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Details

Stereochemistry ACHIRAL
Molecular Formula C14H14ClNS
Molecular Weight 263.786
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TICLOPIDINE

SMILES

ClC1=CC=CC=C1CN2CCC3=C(C2)C=CS3

InChI

InChIKey=PHWBOXQYWZNQIN-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H14ClNS
Molecular Weight 263.786
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Ticlopidine (trade name Ticlid) is an antiplatelet drug in the thienopyridine family which is an adenosine diphosphate (ADP) receptor inhibitor. Ticlopidine is a prodrug that is metabolized to an as yet undetermined metabolite that acts as a platelet aggregation inhibitor. Inhibition of platelet aggregation causes a prolongation of bleeding time. In its prodrug form, ticlopidine has no significance in vitro activity at the concentrations attained in vivo. The active metabolite of ticlopidine prevents binding of adenosine diphosphate (ADP) to its platelet receptor, impairing the ADP-mediated activation of the glycoprotein GPIIb/IIIa complex. It is proposed that the inhibition involves a defect in the mobilization from the storage sites of the platelet granules to the outer membrane. No direct interference occurs with the GPIIb/IIIa receptor. As the glycoprotein GPIIb/IIIa complex is the major receptor for fibrinogen, its impaired activation prevents fibrinogen binding to platelets and inhibits platelet aggregation. Ticlopidine is FDA approved for the prevention of strokes and, when combined with aspirin, for patients with a new coronary stent to prevent closure. There are also several off-label uses, including acute treatment of myocardial infarction and unstable angina, peripheral vascular disease, prevention of myocardial infarctions, diabetic retinopathy, and sickle cell disease. The most serious side effects associated with ticlopidine are those that affect the blood cells, although these life-threatening complications are relatively rare.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Drug-induced thrombotic microangiopathy: incidence, prevention and management.
2001
Indobufen: an updated review of its use in the management of atherothrombosis.
2001
Current oral antiplatelet agents to prevent atherothrombosis.
2001
Benefit of ADP receptor antagonists in atherothrombotic patients: new evidence.
2001
The use of antiplatelet agents in acute cardiac care.
2001 Apr
Clinical application of procedural platelet monitoring during percutaneous coronary intervention among patients at increased bleeding risk.
2001 Apr
Aspirin in patients with coronary artery disease: is it simply irresistible?
2001 Apr
Relative contributions of CYP2C9 and 2C19 to phenytoin 4-hydroxylation in vitro: inhibition by sulfaphenazole, omeprazole, and ticlopidine.
2001 Apr
[Treatment for recurrent paradoxical brain embolism through the patent foramen ovale].
2001 Apr
Drug-induced cholestasis.
2001 Apr
CURE--clopidogrel's major advance.
2001 Apr
[Optimal platelet inhibition therapy in unstable angina pectoris and after coronary interventions].
2001 Apr
[Pathophysiology of platelet activation and pharmacology of GPIIb/IIIa inhibitors].
2001 Apr
Regular or "super-aspirins"? A review of thienopyridines or aspirin to prevent stroke.
2001 Apr
Extracorporeal shockwave lithotripsy in patients treated with antithrombotic agents.
2001 Apr
[Pressure wire guide provisional coronary stent implantation].
2001 Apr
Long-term effects of intracoronary beta-radiation in balloon- and stent-injured porcine coronary arteries.
2001 Apr 24
Oral anticoagulant therapy during and after coronary angioplasty the intensity and duration of anticoagulation are essential to reduce thrombotic complications.
2001 Apr 24
[Acute heart attacks. Prognosis can be further improved].
2001 Apr 5
Role of transforming growth factor beta1 in microvascular endothelial cell apoptosis associated with thrombotic thrombocytopenic purpura and hemolytic-uremic syndrome.
2001 Jan
[Early hepatopathy induced by ticlopidine].
2001 Jan
Comparison of ticlopidine and cilostazol for the prevention of restenosis after percutaneous transluminal coronary angioplasty.
2001 Jan
The role of adenosine 5'-diphosphate receptor blockade in patients with cardiovascular disease.
2001 Jul
Extensive thrombus prior to elective percutaneous coronary intervention.
2001 Jul
Diffuse alveolar hemorrhage after clopidogrel use.
2001 Jul
[Toxic skin reaction to clopidogrel].
2001 Jun
Low-pressure deployment of stents: short- and long-term outcome.
2001 Jun
Molecular identification and characterization of the platelet ADP receptor targeted by thienopyridine antithrombotic drugs.
2001 Jun
Ticlopidine-induced interstitial pulmonary disease: a case report.
2001 Jun
Acute and mid-term results of phosphorylcholine-coated stents in primary coronary stenting for acute myocardial infarction.
2001 Jun
Comparative trial of stent-like balloon angioplasty versus coronary stenting for acute myocardial infarction.
2001 Jun
Clinical correlates and drug treatment of residents with stroke in long-term care.
2001 Jun
Ticlopidine monotherapy following coronary stent deployment: "penny wise and pound foolish".
2001 Jun
Efficacy and safety of ticlopidine monotherapy versus ticlopidine and aspirin after coronary artery stenting: follow-up results of a randomized study.
2001 Jun
Incidence of thrombotic occlusion and major adverse cardiac events between two and four weeks after coronary stent placement: analysis of 5,678 patients with a four-week ticlopidine regimen.
2001 Jun 15
Stenting of partial and total coronary occlusions in Trinidad and Tobago.
2001 Mar
Platelet aggregation inhibition with ticlopidine in the treatment of stroke.
2001 Mar
[Acute coronary syndromes: an update. I. Pathogenesis and drug therapy].
2001 Mar
[Acute coronary syndromes: an update. II. Coronary revascularization and risk stratification].
2001 Mar
[Pharmacy clinics. Medication of the month. Clopidogrel (Plavix)].
2001 Mar
Thrombotic thrombocytopenic purpura--a syndrome caused by multiple pathogenetic mechanisms.
2001 May
Cardiovascular drug-drug interactions.
2001 May
[Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery].
2001 May
The inhibition of oxygen radical release from human neutrophils by resting platelets is reversed by administration of acetylsalicylic acid or clopidogrel.
2001 May
Effect of cilostazol on restenosis after coronary angioplasty and stenting in comparison to conventional coronary artery stenting with ticlopidine.
2001 May
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines.
2001 May
Edge stenosis after intracoronary radiotherapy: angiographic, intravascular, and histological findings.
2001 May 1
Prolonged antiplatelet therapy to prevent late thrombosis after intracoronary gamma-radiation in patients with in-stent restenosis: Washington Radiation for In-Stent Restenosis Trial plus 6 months of clopidogrel (WRIST PLUS).
2001 May 15
P2y(12), a new platelet ADP receptor, target of clopidogrel.
2001 May 4
Clopidogrel and aplastic anaemia.
2001 May 5
Patents

