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
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
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 |
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19343166 |
15.0 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AGGRASTAT Approved UseAGGRASTAT, 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 Date1998 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
193.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7955799/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7955799/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7955799/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7955799/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7955799/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7955799/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/10534322/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10534322/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10534322/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10534322/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10534322/ Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19742428
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
Edited
Sat Dec 16 17:03:31 GMT 2023
by
admin
on
Sat Dec 16 17:03:31 GMT 2023
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Record UNII |
GGX234SI5H
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Record Status |
Validated (UNII)
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Record Version |
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-
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NDF-RT |
N0000008832
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WHO-ATC |
B01AC17
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NCI_THESAURUS |
C1327
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N0000008832
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QB01AC17
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970
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N0000175578
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m10890
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TIROFIBAN
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C76405
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TARGET -> INHIBITOR |
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