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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H36N2O5S.ClH.H2O
Molecular Weight 495.0747
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIROFIBAN HYDROCHLORIDE

SMILES

CCCCS(=O)(=O)N[C@@]([H])(Cc1ccc(cc1)OCCCCC2CCNCC2)C(=O)O.Cl.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

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Bleeding risk of tirofiban, a nonpeptide GPIIb/IIIa platelet receptor antagonist in progressive stroke: an open pilot study.
2001
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
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
GP IIb/IIIa inhibitors in coronary artery disease management: what the latest trials tell us.
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
Treatment of acute basilar artery thrombosis with a combination of systemic alteplase and tirofiban, a nonpeptide platelet glycoprotein IIb/IIIa inhibitor: report of four cases.
2001 Dec
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
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
Deep venous thrombosis prophylaxis is not indicated for laparoscopic cholecystectomy.
2001 Jul-Sep
[Lysis of an extensive thrombus in the internal carotid artery using a glycoprotein IIb/IIIa receptor antagonist].
2001 Jun 8
Administration of abciximab to patients receiving tirofiban or eptifibatide: effect on platelet function.
2001 Mar 1
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
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
Acute coronary syndrome without ST elevation: implementation of new guidelines.
2001 Nov 3
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
Interpreting new treatment guidelines for non-ST-segment elevation acute coronary syndromes.
2001 Oct 18
Should patients with unstable coronary syndromes routinely undergo cardiac catheterization and appropriate revascularization?
2001 Sep
Resolution of a spontaneous coronary artery thrombus with a new antiplatelet agent.
2001 Sep
Pharmacodynamic characterization of the interaction between abciximab or tirofiban with unfractionated or a low molecular weight heparin in healthy subjects.
2001 Sep
Tirofiban therapy does not increase the risk of hemorrhage after emergency coronary surgery.
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
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
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 Jun 26 11:32:27 UTC 2021
Edited
by admin
on Sat Jun 26 11:32:27 UTC 2021
Record UNII
6H925F8O5J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIROFIBAN HYDROCHLORIDE
MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
TIROFIBAN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
TIROFIBAN HYDROCHLORIDE [USAN]
Common Name English
L-700462
Code English
AGGRASTAT
Brand Name English
TIROFIBAN HYDROCHLORIDE MONOHYDRATE [WHO-DD]
Common Name English
L-700,462
Code English
TIROFIBAN HYDROCHLORIDE [VANDF]
Common Name English
TIROFIBAN HCL
Common Name English
L-TYROSINE, N-(BUTYLSULFONYL)-O-(4-(4-PIPERIDINYL)BUTYL)-, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
TIROFIBAN HYDROCHLORIDE MONOHYDRATE
MI   WHO-DD  
Common Name English
N-(BUTYLSULFONYL)-4-(4-(4-PIPERIDYL)BUTOXY)-L-PHENYLALANINE MONOHYDROCHLORIDE MONOHYDRATE
Systematic Name English
TIROFIBAN HYDROCHLORIDE [MART.]
Common Name English
MK-383
Code English
TIROFIBAN HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
L-TYROSINE, N-(BUTYLSULFONYL)-O-(4-(4-PIPERIDINYL)BUTYL)-, MONOHYDROCHLORIDE, MONOHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
Code System Code Type Description
FDA UNII
6H925F8O5J
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
EPA CompTox
150915-40-5
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
RXCUI
253202
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY RxNorm
EVMPD
SUB22331
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
PUBCHEM
60946
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
CAS
150915-40-5
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL916
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
EVMPD
SUB04887MIG
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
NCI_THESAURUS
C47759
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
MERCK INDEX
M10890
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
Tirofiban hydrochloride
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
DRUG BANK
DBSALT001454
Created by admin on Sat Jun 26 11:32:27 UTC 2021 , Edited by admin on Sat Jun 26 11:32:27 UTC 2021
PRIMARY
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