TICLOPIDINE

Details

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

SHOW SMILES / InChI

Structure Search

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/19-979S018_Ticlid_prntlbl.pdf

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

Targets

Primary Target	Pharmacology	Condition	Potency
platelet aggregation 80 Target ID: GO:0070527 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/19-979S018_Ticlid_prntlbl.pdf	Inhibitor 8504
Purinergic receptor P2Y12 23 Target ID: CHEMBL2001 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15852221	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thrombotic stroke 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/19-979S018_Ticlid_prntlbl.pdf	Preventing		Approved 8583	TICLID Approved Use Ticlopidine hydrochloride tablets are indicated: 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. Because ticlopidine is associated with a risk of life-threatening blood dyscrasias including thrombotic thrombocytopenic purpura (TTP), neutropenia/agranulocytosis and aplastic anemia (see BOX WARNING and WARNINGS ), ticlopidine should be reserved for patients who are intolerant or allergic to aspirin therapy or who have failed aspirin therapy. as adjunctive therapy with aspirin to reduce the incidence of subacute stent thrombosis in patients undergoing successful coronary stent implantation (see CLINICAL TRIALS ). Launch Date 1991
Coronary artery disease 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/19-979S018_Ticlid_prntlbl.pdf	Preventing		Approved 8583	TICLID Approved Use Ticlopidine hydrochloride tablets are indicated: 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. Because ticlopidine is associated with a risk of life-threatening blood dyscrasias including thrombotic thrombocytopenic purpura (TTP), neutropenia/agranulocytosis and aplastic anemia (see BOX WARNING and WARNINGS ), ticlopidine should be reserved for patients who are intolerant or allergic to aspirin therapy or who have failed aspirin therapy. as adjunctive therapy with aspirin to reduce the incidence of subacute stent thrombosis in patients undergoing successful coronary stent implantation (see CLINICAL TRIALS ). Launch Date 1991

C_max

Value	Dose	Co-administered	Analyte	Population
365.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12419644	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		TICLOPIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
1053.9 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12419644	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		TICLOPIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.46 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12419644	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		TICLOPIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/anda/99/75161_Ticlopidine%20Hydrochloride_Prntlbl.pdf			TICLOPIDINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
200 mg 1 times / day multiple, oral Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18033957/	unhealthy, 64.7 Health Status: unhealthy Age Group: 64.7 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18033957/	Other AEs: Leukopenia, Neutropenia... Other AEs: Leukopenia (4 patients) Neutropenia (14 patients) Aspartate aminotransferase increased (13 patients) ALT increased (36 patients) Gamma GT increased (54 patients) ALP increased (2 patients) Cerebral hemorrhage (1 patient) Gastric ulcer hemorrhage (1 patient) Melena (1 patient) Epistaxis (2 patients) Rash (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18033957/
250 mg 2 times / day multiple, oral Recommended Dose: 250 mg, 2 times / day Route: oral Route: multiple Dose: 250 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20704700/	unhealthy, 70 Health Status: unhealthy Age Group: 70 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/20704700/	Disc. AE: Agranulocytosis, AST increased... AEs leading to discontinuation/dose reduction: Agranulocytosis (1 patient) AST increased (1 patient) ALT increased (1 patient) Gamma GT increased (1 patient) ALP increased (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20704700/
250 mg 2 times / day multiple, oral Recommended Dose: 250 mg, 2 times / day Route: oral Route: multiple Dose: 250 mg, 2 times / day Sources: https://pdf.hres.ca/dpd_pm/00015633.PDF	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pdf.hres.ca/dpd_pm/00015633.PDF	Disc. AE: Diarrhea, Nausea... AEs leading to discontinuation/dose reduction: Diarrhea (12.5%) Nausea (7%) Dyspepsia (7%) Rash (5.1%) GI pain (3.7%) Neutropenia (2.4%) Purpura (2.2%) Vomiting (1.9%) Flatulence (1.5%) Pruritus (1.3%) Dizziness (1.1%) Anorexia (1%) Sources: https://pdf.hres.ca/dpd_pm/00015633.PDF

