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Record Information
Version3.6
Creation Date2006-10-16 11:41:27 UTC
Update Date2013-02-09 00:13:44 UTC
HMDB IDHMDB04999
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. Apo-Loperamide
  2. Imodium A-D
  3. Imodium A-D Caplets
  4. Kaopectate II
  5. Loperacap
  6. Loperamide hydrochloride
  7. Maalox Anti-Diarrheal
  8. Nu-Loperamide
  9. PMS-Loperamide
  10. Rho-Loperamide
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 IUPAC Nameloperamide
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
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassDiphenylmethanes
Sub ClassN/A
Other Descriptors
  • Phenylpiperidines
  • piperidines(ChEBI)
Substituents
  • Aryl Chloride
  • Carboxamide Group
  • Chlorobenzene
  • Organochloride
  • Phenylpropylamine
  • Piperidine
  • Tertiary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
  • Tertiary Carboxylic Acid Amide
Direct ParentDiphenylmethanes
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.600E-04 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 Area43.78ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.32ChemAxon
Polarizability52.92ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Central Nervous System
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023576
KNApSAcK IDNot Available
Chemspider ID3818
KEGG Compound IDC07080
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLoperamide
NuGOwiki LinkHMDB04999
Metagene LinkHMDB04999
METLIN ID1016
PubChem Compound3955
PDB IDNot Available
ChEBI ID6532
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

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
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Glucose 1,6-bisphosphate synthase using 1,3-bisphosphoglycerate as a phosphate donor and a series of 1-phosphate sugars as acceptors, including glucose 1-phosphate, mannose 1-phosphate, ribose 1-phosphate and deoxyribose 1-phosphate. 5 or 6-phosphosugars are bad substrates, with the exception of glucose 6-phosphate. Also synthesizes ribose 1,5-bisphosphate. Has only low phosphopentomutase and phosphoglucomutase activities.
Gene Name:
PGM2L1
Uniprot ID:
Q6PCE3
Molecular weight:
70441.085