Sample Use Guides

In Vivo Use Guide
250 mg PO q12hr with food
Route of Administration: Oral
In Vitro Use Guide
Following preparation of the platelet concentrate, 1.2 mL of ThromboSol was added to some units (treated units) through a sterile port. We then resuspended the treated PC by gentle massaging and directly placed it at 4°C without shaking. The resulting treated PC contained the following reagents: amiloride (0.25 mM), adenosine (0.1 mM), SNP (50 mkM), dipyridamole (40 mkM) Ticlopidine (0.75 mkM), and quinacrine (0.2 mkM). In parallel, platelet concentrate were stored as control units at 22°C with shaking or at 4°C without shaking. After storage, aliquots of control and treated platelet concentrate were harvested for analysis as follows. The platelet concentrate to be sampled was gently massaged to achieve a homogenous cell suspension, and, by using a syringe with an 18-gauge needle, a 3-mL sample of platelets was removed via the sterile port. We then placed the platelet sample in a 15-mL polypropylene conical tube and centrifuged it at 950 x g for 20 minutes at 22°C to remove the ThromboSol. The resulting platelet pellet was resuspended to the original sample volume with autologous platelet-poor plasma (PPP) and the platelet count was determined with a hematology analyzer
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:27:54 UTC 2019
Edited
by admin
on Tue Oct 22 00:27:54 UTC 2019
Record UNII
OM90ZUW7M1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TICLOPIDINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TICLOPIDINE [MI]
Common Name English
TICLOPIDINE [WHO-DD]
Common Name English
TICLOPIDINE [VANDF]
Common Name English
TICLOPIDINE [INN]
Common Name English
TICLOPIDIN-PUREN
Brand Name English
Classification Tree Code System Code
NDF-RT N0000175578
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
NCI_THESAURUS C80483
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
LIVERTOX 963
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
NDF-RT N0000008832
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
WHO-ATC B01AC05
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
NDF-RT N0000008832
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
WHO-VATC QB01AC05
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
Code System Code Type Description
EPA CompTox
55142-85-3
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
CAS
55142-85-3
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
WIKIPEDIA
TICLOPIDINE
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
IUPHAR
7307
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
RXCUI
10594
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY RxNorm
MESH
D013988
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
ECHA (EC/EINECS)
259-498-5
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
PUBCHEM
5472
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
MERCK INDEX
M10855
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C61972
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
EVMPD
SUB11028MIG
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
ChEMBL
CHEMBL833
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
DRUG BANK
DB00208
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
INN
3908
Created by admin on Tue Oct 22 00:27:54 UTC 2019 , Edited by admin on Tue Oct 22 00:27:54 UTC 2019
PRIMARY
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SALT/SOLVATE -> PARENT
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