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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:46 UTC
HMDB IDHMDB0014986
Secondary Accession Numbers
  • HMDB14986
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
ValueSource
(-)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazoleChEBI
(-)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazoleChEBI
(-)-TetramisoleChEBI
(S)-(-)-LevamisoleChEBI
(S)-(-)-TetramisoleChEBI
(S)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]ThiazoleChEBI
KetraxChEBI
LepuronChEBI
LevamisolChEBI
LevamisolumChEBI
LevomysolChEBI
LevovermaxChEBI
TotalonChEBI
WormicidChEBI
DL-TetramisolHMDB
DL-TetramisoleHMDB
L-TetramisoleHMDB
Levamisole hydrochlorideHMDB
Phenyl imidothiazoleHMDB
DecarisMeSH
DekarisMeSH
Hydrochloride, levamisoleMeSH
LevotetramisoleMeSH
SolaskilMeSH
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 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
DescriptionThis compound belongs to the class of organic compounds known as imidazothiazoles. These are organic polycyclic compounds containing an imidazole ring fused to a thiazole ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Thiazole is a 6-membered ring that contains both sulfur and nitrogen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazothiazoles
Sub ClassNot Available
Direct ParentImidazothiazoles
Alternative Parents
Substituents
  • Imidazothiazole
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • 2-imidazoline
  • Isothiourea
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole (CHEBI:6432 )
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point264 - 265 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.44 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 Area15.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.08 m³·mol⁻¹ChemAxon
Polarizability22.35 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0090000000-3287b9f97484db3f8259View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0290000000-2a8784dae8e131756f29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-0930000000-975ff964afb959f70b6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-a8c5505d0b7fdeaf0370View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00o0-0900000000-80c580945e5a7ddd9141View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-056r-0930000000-d376a4d6ffa974193618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-d856a825b29504cf56b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-29757710d68d19c20f76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0190000000-e4e9e3b226281380147bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a6r-0980000000-ac1adb2c160be1dafe12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-056r-1920000000-4c40f20cc8cba971e7f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00bc-2900000000-9a1379a30cf72af41c53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-7b7b26cae9b220d1caabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0090000000-1bbcf954ce60d0b1fcaaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0190000000-07d289ec95e677a1b3aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a6r-0890000000-c2231044d3a23c9eb270View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-056r-1920000000-0a9caf1aaab83df71159View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00bc-2900000000-46aebcf766e13a170e5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0920000000-eed44b98c34d9c4e1c34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00848 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00848 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
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. Authors unspecified: 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 ]