For treatment, in combination with heparin, of acute coronary syndrome, including patients who are to be managed medically and those undergoing PTCA or atherectomy.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Prevention of	Cardiovascular event		••••••••••••
Prevention of	Cardiovascular event		••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Tirofiban prevents the blood from clotting during episodes of chest pain or a heart attack, or while the patient is undergoing a procedure to treat a blocked coronary artery. It is a non-peptide antagonist of the platelet glycoprotein (GP) IIb/IIIa receptor, and inhibits platelet aggregation. When administered intravenously, tirofiban inhibits ex vivo platelet aggregation in a dose- and concentration-dependent manner. When given according to the recommended regimen, >90% inhibition is attained by the end of the 30-minute infusion. Tirofiban has been recently shown in patients with unstable angina to reduce ischemic events at 48 hours following infusion when compared to standard heparin therapy.

Mechanism of action

Tirofiban is a reversible antagonist of fibrinogen binding to the GP IIb/IIIa receptor, the major platelet surface receptor involved in platelet aggregation. Platelet aggregation inhibition is reversible following cessation of the infusion of tirofiban.

Target	Actions	Organism
AIntegrin alpha-IIb	antagonist	Humans
AIntegrin beta-3	antagonist	Humans

Absorption

Not Available

Volume of distribution

22 to 42 L

Protein binding

65%

Metabolism

Metabolism appears to be limited.

Route of elimination

It is cleared from the plasma largely by renal excretion, with about 65% of an administered dose appearing in urine and about 25% in feces, both largely as unchanged tirofiban.

Half-life

2 hours

Clearance

213 - 314 mL/min [Healthy subjects]
152 - 267 mL/min [patients with coronary artery disease]

Adverse Effects

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Toxicity

Not Available

Pathways

Pathway	Category
Tirofiban Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
Abacavir	Tirofiban may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The risk or severity of bleeding can be increased when Tirofiban is combined with Abciximab.
Abrocitinib	The risk or severity of bleeding and thrombocytopenia can be increased when Tirofiban is combined with Abrocitinib.
Aceclofenac	The risk or severity of bleeding can be increased when Aceclofenac is combined with Tirofiban.
Acemetacin	The risk or severity of bleeding can be increased when Acemetacin is combined with Tirofiban.

Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tirofiban hydrochloride	6H925F8O5J	150915-40-5	HWAAPJPFZPHHBC-FGJQBABTSA-N

International/Other Brands

Aggribloc (Abbott) / Agrastat (Merck Sharp & Dohme)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Aggrastat	Injection, solution	5 mg/100mL	Intravenous	Medicure International Inc	1998-05-14	Not applicable
Aggrastat	Liquid	0.25 mg / mL	Intravenous	Correvio (Uk) Ltd	1999-09-16	2013-02-06
Aggrastat	Solution	12.5 mg / 250 mL	Intravenous	Cipher Pharmaceuticals Inc.	2002-05-01	Not applicable
Aggrastat	Injection, solution	3.75 mg/15mL	Intravenous	Medicure International Inc	2016-10-15	Not applicable
Aggrastat	Injection, solution	3.75 mg/15mL	Intravenous	Medicure International Inc	2016-10-15	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Tirofiban	Injection, solution	12.5 mg/250mL	Intravenous	Eugia US LLC	2023-05-01	Not applicable
Tirofiban	Injection, solution	5 mg/100mL	Intravenous	Eugia US LLC	2023-05-01	Not applicable
Tirofiban hydrochloride	Injection, solution	12.5 mg/250mL	Intravenous	Gland Pharma Limited	2021-04-15	Not applicable
Tirofiban Hydrochloride	Injection	50 ug/1mL	Intravenous	Nexus Pharmaceuticals LLC	2023-09-25	Not applicable
Tirofiban Hydrochloride	Injection	50 ug/1mL	Intravenous	Nexus Pharmaceuticals LLC	2023-09-25	Not applicable

Chemical Identifiers

UNII: GGX234SI5H
CAS number: 144494-65-5
InChI Key: COKMIXFXJJXBQG-NRFANRHFSA-N
InChI: 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
IUPAC Name: (2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid
SMILES: CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O

References

Synthesis Reference

George Roby Thomas, Dawson James Reimer, Albert D. Friesen, "TRANSDERMAL PHARMACEUTICAL PREPARATION AND ADMINISTRATION OF TIROFIBAN." U.S. Patent US20120029447, issued February 02, 2012.

