0090000000-1a1a49f09397ad090e82Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-016r-0090600000-794ea6214c0cd97c73faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-016r-0090300000-e11942e343a28799a5abSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0090000000-e482bc2c0a1e10520074Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0000900000-c552184a0cc3cba81217Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0152900000-1622570e5cfe3e4ad7c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0986200000-36a2062a72571fc2e1fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d60ba2c0d78000f3e593Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1211900000-6d663785b1048680810bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-7890100000-9b573ea36bcd5ddcbc35Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00836
HMDB IDHMDB0004999
FooDB IDFDB023576
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1016
PDB IDNot Available
Wikipedia LinkLoperamide
Chemspider ID3818
ChEBI ID6532
PubChem Compound ID3955
Kegg Compound IDC07080
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Chu, Chi-Ya; Hsu, Li-Ying; Wang, Mei-Li; Hsu, Kuo-Ying. Synthesis of the new antidiarrheal drug-loperamide. Huadong Huagong Xueyuan Xuebao (1981), (1), 143-6. CODEN: HHKPDM ISSN:0253-9683. CAN 95:115232 AN 1981:515232
2. Pauli-Magnus C, Feiner J, Brett C, Lin E, Kroetz DL: No effect of MDR1 C3435T variant on loperamide disposition and central nervous system effects. Clin Pharmacol Ther. 2003 Nov;74(5):487-98.
3. Sadeque AJ, Wandel C, He H, Shah S, Wood AJ: Increased drug delivery to the brain by P-glycoprotein inhibition. Clin Pharmacol Ther. 2000 Sep;68(3):231-7.
4. Caldara R, Testori GP, Ferrari C, Romussi M, Rampini P, Borzio M, Barbieri C: Effect of loperamide, a peripheral opiate agonist, on circulating glucose, free fatty acids, insulin, C-peptide and pituitary hormones in healthy man. Eur J Clin Pharmacol. 1981;21(3):185-8.
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15900907
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19034106
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24398461