Human Metabolome Database Version 3.5

Showing metabocard for Levamisole (HMDB14986)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:32:43 -0700
HMDB ID HMDB14986
Secondary Accession Numbers None
Metabolite Identification
Common Name Levamisole
Description An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6)
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Dl-Tetramisol
  2. Dl-Tetramisole
  3. L-Tetramisole
  4. Levamisol [INN-Spanish]
  5. Levamisole hydrochloride
  6. Levamisolum [INN-Latin]
  7. Phenyl imidothiazole
Chemical Formula C11H12N2S
Average Molecular Weight 204.291
Monoisotopic Molecular Weight 204.072119084
IUPAC Name (6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
Traditional IUPAC Name levamisole
CAS Registry Number 14769-73-4
SMILES C1CN2C[C@@H](N=C2S1)C1=CC=CC=C1
InChI Identifier InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1
InChI Key HLFSDGLLUJUHTE-SNVBAGLBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Imidazothiazoles
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Imidazoline
  • Isothiourea
Direct Parent Imidazothiazoles
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Adjuvants, Immunologic
  • Antinematodal Agents
  • Antirheumatic Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 264 - 265 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.44e+00 g/L Not Available
LogP 2.3 Not Available
Predicted Properties
Property Value Source
LogP 2.20 ALOGPS
LogP 2.36 ChemAxon
LogS -2.15 ALOGPS
pKa (strongest basic) 6.98 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 15.6 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 60.08 ChemAxon
Polarizability 22.35 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00848
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00848
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00848 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 25037 Link_out
KEGG Compound ID C07070 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Levamisole Link_out
NuGOwiki Link HMDB14986 Link_out
Metagene Link HMDB14986 Link_out
METLIN ID Not Available
PubChem Compound 26879 Link_out
PDB ID Not Available
ChEBI ID 484948 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Van Belle H: Alkaline phosphatase. I. Kinetics and inhibition by levamisole of purified isoenzymes from humans. Clin Chem. 1976 Jul;22(7):972-6. Pubmed: 6169 Link_out
  2. Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology. Lancet. 1991 Jun 29;337(8757):1555-7. Pubmed: 1675705 Link_out
  3. Grishchenko SV, Lavrukhina LA, Ketiladze ES, Krylov VF, Ershov FI: [Results of combined therapy using levamisole for patients with influenza complicated by pneumonia]. Vopr Virusol. 1984 Mar-Apr;29(2):175-9. Pubmed: 6203228 Link_out

Enzymes
Name: Alkaline phosphatase, placental-like
Reactions: Not Available
Gene Name: ALPPL2
Uniprot ID: P10696 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA