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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-16 11:41:27 UTC
Update Date2022-03-07 02:49:24 UTC
HMDB IDHMDB0004999
Secondary Accession Numbers
  • HMDB04999
Metabolite Identification
Common NameLoperamide
DescriptionLoperamide is an opioid receptor agonist and acts on the mu opioid receptors in the myenteric plexus large intestines; it does not affect the central nervous system like other opioids; Loperamide usually as hydrochloride, is a drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. In most countries it is available generically under brand names such as Lopex, Imodium, Dimor and Pepto Diarrhea Control; Treatment should be avoided in the presence of fever or if the stool is bloody. Treatment is not recommended for patients who could suffer detrimental effects from rebound constipation. If there is a suspicion of diarrhea associated with organisms that can penetrate the intestinal walls, such as E. coli O157:H7 or salmonella, loperamide is contraindicated; Loperamide, usually as hydrochloride, is a drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. In most countries it is available generically under brand names such as Lopex, Imodium, Dimor and Pepto Diarrhea Control; it does not affect the central nervous system like other opioids; One 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; Loperamide is an opioid receptor agonist and acts on the mu opioid receptors in the myenteric plexus large intestines.
Structure
Data?1582752338
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 Weight477.038
Monoisotopic Molecular Weight476.223056017
IUPAC Name4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
Traditional Nameimodium
CAS Registry Number53179-11-6
SMILES
CN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
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 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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM222.730932474
[M+H]+Not Available219.403http://allccs.zhulab.cn/database/detail?ID=AllCCS00000773
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+204.17730932474
DeepCCS[M-H]-201.81230932474
DeepCCS[M-2H]-234.69730932474
DeepCCS[M+Na]+210.65730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LoperamideCN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C14573.5Standard polar33892256
LoperamideCN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C13640.0Standard non polar33892256
LoperamideCN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C13750.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Loperamide,1TMS,isomer #1CN(C)C(=O)C(CCN1CCC(O[Si](C)(C)C)(C2=CC=C(Cl)C=C2)CC1)(C1=CC=CC=C1)C1=CC=CC=C13646.4Semi standard non polar33892256
Loperamide,1TBDMS,isomer #1CN(C)C(=O)C(CCN1CCC(O[Si](C)(C)C(C)(C)C)(C2=CC=C(Cl)C=C2)CC1)(C1=CC=CC=C1)C1=CC=CC=C13848.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Loperamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi0-5322900000-2bef1a5d1980c912f5c82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Loperamide GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9141830000-374d6457abdd96e402982017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Loperamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Loperamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-0000900000-673950710672b433271c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-0090000000-4b7b347a8b8e9dca406c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-02t9-0090000000-31f15df976e23e73330a2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-004i-0000900000-d91d13c4e4665bd5fb5a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-004i-0020900000-f1be3181a6918c985ffd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-014i-0090000000-e5e41346303f41f656882012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-014i-0090000000-acd8b87c1338e5d0fe252012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-0090000000-81b85f788d14641430fd2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-014i-0090000000-3ce1a89454d7772687992012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-03di-0090000000-f101d63ad0bf8e5d21782012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ , positive-QTOFsplash10-004i-0000900000-d91d13c4e4665bd5fb5a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ , positive-QTOFsplash10-004i-0020900000-f1be3181a6918c985ffd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ , positive-QTOFsplash10-014i-0090000000-e5e41346303f41f656882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ , positive-QTOFsplash10-014i-0090000000-acd8b87c1338e5d0fe252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QQ , positive-QTOFsplash10-014i-0090000000-81b85f788d14641430fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-IT , positive-QTOFsplash10-014i-0090000000-1a1a49f09397ad090e822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide , positive-QTOFsplash10-016r-0090600000-794ea6214c0cd97c73fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide LC-ESI-QFT , positive-QTOFsplash10-016r-0090300000-e11942e343a28799a5ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loperamide 40V, Positive-QTOFsplash10-014i-0090000000-e482bc2c0a1e105200742021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loperamide 10V, Positive-QTOFsplash10-0a6r-0000900000-c552184a0cc3cba812172017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loperamide 20V, Positive-QTOFsplash10-0a6r-0152900000-1622570e5cfe3e4ad7c22017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loperamide 40V, Positive-QTOFsplash10-000f-0986200000-36a2062a72571fc2e1fc2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loperamide 10V, Negative-QTOFsplash10-004i-0000900000-d60ba2c0d78000f3e5932017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loperamide 20V, Negative-QTOFsplash10-004i-1211900000-6d663785b1048680810b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loperamide 40V, Negative-QTOFsplash10-03k9-7890100000-9b573ea36bcd5ddcbc352017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0024 +/- 0.0008 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00836
Phenol Explorer Compound IDNot Available
FooDB IDFDB023576
KNApSAcK IDNot Available
Chemspider ID3818
KEGG Compound IDC07080
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLoperamide
METLIN ID1016
PubChem Compound3955
PDB IDNot Available
ChEBI ID6532
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChu, 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
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:14586389 ]
  2. 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. [PubMed:11014404 ]
  3. 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. [PubMed:6797827 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of subunits
Gene Name:
GRIN2A
Uniprot ID:
Q12879
Molecular weight:
165281.2
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:
GRIN2C
Uniprot ID:
Q14957
Molecular weight:
134531.1
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:
GRIN2B
Uniprot ID:
Q13224
Molecular weight:
166365.9
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:
GRIN2D
Uniprot ID:
O15399
Molecular weight:
143750.7
General function:
Involved in calcium ion binding
Specific function:
Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:
CALM1
Uniprot ID:
P62158
Molecular weight:
16837.5
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular weight:
40412.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
General function:
Involved in catalytic activity
Specific function:
Hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions
Gene Name:
MPG
Uniprot ID:
P29372
Molecular weight:
32868.4
General function:
Involved in ion channel activity
Specific function:
Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1A gives rise to P and/or Q-type calcium currents. P/Q-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by the funnel toxin (Ftx) and by the omega-agatoxin- IVA (omega-Aga-IVA). They are however insensitive to dihydropyridines (DHP), and omega-conotoxin-GVIA (omega-CTx-GVIA)
Gene Name:
CACNA1A
Uniprot ID:
O00555
Molecular weight:
282362.4

Only showing the first 10 proteins. There are 11 proteins in total.