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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H36N2O5S
Molecular Weight 440.5986
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])(Cc1ccc(cc1)OCCCCC2CCNCC2)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 440.5986
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

8.9510399E11
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
Inhibition of tissue factor-activated platelets by low-molecular-weight heparins and glycoprotein IIb/IIIa receptor antagonist.
2001 Apr 15
Safety and efficacy of thrombolysis with alteplase (50 mg) plus tirofiban versus alteplase (100 mg) alone in acute myocardial infarction: preliminary findings.
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
The A-to-Z Trial: Methods and rationale for a single trial investigating combined use of low-molecular-weight heparin with the glycoprotein IIb/IIIa inhibitor tirofiban and defining the efficacy of early aggressive simvastatin therapy.
2001 Aug
Comparative efficacy of fibrinogen and platelet supplementation on the in vitro reversibility of competitive glycoprotein IIb/IIIa (alphaIIb/beta3) receptor-directed platelet inhibition.
2001 Aug
Platelet inhibition after glycoprotein IIb/IIIa inhibitor therapy.
2001 Dec 18
Glycoprotein IIb/IIIa receptor blockers in acute coronary syndromes.
2001 Dec 8
TACTICS-TIMI 18 shows positive results of invasive approach.
2001 Feb-Mar
Anti-GPIIb/IIIa drugs: current strategies and future directions.
2001 Jul
Use of ICHOR-platelet works to assess platelet function in patients treated with GP IIb/IIIa inhibitors.
2001 Jul
Glycoprotein IIb/IIIa inhibitors: more different than alike?
2001 Jul
Stability and compatibility of tirofiban hydrochloride during simulated Y-site administration with other drugs.
2001 Jul 1
Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta(3) integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin.
2001 Jul 31
Randomized comparison of ticlopidine and clopidogrel after intracoronary stent implantation in a broad patient population.
2001 Jul 31
Optimal treatment of acute coronary syndromes--an evolving strategy.
2001 Jun 21
Comparison of two platelet glycoprotein IIb/IIIa inhibitors, tirofiban and abciximab, for the prevention of ischemic events with percutaneous coronary revascularization.
2001 Jun 21
Comparison of early invasive and conservative strategies in patients with unstable coronary syndromes treated with the glycoprotein IIb/IIIa inhibitor tirofiban.
2001 Jun 21
Effect of Ca2+ chelation on the platelet inhibitory ability of the GPIIb/IIIa antagonists abciximab, eptifibatide and tirofiban.
2001 Mar
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
Glycoprotein IIb/IIIa antagonists and low-molecular weight heparin in acute coronary syndromes.
2001 May
Point-of-care measured platelet inhibition correlates with a reduced risk of an adverse cardiac event after percutaneous coronary intervention: results of the GOLD (AU-Assessing Ultegra) multicenter study.
2001 May 29
[Indications for intravenous GPIIb/IIIa receptor inhibitors in acute coronary syndrome without prolonged ST syndrome].
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
A comparison of total hospital costs for percutaneous coronary intervention patients receiving abciximab versus tirofiban.
2001 Oct
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. 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
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
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
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 Jun 26 14:51:47 UTC 2021
Edited
by admin
on Sat Jun 26 14:51:47 UTC 2021
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 [WHO-DD]
Common Name English
TIROFIBAN [VANDF]
Common Name English
AGRASTAT
Brand Name English
TIROFIBAN [HSDB]
Common Name English
TIROFIBAN [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000008832
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
WHO-ATC B01AC17
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
NCI_THESAURUS C1327
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
NDF-RT N0000008832
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
WHO-VATC QB01AC17
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
LIVERTOX 970
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
NDF-RT N0000175578
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
Code System Code Type Description
RXCUI
73137
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00775
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
MESH
C078823
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
EVMPD
SUB11118MIG
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
PUBCHEM
60947
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
MERCK INDEX
M10890
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TIROFIBAN
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
INN
7345
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
ChEMBL
CHEMBL916
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
HSDB
7323
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
CAS
144494-65-5
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
FDA UNII
GGX234SI5H
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
DRUG CENTRAL
2680
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
IUPHAR
6586
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
EPA CompTox
144494-65-5
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
NCI_THESAURUS
C76405
Created by admin on Sat Jun 26 14:51:48 UTC 2021 , Edited by admin on Sat Jun 26 14:51:48 UTC 2021
PRIMARY
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