U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H36N2O5S
Molecular Weight 440.597
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIROFIBAN

SMILES

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

InChI

InChIKey=COKMIXFXJJXBQG-NRFANRHFSA-N
InChI=1S/C22H36N2O5S/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)/t21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H36N2O5S
Molecular Weight 440.597
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19343166 | https://www.ncbi.nlm.nih.gov/pubmed/9878994

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
15.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AGGRASTAT

Approved Use

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. In this setting, AGGRASTAT has been shown to decrease the rate of a combined endpoint of death, new myocardial infarction or refractory ischemia/repeat cardiac procedure.

Launch Date

1998
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
193.4 ng × h/mL
0.15 μg/kg/min other, intravenous
dose: 0.15 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TIROFIBAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
209.5 ng × h/mL
0.2 μg/kg/min other, intravenous
dose: 0.2 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TIROFIBAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
92.5 ng × h/mL
0.1 μg/kg/min other, intravenous
dose: 0.1 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TIROFIBAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.6 h
0.15 μg/kg/min other, intravenous
dose: 0.15 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TIROFIBAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.1 h
0.2 μg/kg/min other, intravenous
dose: 0.2 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TIROFIBAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2 h
0.1 μg/kg/min other, intravenous
dose: 0.1 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TIROFIBAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim
PubMed

