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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:32:43 UTC
HMDB IDHMDB14986
Secondary Accession NumbersNone
Metabolite Identification
Common NameLevamisole
DescriptionAn 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
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 FormulaC11H12N2S
Average Molecular Weight204.291
Monoisotopic Molecular Weight204.072119084
IUPAC Name(6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
Traditional IUPAC Namelevamisole
CAS Registry Number14769-73-4
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 KeyHLFSDGLLUJUHTE-SNVBAGLBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassImidazothiazoles
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Imidazoline
  • Isothiourea
Direct ParentImidazothiazoles
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Adjuvants, Immunologic
  • Antinematodal Agents
  • Antirheumatic Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point264 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.44e+00 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP2.2ALOGPS
logP2.36ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)6.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.6ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.08ChemAxon
Polarizability22.35ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00848
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00848
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00848
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID25037
KEGG Compound IDC07070
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevamisole
NuGOwiki LinkHMDB14986
Metagene LinkHMDB14986
METLIN IDNot Available
PubChem Compound26879
PDB IDNot Available
ChEBI ID484948
References
Synthesis ReferenceNot 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
  2. Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology. Lancet. 1991 Jun 29;337(8757):1555-7. Pubmed: 1675705
  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

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
References
  1. Chang YL, Stanford CM, Keller JC: Calcium and phosphate supplementation promotes bone cell mineralization: implications for hydroxyapatite (HA)-enhanced bone formation. J Biomed Mater Res. 2000 Nov;52(2):270-8. Pubmed: 10951365
  2. Funk CJ: Alkaline phosphatase activity in whitefly salivary glands and saliva. Arch Insect Biochem Physiol. 2001 Apr;46(4):165-74. Pubmed: 11304750
  3. de Aguiar Matos JA, Borges FP, Tasca T, Bogo MR, De Carli GA, da Graca Fauth M, Dias RD, Bonan CD: Characterisation of an ATP diphosphohydrolase (Apyrase, EC 3.6.1.5) activity in Trichomonas vaginalis. Int J Parasitol. 2001 Jun;31(8):770-5. Pubmed: 11403767
  4. McDougall K, Plumb C, King WA, Hahnel A: Inhibitor profiles of alkaline phosphatases in bovine preattachment embryos and adult tissues. J Histochem Cytochem. 2002 Mar;50(3):415-22. Pubmed: 11850443
  5. Soory M, Suchak A: Effects of alkaline phosphatase and its inhibitor levamisole on the modulation of androgen metabolism by nicotine and minocycline in human gingival and oral periosteal fibroblasts. Arch Oral Biol. 2003 Jan;48(1):69-76. Pubmed: 12615144
  6. Mota A, Silva P, Neves D, Lemos C, Calhau C, Torres D, Martel F, Fraga H, Ribeiro L, Alcada MN, Pinho MJ, Negrao MR, Pedrosa R, Guerreiro S, Guimaraes JT, Azevedo I, Martins MJ: Characterization of rat heart alkaline phosphatase isoenzymes and modulation of activity. Braz J Med Biol Res. 2008 Jul;41(7):600-9. Pubmed: 18719742