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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 of TICLOPIDINE

SMILES

ClC1=C(CN2CCC3=C(C2)C=CS3)C=CC=C1

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
TICLID
Preventing
TICLID

Cmax

ValueDoseCo-administeredAnalytePopulation
365.3 ng/mL
250 mg single, oral
TICLOPIDINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1053.9 ng × h/mL
250 mg single, oral
TICLOPIDINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.46 h
250 mg single, oral
TICLOPIDINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
TICLOPIDINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
OM90ZUW7M1
Record Status Validated (UNII)
Record Version