US20120029447

General References

Not Available

External Links

Human Metabolome Database: HMDB0014913
KEGG Compound: C07965
PubChem Compound: 60947
PubChem Substance: 46504678
ChemSpider: 54912
BindingDB: 50004058
RxNav: 73137
ChEBI: 9605
ChEMBL: CHEMBL916
ZINC: ZINC000003806104
Therapeutic Targets Database: DAP000696
PharmGKB: PA451698
PDBe Ligand: AGG
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Tirofiban

PDB Entries

2vdm / 7td8

FDA label

Download (59.1 KB)

Clinical Trials

Clinical Trials Clinical Trial & Rare Diseases Add-on Data Package Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package

Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
Not Available	Recruiting	Treatment	Acute Ischemic Stroke	1	somestatus	stop reason	just information to hide
Not Available	Terminated	Not Available	Acute Coronary Syndrome (ACS) / Coronary Artery Disease (CAD)	1	somestatus	stop reason	just information to hide
Not Available	Terminated	Not Available	Non ST Segment Elevation Myocardial Infarction (NSTEMI)	1	somestatus	stop reason	just information to hide
Not Available	Unknown Status	Prevention	Elective Percutaneous Coronary Intervention / ST Segment Elevation Myocardial Infarction (STEMI)	1	somestatus	stop reason	just information to hide
Not Available	Unknown Status	Prevention	Primary Percutaneous Coronary Intervention / ST Segment Elevation Myocardial Infarction (STEMI)	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Medicure international inc

Packagers

Baxter International Inc.
Ben Venue Laboratories Inc.
Guilford Pharmaceuticals
Iroko Pharmaceuticals
Medicure International Inc.
Merck & Co.

Dosage Forms

Form	Route	Strength
Injection, solution	Intravenous	0.05 MG/ML
Injection, solution	Intravenous	3.75 mg/15mL
Injection, solution	Intravenous	5 mg/100mL
Injection, solution, concentrate	Intravenous; Parenteral	250 MICROGRAMMI/ML
Liquid	Intravenous	0.25 mg / mL
Solution	Intravenous	12.5 mg / 250 mL
Injection, solution, concentrate	Intravenous	0.25 mg/mL
Injection, solution, concentrate	Parenteral	250 Mikrogramm/ml
Solution	Parenteral	50 Mikrogramm/ml
Injection	Intravenous	0.281 mg/mL
Injection, solution, concentrate	Intravenous	12.5 mg/50ml
Injection, solution, concentrate	Intravenous
Solution	Intravenous	14.045 mg
Injection, solution	Intravenous
Solution	Intravenous	12.500 mg
Solution	Intravenous	50 mcg/ml
Solution, concentrate	Intravenous	0.25 mg
Injection	Intravenous	50 ug/1mL
Injection	Not applicable	0.25 mg/1mL
Injection, solution	Intravenous	12.5 mg/250mL
Injection, solution	Parenteral	50 MICROGRAMMI/ML
Solution	Intravenous	12.5 mg
Injection	Intravenous	12.5 mg/50ml

Prices

Unit description	Cost	Unit
Aggrastat 250 mcg/ml vial	10.62USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5658929	No	1997-08-19	2010-09-27
CA2234364	No	2000-02-08	2016-10-23
CA2052073	No	1998-05-26	2011-09-23
US6770660	No	2004-08-03	2023-05-01
US5965581	No	1999-10-12	2016-10-23
US5978698	No	1999-11-02	2017-10-08
US5733919	No	1998-03-31	2016-10-23
US5972967	No	1999-10-26	2016-10-23
US6136794	No	2000-10-24	2019-01-29

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Very slightly soluble	Not Available
logP	1.4	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00317 mg/mL	ALOGPS
logP	1.78	ALOGPS
logP	0.6	Chemaxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.17	Chemaxon
pKa (Strongest Basic)	10.21	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	104.73 Å²	Chemaxon
Rotatable Bond Count	13	Chemaxon
Refractivity	117.48 m³·mol^-1	Chemaxon
Polarizability	49.27 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9934
Blood Brain Barrier	+	0.5951
Caco-2 permeable	-	0.6716
P-glycoprotein substrate	Substrate	0.8571
P-glycoprotein inhibitor I	Non-inhibitor	0.5443
P-glycoprotein inhibitor II	Non-inhibitor	0.9898
Renal organic cation transporter	Non-inhibitor	0.8435
CYP450 2C9 substrate	Non-substrate	0.7483
CYP450 2D6 substrate	Non-substrate	0.7803
CYP450 3A4 substrate	Substrate	0.5096
CYP450 1A2 substrate	Non-inhibitor	0.8569
CYP450 2C9 inhibitor	Non-inhibitor	0.8219
CYP450 2D6 inhibitor	Non-inhibitor	0.8967
CYP450 2C19 inhibitor	Non-inhibitor	0.7916
CYP450 3A4 inhibitor	Non-inhibitor	0.9023
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9498
Ames test	Non AMES toxic	0.7023
Carcinogenicity	Non-carcinogens	0.8449
Biodegradation	Not ready biodegradable	0.9525
Rat acute toxicity	2.3684 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5278
hERG inhibition (predictor II)	Inhibitor	0.7024

