Human Metabolome Database Version 3.5

Showing metabocard for Loperamide (HMDB04999)

Record Information
Version 3.5
Creation Date 2006-10-16 05:41:27 -0600
Update Date 2013-02-08 17:13:44 -0700
HMDB ID HMDB04999
Secondary Accession Numbers None
Metabolite Identification
Common Name Loperamide
Description Loperamide 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C29H33ClN2O2
Average Molecular Weight 477.038
Monoisotopic Molecular Weight 476.223056017
IUPAC Name 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide
Traditional IUPAC Name loperamide
CAS Registry Number 53179-11-6
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 Key RDOIQAHITMMDAJ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Diphenylmethanes
Sub Class N/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 Parent Diphenylmethanes
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 8.600E-04 g/L ALOGPS
LogP 4.44 ALOGPS
LogP 4.77 ChemAxon
LogS -5.74 ALOGPS
pKa (strongest acidic) 13.96 ChemAxon
pKa (strongest basic) 9.41 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 43.78 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 139.32 ChemAxon
Polarizability 52.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Central Nervous System
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0024 +/- 0.0008 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023576
KNApSAcK ID Not Available
Chemspider ID 3818 Link_out
KEGG Compound ID C07080 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Loperamide Link_out
NuGOwiki Link HMDB04999 Link_out
Metagene Link HMDB04999 Link_out
METLIN ID 1016 Link_out
PubChem Compound 3955 Link_out
PDB ID Not Available
ChEBI ID 6532 Link_out
References
Synthesis Reference 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
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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamate [NMDA] receptor subunit epsilon-1
Reactions: Not Available
Gene Name: GRIN2A
Uniprot ID: Q12879 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamate [NMDA] receptor subunit epsilon-3
Reactions: Not Available
Gene Name: GRIN2C
Uniprot ID: Q14957 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamate [NMDA] receptor subunit epsilon-2
Reactions: Not Available
Gene Name: GRIN2B
Uniprot ID: Q13224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutamate [NMDA] receptor subunit epsilon-4
Reactions: Not Available
Gene Name: GRIN2D
Uniprot ID: O15399 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Calmodulin
Reactions: Not Available
Gene Name: CALM1
Uniprot ID: P62158 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta-type opioid receptor
Reactions: Not Available
Gene Name: OPRD1
Uniprot ID: P41143 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Mu-type opioid receptor
Reactions: Not Available
Gene Name: OPRM1
Uniprot ID: P35372 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: DNA-3-methyladenine glycosylase
Reactions: Not Available
Gene Name: MPG
Uniprot ID: P29372 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Voltage-dependent P/Q-type calcium channel subunit alpha-1A
Reactions: Not Available
Gene Name: CACNA1A
Uniprot ID: O00555 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose 1,6-bisphosphate synthase
Reactions: Not Available
Gene Name: PGM2L1
Uniprot ID: Q6PCE3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA