(6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole

• ChemBase ID: 726
• Molecular Formular: C11H12N2S
• Molecular Mass: 204.29138
• Monoisotopic Mass: 204.07211939
• SMILES: S1C2=N[C@H](CN2CC1)c1ccccc1
• Canonical SMILES: C1CN2C(=N[C@H](C2)c2ccccc2)S1
• InChI: 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
• InChIKey: HLFSDGLLUJUHTE-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
• IUPAC Traditional name: levamisole; levamisole hydrochloride
• Brand Name: Ergamisol; Ketrax; LEVOMYSOL; Lepuron; Levamisol; Nilverm base; Tetramisol; Tetramisole; Tramisol; Vermisol 150; Wormicid
• Synonyms: (6S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazole Hydrochloride; (-)-Levamisole Hydrochloride; Ascaridil; Decaris; Dekaris; Ergamisol; Ergamisole; Meglum; NSC 177023; Nemicide; R 12654; Ripercol L; Solaskil; Spartakon L; Tramisol; Tramisole; l-Tetramisole Hydrochloride; Levamisole Hydrochloride; Levamisol [INN-Spanish]; L-Tetramisole; dl-Tetramisol; dl-Tetramisole; Phenyl imidothiazole; Levamisolum [INN-Latin]; Levamisole hydrochloride; Levamisole

Database IDs

• CAS Number: 16595-80-5; 14769-73-4
• PubChem SID: 160964189; 46509052
• PubChem CID: 26879
• ATC CODE: P02CE01; QP52AE01
• CHEMBL: 1454
• Chemspider ID: 25037
• DrugBank ID: DB00848
• KEGG ID: D08114
• Unique Ingredient Identifier: 2880D3468G
• Wikipedia Title: Levamisole
• Medline Plus: a697011

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.91581506
• LogD (pH = 7.4): 2.220205
• Log P: 2.358227
• Molar Refractivity: 60.0784 cm^3
• Polarizability: 23.02744 Å^3
• Polar Surface Area: 15.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -2.15
• Solubility (Water): 1.44e+00 g/l

PROPERTIES

Physical Property

• Solubility: 210 mg/mL; Methanol; Water
• Apperance: White Solid
• Melting Point: 223-225°C; 60°C (140°F)
• Density: 1.31 g/cm^3
• Hydrophobicity(logP): 2.3

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 4.4-5.6 hours (biphasic)
• Metabolism: Hepatic

DETAILS

DrugBank - DB00848

• 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: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - L331100

Biological response modifier with anthelmintic activity. Anthelmintic (nematodes); immunomodulator.

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
• Bullock, M.W., et al.: J. Med. Chem., 11, 169 (1966)
• Miller, M.J., et al.: Drugs, 20, 122 (1966)
• Stevenson, H.C., et al.: J. Clin. Oncol., 9, 2052 (1966)
• Amery, W.K., et al.: Int. J. Immunopharmacol., 1
• Thienpoint, D., et al.: Nature, 209, 1084 (1966)