Levamisole hydrochlorideProduct ingredient for Levamisole

Name
Levamisole hydrochloride
Drug Entry
Levamisole

Levamisole is an antihelminthic drug that was commonly used for the treatment of parasitic, viral, and bacterial infections. 4 It was manufactured by Janssen and first used in 1969 as an agent to treat worm infestations6 Levamisole was approved by the FDA in 1990 as an adjuvant treatment for colon cancer.7 Prior to this, levamisole was used as an antirheumatic therapy in the 1970s and 1980s for patients with rheumatoid arthritis.6

Because of its immunomodulatory effects, this drug has been studied in the treatment of various immune-mediated diseases, with some studies showing positive results. 4 This drug has also been used in combination with other drugs for the treatment of various cancers. 4,6

Levamisole was withdrawn from the American market in 2000 due to its ability to cause serious adverse effects, including agranulocytosis. 6 Interestingly, levamisole has been found as an adulterant in cocaine and can lead to a variety of adverse effects in individuals using this drug.5

Accession Number
DBSALT000822
Structure
Synonyms
Levamisole HCl
UNII
DL9055K809
CAS Number
16595-80-5
Weight
Average: 240.752
Monoisotopic: 240.048796823
Chemical Formula
C11H13ClN2S
InChI Key
LAZPBGZRMVRFKY-HNCPQSOCSA-N
InChI
InChI=1S/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H/t10-;/m1./s1
IUPAC Name
(6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole hydrochloride
SMILES
Cl.[H][C@@]1(CN2CCSC2=N1)C1=CC=CC=C1
KEGG Compound
C07906
PubChem Compound
27944
ChemSpider
25996
ChEBI
6433
ChEMBL
CHEMBL1770
Wikipedia
Levamisole
Predicted Properties
PropertyValueSource
Water Solubility1.44 mg/mLALOGPS
logP2.2ALOGPS
logP2.36Chemaxon
logS-2.2ALOGPS
pKa (Strongest Basic)6.98Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area15.6 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity60.08 m3·mol-1Chemaxon
Polarizability22.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon