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

• ChemBase编号: 726
• 分子式: C11H12N2S
• 平均质量: 204.29138
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazole
• IUPAC传统名: levamisole; levamisole hydrochloride
• 商标名: Ergamisol; Ketrax; LEVOMYSOL; Lepuron; Levamisol; Nilverm base; Tetramisol; Tetramisole; Tramisol; Vermisol 150; Wormicid
• 别名: (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

登记号

• CAS号: 16595-80-5; 14769-73-4
• PubChem SID: 160964189; 46509052
• PubChem CID: 26879
• ATC码: QP52AE01; P02CE01
• CHEMBL: 1454
• Chemspider ID: 25037
• DrugBank ID: DB00848
• KEGG ID: D08114
• 美国药典/FDA物质标识码: 2880D3468G
• 维基百科标题: Levamisole
• Medline Plus: a697011

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.91581506
• LogD (pH = 7.4): 2.220205
• Log P: 2.358227
• 摩尔折射率: 60.0784 cm^3
• 极化性: 23.02744 Å^3
• 极化表面积: 15.6 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -2.15
• 溶解度: 1.44e+00 g/l

分子性质

理化性质

• 溶解度: 210 mg/mL; Methanol; Water
• 外观: White Solid
• 熔点: 223-225°C; 60°C (140°F)
• 密度: 1.31 g/cm^3
• 疏水性(logP): 2.3

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

药理学性质

• 给药途径: Oral
• 半衰期: 4.4-5.6 hours (biphasic)
• 代谢: Hepatic

详细说明

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.

参考文献

• 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)