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

• ChemBase ID: 93
• Molecular Formular: C14H14ClNS
• Molecular Mass: 263.78566
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2-chlorophenyl)methyl]-4H,5H,6H,7H-thieno[3,2-c]pyridine
• IUPAC Traditional name: ticlopidine
• Brand Name: Ticlid
• Synonyms: Ticlopidine HCL; Ticlopidine Hydrochloride; Ticlopidine

Database IDs

• CAS Number: 55142-85-3
• PubChem SID: 46504438; 160963556
• PubChem CID: 5472
• CHEBI ID: 9588
• ATC CODE: B01AC05
• CHEMBL: 833
• Chemspider ID: 5273
• DrugBank ID: DB00208
• KEGG ID: D08594
• Unique Ingredient Identifier: OM90ZUW7M1
• Wikipedia Title: Ticlopidine
• Medline Plus: a695036

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.3920543
• LogD (pH = 7.4): 3.93956
• Log P: 4.1959305
• Molar Refractivity: 74.328 cm^3
• Polarizability: 28.51201 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.25
• LOG S: -4.08
• Solubility (Water): 2.19e-02 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble
• Hydrophobicity(logP): 2.9

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: >80%
• Excretion: Renal and fecal
• Half Life: *12 hours (single dose)
• Metabolism: Hepatic
• Protein Bound: 98%
• Pregnancy Category: B1 (Australia); C (US)

DETAILS

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