Loperamide (CED0003051)

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
Description
Loperamide is an organic compound with the formula C29H33ClN2O2 and an average molecular weight of 477.04 g/mol. Loperamide belongs to the diphenylmethanes, a subclass of benzene and substituted derivatives within the organic compounds. It is utilized as a treatment for diarrhea (PMC11824862, PMC12587445). Among its nine recorded protein targets, it acts as an agonist, blocker, inhibitor, or modulator of the Mu-type opioid receptor (OPRM1), Delta-type opioid receptor (OPRD1), Voltage-dependent P/Q-type calcium channel subunit alpha-1A (CACNA1A), and Pro-opiomelanocortin (POMC), along with five other proteins. The compound has been found in or released from 29 recorded sources. These include aquatic systems and sediments such as seawater, freshwater, groundwater, and surface water, as well as drinking water and water supply sources including bottled, tap, desalinated, and drinking water. It is also present in wastewater, sanitation, and biosolids, including mine wastewater, industrial wastewater, wastewater treatment effluent, and unspecified wastewater. Additionally, it is found in household cleaning and consumer products such as perfumes within detergents and soaps, soap detergents, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites. Other sources include appliances and HVAC/refrigerants like water heaters and water coolers, as well as electrical and electronic equipment including fixed capacitors and their manufacture, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Six more sectors have been recorded. Recorded exposure routes for loperamide include touch, oral, and inhalation.
Contaminant Type
  • Human Neurotoxin
  • PMT
Chemical 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0pi0-5322900000-2bef1a5d1980c912f5c8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00b9-9141830000-374d6457abdd96e40298Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0000900000-673950710672b433271cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-4b7b347a8b8e9dca406cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02t9-0090000000-31f15df976e23e73330aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0000900000-d91d13c4e4665bd5fb5aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0020900000-f1be3181a6918c985ffdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-e5e41346303f41f65688Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-acd8b87c1338e5d0fe25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-81b85f788d14641430fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-3ce1a89454d777268799Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-f101d63ad0bf8e5d2178Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0000900000-d91d13c4e4665bd5fb5aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0020900000-f1be3181a6918c985ffdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-e5e41346303f41f65688Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-acd8b87c1338e5d0fe25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-81b85f788d14641430fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-1a1a49f09397ad090e82Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0090600000-794ea6214c0cd97c73faNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0090300000-e11942e343a28799a5abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-e482bc2c0a1e10520074Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-bbcaf9065d7e1b94c0b4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0000900000-162d4bce153afd6a1f8eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0080900000-c0f1e9709049d5f540c7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02t9-0090000000-3efeeb11d6d724116dbcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0090300000-de31686c81070eeadbbaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-0000900000-c552184a0cc3cba81217Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-0152900000-1622570e5cfe3e4ad7c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-0986200000-36a2062a72571fc2e1fcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-d60ba2c0d78000f3e593Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1211900000-6d663785b1048680810bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03k9-7890100000-9b573ea36bcd5ddcbc35Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0000900000-e45d12c46861786df6d0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1011900000-d43e9f8ebbd555c8a6ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000j-0789200000-be6dfb40772012c99c27Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-fe1db8f7b93b4291a287Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-9012800000-6e44b2210e45b341fbb7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9308100000-30bafefb20e885286219Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
255.0Log mg/kg[140:450]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
diarrheais_treatment_forNot AvailablePMC11824862 , PMC12587445
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
257AntipropulsivesHealthcare, pharmaceuticals & veterinary productsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)2.02408
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)0.856341
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)0.700643
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)2.33548
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)2.64687
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)20.0072
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)21.6421
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)3.73676
Histamine H2 receptor structureClick to view 3D structureHistamine H2 receptorP25021HumansPredicted (SEA)1.71268
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)26.1573
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)19.3845
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)19.7737
Beta-2 adrenergic receptor structureClick to view 3D structureBeta-2 adrenergic receptorP07550HumansPredicted (SEA)3.81461
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)10.4318
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)15.4141
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)18.1389
Histamine H1 receptor structureClick to view 3D structureHistamine H1 receptorP35367HumansPredicted (SEA)18.9952
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)29.7384
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)7.47353
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)15.8034
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)11.2881
Click to view 3D structureAlpha-1B adrenergic receptorP15823Rattus norvegicusPredicted (SEA)4.20386
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)5.52729
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)16.8154
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)115.84
Concentrations
Not Available
External Links
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