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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H36N2O5S.ClH.H2O
Molecular Weight 495.073
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIROFIBAN HYDROCHLORIDE

SMILES

O.Cl.CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O

InChI

InChIKey=HWAAPJPFZPHHBC-FGJQBABTSA-N
InChI=1S/C22H36N2O5S.ClH.H2O/c1-2-3-16-30(27,28)24-21(22(25)26)17-19-7-9-20(10-8-19)29-15-5-4-6-18-11-13-23-14-12-18;;/h7-10,18,21,23-24H,2-6,11-17H2,1H3,(H,25,26);1H;1H2/t21-;;/m0../s1

HIDE SMILES / InChI

Description

Tirofiban is a non-peptide antagonist of the platelet glycoprotein (GP) IIb/IIIa receptor. Tirofiban is a reversible, competitive inhibitor of GP IIb/IIIa receptors, exerting its effects via the prevention of the binding of fibrinogen and other ligands, resulting in the inhibition of the last common step of thrombi formation. Tirofiban was discovered by Merck, USA, and was approved by the FDA in 1998 under the trade name AGGRASTAT. AGGRASTAT, in combination with heparin, is indicated for the treatment of acute coronary syndrome, including patients who are to be managed medically and those undergoing percutaneous transluminal coronary angioplasty or atherectomy. AGGRASTAT reduces the risk of ischaemic complications in patients with unstable angina/non-Q-wave myocardial infarction and high-risk patients undergoing revascularisation when used against a background of heparin and aspirin. Furthermore, the drug has an acceptable tolerability profile. Therefore, intravenous tirofiban is likely to be used as an adjunct to heparin and aspirin in patients with acute coronary syndromes including high-risk patients undergoing revascularisation.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
15.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AGGRASTAT

AUC

ValueDoseCo-administeredAnalytePopulation
193.4 ng × h/mL
0.15 μg/kg/min other, intravenous
TIROFIBAN plasma
Homo sapiens
209.5 ng × h/mL
0.2 μg/kg/min other, intravenous
TIROFIBAN plasma
Homo sapiens
92.5 ng × h/mL
0.1 μg/kg/min other, intravenous
TIROFIBAN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
0.15 μg/kg/min other, intravenous
TIROFIBAN plasma
Homo sapiens
1.1 h
0.2 μg/kg/min other, intravenous
TIROFIBAN plasma
Homo sapiens
2 h
0.1 μg/kg/min other, intravenous
TIROFIBAN plasma
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
In most patients, AGGRASTAT should be administered intravenously, at an initial rate of 0.4 µg/kg/min for 30 minutes and then continued at 0.1 µg/kg/min. Patients with severe renal insufficiency (creatinine clearance <30 mL/min) should receive half the usual rate of infusion.
Route of Administration: Intravenous
In Vitro Use Guide
Platelet-rich plasma from each subject was incubated in vitro with increasing concentrations of tirofiban (25, 37.5, and 50ng/ml), patients with moderate to severe renal dysfunction suppress their platelet aggregation to <10% with 25ng/ml of tirofiban, one-third of the standard effective dose for patients with normal renal function.