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55142-85-3 molecular structure
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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 and InChIs

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

Cite this record

CBID:93 http://www.chembase.cn/molecule-93.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 2.3920543  LogD (pH = 7.4) 3.93956 
Log P 4.1959305  Molar Refractivity 74.328 cm3
Polarizability 28.51201 Å3 Polar Surface Area 3.24 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.25  LOG S -4.08 
Solubility (Water) 2.19e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
Freely soluble expand Show data source
Hydrophobicity(logP)
2.9 expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
>80% expand Show data source
Excretion
Renal and fecal expand Show data source
Half Life
*12 hours (single dose) expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
98% expand Show data source
Pregnancy Category
B1 (Australia) expand Show data source
C (US) expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia DrugBank DrugBank
DrugBank - DB00208 external link
Item Information
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

REFERENCES

REFERENCES

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