5-[(2-chlorophenyl)methyl]-4H,5H,6H,7H-thieno[3,2-c]pyridine

• ChemBase编号: 93
• 分子式: C14H14ClNS
• 平均质量: 263.78566
• 单一同位素质量: 263.05354813
• SMILES: Clc1c(CN2CCc3sccc3C2)cccc1
• Canonical SMILES: Clc1ccccc1CN1CCc2c(C1)ccs2
• InChI: InChI=1S/C14H14ClNS/c15-13-4-2-1-3-11(13)9-16-7-5-14-12(10-16)6-8-17-14/h1-4,6,8H,5,7,9-10H2
• InChIKey: PHWBOXQYWZNQIN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-[(2-chlorophenyl)methyl]-4H,5H,6H,7H-thieno[3,2-c]pyridine
• IUPAC传统名: ticlopidine
• 商标名: Ticlid
• 别名: Ticlopidine HCL; Ticlopidine Hydrochloride; Ticlopidine

登记号

• CAS号: 55142-85-3
• PubChem SID: 46504438; 160963556
• PubChem CID: 5472
• CHEBI ID: 9588
• ATC码: B01AC05
• CHEMBL: 833
• Chemspider ID: 5273
• DrugBank ID: DB00208
• KEGG ID: D08594
• 美国药典/FDA物质标识码: OM90ZUW7M1
• 维基百科标题: Ticlopidine
• Medline Plus: a695036

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 2.3920543
• LogD (pH = 7.4): 3.93956
• Log P: 4.1959305
• 摩尔折射率: 74.328 cm^3
• 极化性: 28.51201 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.25
• LOG S: -4.08
• 溶解度: 2.19e-02 g/l

分子性质

理化性质

• 溶解度: Freely soluble
• 疏水性(logP): 2.9

药理学性质

• 给药途径: Oral
• 生物利用度: >80%
• 排泄: Renal and fecal
• 半衰期: *12 hours (single dose)
• 代谢: Hepatic
• 蛋白结合率: 98%
• 妊娠期药物分类: B1 (Australia); C (US)

详细说明

DrugBank - DB00208

• Drug Groups: approved
• Description: Ticlopidine is an effective inhibitor of platelet aggregation. The drug has been found to significantly reduce infarction size in acute myocardial infarcts and is an effective antithrombotic agent in arteriovenous fistulas, aorto-coronary bypass grafts, ischemic heart disease, venous thrombosis, and arteriosclerosis. [PubChem]
• Indication: Used to reduce the risk of thrombotic stroke (fatal or nonfatal) in patients who have experienced stroke precursors, and in patients who have had a completed thrombotic stroke.
• Pharmacology: Ticlopidine is a platelet aggregation inhibitor structurally and pharmacologically similar to clopidogrel. When taken orally, ticlopidine causes a time- and dose-dependent inhibition of both platelet aggregation and release of platelet granule constituents, as well as a prolongation of bleeding time. The intact drug has no significant in vitro activity at the concentrations attained in vivo; and, although analysis of urine and plasma indicates at least 20 metabolites, no metabolite which accounts for the activity of ticlopidine has been isolated.
• Toxicity: Single oral doses of ticlopidine at 1600 mg/kg and 500 mg/kg were lethal to rats and mice, respectively. Symptoms of acute toxicity were GI hemorrhage, convulsions, hypothermia, dyspnea, loss of equilibrium and abnormal gait.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized extensively by the liver; only trace amounts of intact drug are detected in the urine. At least 20 metabolites have been identified. It has been proposed that 1 or more active metabolites may account for ticlopidine's activity, because ticlopidine itself is an extremely weak platelet aggregation inhibitor in vitro at the concentrations achieved in vivo. However, no active metabolite has been identified.
• Absorption: Absorption is greater than 80%. Food increases absorption.
• Half Life: Half-life following a single 250-mg dose is approximately 7.9 hours in subjects 20 to 43 years of age and 12.6 hours in subjects 65 to 76 years of age. With repeated dosing (250 mg twice a day), half-life is about 4 days in subjects 20 to 43 years of age and about 5 days in subjects 65 to 76 years of age.
• Protein Binding: Binds reversibly (98%) to plasma proteins, mainly to serum albumin and lipoproteins. The binding to albumin and lipoproteins is nonsaturable over a wide concentration range. Ticlopidine also binds to alpha-1 acid glycoprotein. At concentrations attained with the recommended dose, only 15% or less ticlopidine in plasma is bound to this protein.
• Elimination: Ticlopidine hydrochloride is metabolized extensively by the liver; only trace amounts of intact drug are detected in the urine. Approximately 1/3 of the dose excreted in the feces is intact ticlopidine hydrochloride, possibly excreted in the bile.
• External Links: Wikipedia; RxList; Drugs.com