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0a4i-9233000000-449c9f26afd8b05e7422
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000x-0119800000-6c962f7ed5b4baeaf6e3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-2201900000-47118e4d816f3a137e0a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0uml-3469200000-7127488c54966085a8ff
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-9020000000-865b1743d92c05f533f2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0wvj-9531200000-b287e432f7623093ef9a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-7921100000-0512b7527e70419d1756
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	223.3032209	predicted	DarkChem Lite v0.1.0
[M-H]-	228.2209209	predicted	DarkChem Lite v0.1.0
[M-H]-	206.46861	predicted	DeepCCS 1.0 (2019)
[M+H]+	223.7370209	predicted	DarkChem Lite v0.1.0
[M+H]+	228.6238209	predicted	DarkChem Lite v0.1.0
[M+H]+	208.82661	predicted	DeepCCS 1.0 (2019)
[M+Na]+	223.9126209	predicted	DarkChem Lite v0.1.0
[M+Na]+	228.2066209	predicted	DarkChem Lite v0.1.0
[M+Na]+	215.95685	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. Integrin alpha-IIb

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Integrin alpha-IIb/beta-3 is a receptor for fibronectin, fibrinogen, plasminogen, prothrombin, thrombospondin and vitronectin. It recognizes the sequence R-G-D in a wide array of ligands. It recognizes the sequence H-H-L-G-G-G-A-K-Q-A-G-D-V in fibrinogen gamma chain. Following activation integrin alpha-IIb/beta-3 brings about platelet/platelet interaction through binding of soluble fibrinogen. This step leads to rapid platelet aggregation which physically plugs ruptured endothelial cell surface
Specific Function: Extracellular matrix binding
Gene Name: ITGA2B
Uniprot ID: P08514
Uniprot Name: Integrin alpha-IIb
Molecular Weight: 113375.96 Da

References

Theroux P, Alexander J Jr, Pharand C, Barr E, Snapinn S, Ghannam AF, Sax FL: Glycoprotein IIb/IIIa receptor blockade improves outcomes in diabetic patients presenting with unstable angina/non-ST-elevation myocardial infarction: results from the Platelet Receptor Inhibition in Ischemic Syndrome Management in Patients Limited by Unstable Signs and Symptoms (PRISM-PLUS) study. Circulation. 2000 Nov 14;102(20):2466-72. [Article]
Dickfeld T, Ruf A, Pogatsa-Murray G, Muller I, Engelmann B, Taubitz W, Fischer J, Meier O, Gawaz M: Differential antiplatelet effects of various glycoprotein IIb-IIIa antagonists. Thromb Res. 2001 Jan 15;101(2):53-64. [Article]
von Segesser LK, Mueller X, Marty B, Horisberger J, Corno A: Alternatives to unfractionated heparin for anticoagulation in cardiopulmonary bypass. Perfusion. 2001 Sep;16(5):411-6. [Article]
Kondo K, Umemura K: Clinical pharmacokinetics of tirofiban, a nonpeptide glycoprotein IIb/IIIa receptor antagonist: comparison with the monoclonal antibody abciximab. Clin Pharmacokinet. 2002;41(3):187-95. [Article]
Roffi M, Moliterno DJ, Meier B, Powers ER, Grines CL, DiBattiste PM, Herrmann HC, Bertrand M, Harris KE, Demopoulos LA, Topol EJ: Impact of different platelet glycoprotein IIb/IIIa receptor inhibitors among diabetic patients undergoing percutaneous coronary intervention: : Do Tirofiban and ReoPro Give Similar Efficacy Outcomes Trial (TARGET) 1-year follow-up. Circulation. 2002 Jun 11;105(23):2730-6. [Article]
Juwana YB, Suryapranata H, Ottervanger JP, van 't Hof AW: Tirofiban for myocardial infarction. Expert Opin Pharmacother. 2010 Apr;11(5):861-6. doi: 10.1517/14656561003690005. [Article]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	13.6	N/A	N/A	A28922
IC 50 (nM)	5	N/A	N/A	A28915
IC 50 (nM)	11	N/A	N/A	A28915 / A28918
IC 50 (nM)	260000	N/A	N/A	A28915 / A28916
IC 50 (nM)	100000	N/A	N/A	A28915
IC 50 (nM)	9	N/A	N/A	A28916 / A28917
IC 50 (nM)	62000	N/A	N/A	A28916
IC 50 (nM)	15	N/A	N/A	A28919 / A28921
IC 50 (nM)	36	N/A	N/A	A28920
IC 50 (nM)	>1000	N/A	N/A	A28921
IC 50 (nM)	0.95	N/A	N/A	A28922 / A28924
IC 50 (nM)	0.37	N/A	N/A	A28923
Kd (nM)	15	N/A	N/A	A28918
Kd (nM)	1.9	N/A	N/A	A28919
Kd (nM)	13	N/A	N/A	A28919

