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Levamisole

Catalog No. DB00848 Name DrugBank
CAS Number 14769-73-4 Website http://www.ualberta.ca/
M. F. C11H12N2S Telephone (780) 492-3111
M. W. 204.29138 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 726

SYNONYMS

IUPAC name
(6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
IUPAC Traditional name
levamisole
Brand Name
Wormicid
Lepuron
LEVOMYSOL
Tetramisol
Ergamisol
Levamisol
Nilverm base
Tetramisole
Tramisol
Ketrax
Vermisol 150
Synonyms
Phenyl imidothiazole
dl-Tetramisol
Levamisol [INN-Spanish]
L-Tetramisole
Levamisolum [INN-Latin]
Levamisole hydrochloride
dl-Tetramisole

DATABASE IDS

CAS Number 14769-73-4
PubChem SID 46509052
PubChem CID 26879

PROPERTIES

Hydrophobicity(logP) 2.3
Solubility 210 mg/mL

DETAILS

Description (English)
Item Information
Drug Groups approved
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)
Indication For adjuvant treatment in combination with fluorouracil after surgical resection in patients with Dukes' stage C colon cancer. Also used to treat malignant melanoma and head/neck cancer.
Levamisole was originally used as an antihelminthic to treat worm infestations in both humans and animals.
Pharmacology Levamisole is a synthetic imidazothiazole derivative that has been widely used in treatment of worm infestations in both humans and animals. As an anthelmintic, it probably works by targeting the nematode nicotinergic acetylcholine receptor. As an immunomodulator, it appears that Levamisole is an immunostimulant which has been shown to increase NK cells and activated T-cells in patients receiving this adjuvantly along with 5FU for Stage III colon cancer.
Toxicity LD50 = 40 mg/kg (Pigs, subcutaneous); LD50 = 180 mg/kg (rat, oral)
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic (extensive) with both active and inactive metabolites.
Absorption Levamisole is rapidly absorbed (2 hours) from the gastrointestinal tract.
Half Life 4.4-5.6 hours (biphasic)
Protein Binding 20-25%
References
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]
Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology. Lancet. 1991 Jun 29;337(8757):1555-7. [Pubmed]
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]
External Links
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REFERENCES

  • 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
  • Levamisole for corticosteroid-dependent nephrotic syndrome in childhood. British Association for Paediatric Nephrology. Lancet. 1991 Jun 29;337(8757):1555-7. Pubmed
  • 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