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 CYP2E1 1060 CYP3A 227 CYP2B6 926	OATP2B1 122 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP3A5 446 CYP2J2 71 CES1 45

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10759690/	moderate [Ki 49 uM]
CYP3A 317	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10759690/	no [Ki >1000 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10759690/	unlikely [Ki 584 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9390115/ \| https://pubmed.ncbi.nlm.nih.gov/10759690/	weak [Ki 38.8 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10759690/	yes [Ki 3.4 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9390115/ \| https://pubmed.ncbi.nlm.nih.gov/10759690/ \| https://pubmed.ncbi.nlm.nih.gov/19845434/ \| https://pubmed.ncbi.nlm.nih.gov/11580286/	yes [Ki 3.7 uM]	yes (co-administration study) Comment: [PMID: 10759690]: Ki = 1.2 uM Sources: https://pubmed.ncbi.nlm.nih.gov/9390115/ \| https://pubmed.ncbi.nlm.nih.gov/10759690/ \| https://pubmed.ncbi.nlm.nih.gov/19845434/ \| https://pubmed.ncbi.nlm.nih.gov/11580286/
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19047469/ \| https://pubmed.ncbi.nlm.nih.gov/14563790/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	no
CYP2J2 71	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	no
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	no
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	yes
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24170778/	yes
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16707409/ \| https://pubmed.ncbi.nlm.nih.gov/28414144/	yes	yes (co-administration study) Comment: Coadministration with Ergoloid mesylates: AUC decreased 30.4% Sources: https://pubmed.ncbi.nlm.nih.gov/16707409/ \| https://pubmed.ncbi.nlm.nih.gov/28414144/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9588	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9588
ChemicalBook	CB7674370	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7674370
eMolecules	902580	https://www.emolecules.com/cgi-bin/more?vid=902580
MolPort	MolPort-002-507-849	https://www.molport.com/shop/molecule-link/MolPort-002-507-849
ZINC	ZINC000019594599	http://zinc15.docking.org/substances/ZINC000019594599