PubMed

TitleDatePubMed
Bleeding risk of tirofiban, a nonpeptide GPIIb/IIIa platelet receptor antagonist in progressive stroke: an open pilot study.
2001
Safety and efficacy of thrombolysis with alteplase (50 mg) plus tirofiban versus alteplase (100 mg) alone in acute myocardial infarction: preliminary findings.
2001 Aug
Platelet glycoprotein IIb/IIIa-receptor inhibitors in patients with acute coronary syndromes or undergoing percutaneous coronary interventions: a review.
2001 Aug
Estimation of anti-platelet drugs on human platelet aggregation with a novel whole blood aggregometer by a screen filtration pressure method.
2001 Aug
GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us.
2001 Dec
Cost implications of routine tirofiban use in the management of acute coronary syndromes.
2001 Dec
One-year experience with the platelet glycoprotein IIb/IIIa antagonist tirofiban and heparin during cardiopulmonary bypass in patients with heparin-induced thrombocytopenia type II.
2001 Dec
Perioperative use of tirofiban hydrochloride (Aggrastat) does not increase surgical bleeding after emergency or urgent coronary artery bypass grafting.
2001 Dec
Standardized ultrasound as a new method to induce platelet aggregation: evaluation, influence of lipoproteins and of glycoprotein IIb/IIIa antagonist tirofiban.
2001 Dec
A risk stratification scheme for selection of a glycoprotein IIb/IIIa inhibitor during percutaneous coronary intervention based on clinical and angiographic criteria.
2001 Dec 1
Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy.
2001 Dec 18
Glycoprotein IIb/IIIa receptor blockers in acute coronary syndromes.
2001 Dec 8
Augmentation of in-vitro clot dissolution by low frequency high-intensity ultrasound combined with antiplatelet and antithrombotic drugs.
2001 May
Elevation in serum troponin I predicts the benefit of tirofiban.
2001 May
Short-term comparative outcomes associated with the use of GP IIb/IIIa antagonists in patients undergoing coronary intervention.
2001 May
[Indications for intravenous GPIIb/IIIa receptor inhibitors in acute coronary syndrome without prolonged ST syndrome].
2001 Nov
Small peptide GP IIb/IIIa receptor inhibitors as upstream therapy in non-ST-segment elevation acute coronary syndromes: results of the PURSUIT, PRISM, PRISM-PLUS, TACTICS, and PARAGON trials.
2001 Nov
ESPRIT in context: pharmacology matters!
2001 Nov
[Rescue thrombectomy after stent implantation in a degenerating aortocoronary bypass].
2001 Nov 15
Comparison of early invasive and conservative strategies in patients with unstable coronary syndromes.
2001 Nov 22
Comparison of early invasive and conservative strategies in patients with unstable coronary syndromes.
2001 Nov 22
Intravenous glycoprotein IIb/IIIa inhibition in non-ST segment elevation acute coronary syndromes.
2001 Nov-Dec
Comparison of GP IIB/IIIA inhibitors and their activity as measured by aggregometry, flow cytometry, single platelet counting, and the rapid platelet function analyzer.
2001 Oct
Differential effects of citrate versus PPACK anticoagulation on measured platelet inhibition by abciximab, eptifibatide and tirofiban.
2001 Oct
[Comparison of 2 platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization].
2001 Oct
[Comparison of early invasive and conservative strategies in patients with unstable coronary syndromes treated with the glycoprotein IIb/IIIa inhibitor tirofiban].
2001 Oct
Increased reperfusion by glycoprotein IIb/IIIa receptor antagonist administration in case of unsuccessful and failed thrombolysis in patients with acute myocardial infarction: a pilot study.
2001 Oct
A comparison of total hospital costs for percutaneous coronary intervention patients receiving abciximab versus tirofiban.
2001 Oct
Stability of tirofiban hydrochloride in 0.9% sodium chloride injection for 30 days.
2001 Oct 1
Effects of clopidogrel pretreatment before percutaneous coronary intervention in patients treated with glycoprotein IIb/IIIa inhibitors (abciximab or tirofiban).
2001 Oct 15
Use of coronary revascularization in patients with unstable and non-ST-segment elevation acute myocardial infarction.
2001 Oct 18
Interpreting new treatment guidelines for non-ST-segment elevation acute coronary syndromes.
2001 Oct 18
[Comparison of two platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization].
2001 Sep
Should patients with unstable coronary syndromes routinely undergo cardiac catheterization and appropriate revascularization?
2001 Sep
ReoPro rules: results from the 'Do Tirofiban and ReoPro Give Similar Efficacy Trial' (TARGET).
2001 Sep
Resolution of a spontaneous coronary artery thrombus with a new antiplatelet agent.
2001 Sep
Alternatives to unfractionated heparin for anticoagulation in cardiopulmonary bypass.
2001 Sep
Pharmacodynamic characterization of the interaction between abciximab or tirofiban with unfractionated or a low molecular weight heparin in healthy subjects.
2001 Sep
Adjunctive therapies in the cath lab. Use of combination glycoprotein IIb/IIIa inhibitor and direct thrombin inhibitor drugs to support percutaneous coronary stent placement in a patient with renal insufficiency and heparin-induced thrombocytopenia.
2001 Sep
Adjunctive therapies in the cath lab. Intracoronary tirofiban infusion in a case with massive intracoronary thrombus.
2001 Sep
Adjunctive therapies in the cath lab. Combination of tirofiban and alteplase in acute myocardial infarction.
2001 Sep
Platelet glycoprotein inhibitors in patients with medically managed acute coronary syndrome: does the enthusiasm exceed the science?
2001 Sep
A risk score system for predicting adverse outcomes and magnitude of benefit with glycoprotein IIb/IIIa inhibitor therapy in patients with unstable angina pectoris.
2001 Sep 1
Differential inhibition of adenosine diphosphate- versus thrombin receptor-activating peptide-stimulated platelet fibrinogen binding by abciximab due to different glycoprotein IIb/IIIa activation kinetics.
2001 Sep 1
Dissociation of glycoprotein IIb/IIIa antagonists from platelets does not result in fibrinogen binding or platelet aggregation.
2001 Sep 18
Oral glycoprotein IIb/IIa antagonists for unstable angina--is there still a chance for the oral substances?
2001 Sep 30
The role of glycoprotein IIb/IIIa inhibition in the management of acute coronary syndromes.
2001 Sep-Oct
Prior aspirin use in unstable angina predisposes to higher risk: the aspirin paradox.
2001 Sep-Oct
An integrated clinical approach to predicting the benefit of tirofiban in non-ST elevation acute coronary syndromes. Application of the TIMI Risk Score for UA/NSTEMI in PRISM-PLUS.
2002 Feb
Cost effectiveness of invasive strategy in unstable coronary disease--what are we waiting for?
2002 Jan
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:03:31 GMT 2023
Edited
by admin
on Sat Dec 16 17:03:31 GMT 2023
Record UNII
GGX234SI5H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIROFIBAN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
TIROFIBAN [MI]
Common Name English
TIROFIBAN [VANDF]
Common Name English
AGRASTAT
Brand Name English
TIROFIBAN [HSDB]
Common Name English
tirofiban [INN]
Common Name English
Tirofiban [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000008832
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
WHO-ATC B01AC17
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
NCI_THESAURUS C1327
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
NDF-RT N0000008832
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
WHO-VATC QB01AC17
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
LIVERTOX 970
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
NDF-RT N0000175578
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
Code System Code Type Description
RXCUI
73137
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY RxNorm
SMS_ID
100000082118
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
DRUG BANK
DB00775
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
MESH
C078823
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
EVMPD
SUB11118MIG
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
PUBCHEM
60947
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
DAILYMED
GGX234SI5H
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
MERCK INDEX
m10890
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
TIROFIBAN
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
INN
7345
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL916
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
HSDB
7323
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
CAS
144494-65-5
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
CHEBI
9605
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
FDA UNII
GGX234SI5H
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
DRUG CENTRAL
2680
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
IUPHAR
6586
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID20162730
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
NCI_THESAURUS
C76405
Created by admin on Sat Dec 16 17:03:32 GMT 2023 , Edited by admin on Sat Dec 16 17:03:32 GMT 2023
PRIMARY
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TARGET->INHIBITOR OF AGGREGATION
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SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
BINDING
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SALT/SOLVATE -> PARENT
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