Details2. Integrin beta-3

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Integrin alpha-V/beta-3 (ITGAV:ITGB3) is a receptor for cytotactin, fibronectin, laminin, matrix metalloproteinase-2, osteopontin, osteomodulin, prothrombin, thrombospondin, vitronectin and von Willebrand factor. Integrin alpha-IIb/beta-3 (ITGA2B:ITGB3) is a receptor for fibronectin, fibrinogen, plasminogen, prothrombin, thrombospondin and vitronectin. Integrins alpha-IIb/beta-3 and alpha-V/beta-3 recognize the sequence R-G-D in a wide array of ligands. Integrin alpha-IIb/beta-3 recognizes the sequence H-H-L-G-G-G-A-K-Q-A-G-D-V in fibrinogen gamma chain. Following activation integrin alpha-IIb/beta-3 brings about platelet/platelet interaction through binding of soluble fibrinogen. This step leads to rapid platelet aggregation which physically plugs ruptured endothelial surface. Fibrinogen binding enhances SELP expression in activated platelets (By similarity). ITGAV:ITGB3 binds to fractalkine (CX3CL1) and acts as its coreceptor in CX3CR1-dependent fractalkine signaling (PubMed:23125415, PubMed:24789099). ITGAV:ITGB3 binds to NRG1 (via EGF domain) and this binding is essential for NRG1-ERBB signaling (PubMed:20682778). ITGAV:ITGB3 binds to FGF1 and this binding is essential for FGF1 signaling (PubMed:18441324). ITGAV:ITGB3 binds to FGF2 and this binding is essential for FGF2 signaling (PubMed:28302677). ITGAV:ITGB3 binds to IGF1 and this binding is essential for IGF1 signaling (PubMed:19578119). ITGAV:ITGB3 binds to IGF2 and this binding is essential for IGF2 signaling (PubMed:28873464). ITGAV:ITGB3 binds to IL1B and this binding is essential for IL1B signaling (PubMed:29030430). ITGAV:ITGB3 binds to PLA2G2A via a site (site 2) which is distinct from the classical ligand-binding site (site 1) and this induces integrin conformational changes and enhanced ligand binding to site 1 (PubMed:18635536, PubMed:25398877). ITGAV:ITGB3 acts as a receptor for fibrillin-1 (FBN1) and mediates R-G-D-dependent cell adhesion to FBN1 (PubMed:12807887). In brain, plays a role in synaptic transmission and plasticity. Involved in the regulation of the serotonin neurotransmission, is required to localize to specific compartments within the synapse the serotonin receptor SLC6A4 and for an appropriate reuptake of serotonin. Controls excitatory synaptic strength by regulating GRIA2-containing AMPAR endocytosis, which affects AMPAR abundance and composition (By similarity). ITGAV:ITGB3 act as a receptor for CD40LG (PubMed:31331973). ITGAV:ITGB3 acts as a receptor for IBSP and promotes cell adhesion and migration to IBSP (PubMed:10640428)
Specific Function: Cell adhesion molecule binding
Gene Name: ITGB3
Uniprot ID: P05106
Uniprot Name: Integrin beta-3
Molecular Weight: 87056.975 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Juwana YB, Suryapranata H, Ottervanger JP, van 't Hof AW: Tirofiban for myocardial infarction. Expert Opin Pharmacother. 2010 Apr;11(5):861-6. doi: 10.1517/14656561003690005. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 15, 2024 21:55

Tirofiban

Identification

Structure for Tirofiban (DB00775)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References