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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-25 12:17:26 UTC
HMDB IDHMDB0014913
Secondary Accession Numbers
  • HMDB14913
StatusExpected but not Quantified
Metabolite Identification
Common NameTirofiban
DescriptionTirofiban 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 reversible antagonist of the platelet glycoprotein (GP) IIb/IIIa receptor, and inhibits platelet aggregation.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acidChEBI
N-(Butylsulfonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosineChEBI
TirofibanumChEBI
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoateGenerator
(2S)-2-(Butylsulphonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoateGenerator
(2S)-2-(Butylsulphonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acidGenerator
N-(Butylsulphonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosineGenerator
Merck sharp and dohme brand OF tirofiban hydrochloride monohydrateMeSH
Tirofiban hydrochlorideMeSH
Merck frosst brand OF tirofiban hydrochloride monohydrateMeSH
Merck brand OF tirofiban hydrochloride monohydrateMeSH
AgrastatMeSH
Tirofiban hydrochloride monohydrateMeSH
AggrastatMeSH
Cahill may roberts brand OF tirofiban hydrochloride monohydrateMeSH
MSD Brand OF tirofiban hydrochloride monohydrateMeSH
Chemical FormulaC22H36N2O5S
Average Molecular Weight440.597
Monoisotopic Molecular Weight440.234492962
IUPAC Name(2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid
Traditional Nametirofiban
CAS Registry Number144494-65-5
SMILES
CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O
InChI Identifier
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
InChI KeyCOKMIXFXJJXBQG-NRFANRHFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • Organosulfonic acid amide
  • Organic sulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Ether
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Subcellular:
Biofluid and excreta:
Role
Industrial application:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.17e-03 g/LNot Available
LogP1.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0032 mg/mLALOGPS
logP1.78ALOGPS
logP0.6ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.73 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity117.48 m3·mol-1ChemAxon
Polarizability49.27 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tirofiban PathwayPw000293Pw000293 greyscalePw000293 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00775 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00775 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00775
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54912
KEGG Compound IDC07965
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTirofiban
NuGOwiki LinkHMDB0014913
METLIN IDNot Available
PubChem Compound60947
PDB IDAGG
ChEBI ID9605
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cell adhesion
Specific 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
Gene Name:
ITGA2B
Uniprot ID:
P08514
Molecular weight:
113376.0
References
  1. 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. [PubMed:11076818 ]
  2. 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. [PubMed:11342206 ]
  3. 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. [PubMed:11565896 ]
  4. 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. [PubMed:11929319 ]
  5. 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. [PubMed:12057986 ]
  6. 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. [PubMed:20210689 ]