PubMed

Title	Date	PubMed
Indobufen: an updated review of its use in the management of atherothrombosis.	2001	11392445
Benefit of ADP receptor antagonists in atherothrombotic patients: new evidence.	2001	11316916
Cerebrovascular disease associated with marijuana abuse: a case report.	2001	11306781
Novel platelet inhibitors.	2001	11160773
The use of antiplatelet agents in acute cardiac care.	2001 Apr	11450321
Clinical application of procedural platelet monitoring during percutaneous coronary intervention among patients at increased bleeding risk.	2001 Apr	11406730
Aspirin in patients with coronary artery disease: is it simply irresistible?	2001 Apr	11406726
Short-term outcome of stent implantation in saphenous vein grafts: predictors of distal embolization and restenosis.	2001 Apr	11316120
Ticlopidine versus aspirin after myocardial infarction (STAMI) trial.	2001 Apr	11300432
Platelet and leukocyte deactivation after intracoronary stent placement in patients receiving combined antiplatelet therapy.	2001 Apr	11292188
Clinical and angiographical follow-up after implantation of a 6--12 microCi radioactive stent in patients with coronary artery disease.	2001 Apr	11286524
Results of CURE trial for acute coronary syndrome.	2001 Apr 11	11308379
Stent thrombosis in the modern era: a pooled analysis of multicenter coronary stent clinical trials.	2001 Apr 17	11306525
[Acute heart attacks. Prognosis can be further improved].	2001 Apr 5	11340908
Susac's syndrome: beneficial effects of corticosteroid therapy in a Japanese case.	2001 Feb	11300147
Newer antiplatelet therapies in stroke prevention.	2001 Feb	11280112
Antiplatelet therapy in the elderly. Aspirin, ticlopidine-clopidogrel, and GPIIb/GPIIIa antagonists.	2001 Feb	11270132
Thrombolysis and antithrombotic therapy for coronary artery disease.	2001 Feb	11270130
Antithrombotic and thrombolytic therapy for ischemic stroke.	2001 Feb	11270127
[Late stent thrombosis after intracoronary brachytherapy. A case report and review of the literature].	2001 Feb	11263004
Reduced incidence of clinical restenosis with newer generation stents, stent oversizing, and high-pressure deployment: single-operator experience.	2001 Feb	11214741
Protective effects of SM-20302, an orally active GPIIb/IIIa antagonist, in an ADP/epinephrine-induced guinea pig model of transient cerebral ischemia.	2001 Feb 1	11228335
Fatal aplastic anaemia associated with clopidogrel.	2001 Feb 10	11273071
[Update on the treatment with platelet antiaggregation agents].	2001 Jan	11291339
[Clopidogrel? Known or known?].	2001 Jan	11223636
[The new limitations of the Italian Regulatory Agency on Drugs].	2001 Jan	11216082
Stasis ulcers refractory to therapy--accelerated healing by treatment with clopidogrel +/- dalteparin: a preliminary report.	2001 Jan	11190899
Fixed drug eruption from ticlopidine, with positive lesional patch test.	2001 Jan	11156015
Angioplasty increases coronary sinus F2-isoprostane formation: evidence for in vivo oxidative stress during PTCA.	2001 Jan	11153776
[2 platelet inhibitors administered at the same time. Improved prognosis in myocardial infarct?]].	2001 Jan 11	11219401
Identification of the platelet ADP receptor targeted by antithrombotic drugs.	2001 Jan 11	11196645
Superiority of clopidogrel versus aspirin in patients with prior cardiac surgery.	2001 Jan 23	11157686
Febrile pancytopenia associated with clopidogrel.	2001 Jan 8	11146710
Clopidogrel (Plavix): hematological reactions.	2001 Jan 9	11202680
The role of adenosine 5'-diphosphate receptor blockade in patients with cardiovascular disease.	2001 Jul	11448660
Low-pressure deployment of stents: short- and long-term outcome.	2001 Jun	11428540
Ticlopidine-induced interstitial pulmonary disease: a case report.	2001 Jun	11399735
Stenting of partial and total coronary occlusions in Trinidad and Tobago.	2001 Mar	11398282
[Acute coronary syndromes: an update. II. Coronary revascularization and risk stratification].	2001 Mar	11349613
Activation of Gi-coupled receptors releases a tonic state of inhibited platelet aggregation.	2001 Mar	11297037
Platelet CD40 ligand (CD40L)--subcellular localization, regulation of expression, and inhibition by clopidogrel.	2001 Mar	11297035
Usefulness of intracoronary angioscopy for elucidating the cause of subacute thrombosis after stenting.	2001 Mar	11266200
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.	2001 Mar	11256484
Efficacy of heparin-coated stent in early setting of acute myocardial infarction.	2001 Mar	11246241
Acute and subacute stent occlusion; risk-reduction by ionic contrast media.	2001 Mar	11207080
Metabolic characterization of the major human small intestinal cytochrome p450s.	2001 Mar	11181505
Ticlopidine pretreatment before coronary stenting is associated with sustained decrease in adverse cardiac events: data from the Evaluation of Platelet IIb/IIIa Inhibitor for Stenting (EPISTENT) Trial.	2001 Mar 13	11245644
Thrombotic thrombocytopenic purpura--a syndrome caused by multiple pathogenetic mechanisms.	2001 May	11416985
Cardiovascular drug-drug interactions.	2001 May	11407107
New recommendations from the 1999 American College of Cardiology/American Heart Association acute myocardial infarction guidelines.	2001 May	11346067

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 `Mon Mar 31 18:07:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:09 GMT 2025`
Record UNII	OM90ZUW7M1
Record Status	`Validated (UNII)`
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Name

Type

Language

TICLOPIDIN-PUREN

Preferred Name

English

TICLOPIDINE

Official Name

English

TICLOPIDINE [MI]

Common Name

English

Ticlopidine [WHO-DD]

Common Name

English

TICLOPIDINE [VANDF]

Common Name

English

ticlopidine [INN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175578