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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014913
Secondary Accession Numbers
  • HMDB14913
Metabolite Identification
Common NameTirofiban
DescriptionTirofiban, also known as agrastat, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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. Tirofiban is a drug which is used for treatment, in combination with heparin, of acute coronary syndrome, including patients who are to be managed medically and those undergoing ptca or atherectomy. In humans, tirofiban is involved in the tirofiban action pathway. Tirofiban is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Tirofiban.
Structure
Data?1582753234
Synonyms
ValueSource
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acidChEBI
N-(Butylsulfonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosineChEBI
TirofibanumChEBI
AgrastatKegg
(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 monohydrateHMDB
Tirofiban hydrochlorideHMDB
Merck frosst brand OF tirofiban hydrochloride monohydrateHMDB
Merck brand OF tirofiban hydrochloride monohydrateHMDB
Tirofiban hydrochloride monohydrateHMDB
AggrastatHMDB
Cahill may roberts brand OF tirofiban hydrochloride monohydrateHMDB
MSD Brand OF tirofiban hydrochloride monohydrateHMDB
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
Description Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 g/LNot Available
LogP1.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity117.48 m³·mol⁻¹ChemAxon
Polarizability49.27 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+199.88231661259
DarkChem[M-H]-200.97231661259
DeepCCS[M+H]+208.82730932474
DeepCCS[M-H]-206.46930932474
DeepCCS[M-2H]-240.7330932474
DeepCCS[M+Na]+215.95730932474
AllCCS[M+H]+204.332859911
AllCCS[M+H-H2O]+202.432859911
AllCCS[M+NH4]+206.032859911
AllCCS[M+Na]+206.532859911
AllCCS[M-H]-196.132859911
AllCCS[M+Na-2H]-197.632859911
AllCCS[M+HCOO]-199.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TirofibanCCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O5101.8Standard polar33892256
TirofibanCCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O3476.1Standard non polar33892256
TirofibanCCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(O)=O3633.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tirofiban,1TMS,isomer #1CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C3562.2Semi standard non polar33892256
Tirofiban,1TMS,isomer #2CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O)[Si](C)(C)C3594.4Semi standard non polar33892256
Tirofiban,1TMS,isomer #3CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O3649.8Semi standard non polar33892256
Tirofiban,2TMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3571.5Semi standard non polar33892256
Tirofiban,2TMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3709.8Standard non polar33892256
Tirofiban,2TMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C4626.9Standard polar33892256
Tirofiban,2TMS,isomer #2CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C3604.1Semi standard non polar33892256
Tirofiban,2TMS,isomer #2CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C3762.8Standard non polar33892256
Tirofiban,2TMS,isomer #2CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C4763.1Standard polar33892256
Tirofiban,2TMS,isomer #3CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C3623.7Semi standard non polar33892256
Tirofiban,2TMS,isomer #3CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C3790.3Standard non polar33892256
Tirofiban,2TMS,isomer #3CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C4785.1Standard polar33892256
Tirofiban,3TMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3645.8Semi standard non polar33892256
Tirofiban,3TMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C3893.9Standard non polar33892256
Tirofiban,3TMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C4507.0Standard polar33892256
Tirofiban,1TBDMS,isomer #1CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C3775.2Semi standard non polar33892256
Tirofiban,1TBDMS,isomer #2CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C3806.3Semi standard non polar33892256
Tirofiban,1TBDMS,isomer #3CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O3870.7Semi standard non polar33892256
Tirofiban,2TBDMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4029.4Semi standard non polar33892256
Tirofiban,2TBDMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4206.3Standard non polar33892256
Tirofiban,2TBDMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCNCC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4604.6Standard polar33892256
Tirofiban,2TBDMS,isomer #2CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C4054.2Semi standard non polar33892256
Tirofiban,2TBDMS,isomer #2CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C4240.5Standard non polar33892256
Tirofiban,2TBDMS,isomer #2CCCCS(=O)(=O)N[C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C4805.0Standard polar33892256
Tirofiban,2TBDMS,isomer #3CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C4104.6Semi standard non polar33892256
Tirofiban,2TBDMS,isomer #3CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C4250.9Standard non polar33892256
Tirofiban,2TBDMS,isomer #3CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O)[Si](C)(C)C(C)(C)C4813.3Standard polar33892256
Tirofiban,3TBDMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4341.4Semi standard non polar33892256
Tirofiban,3TBDMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4601.2Standard non polar33892256
Tirofiban,3TBDMS,isomer #1CCCCS(=O)(=O)N([C@@H](CC1=CC=C(OCCCCC2CCN([Si](C)(C)C(C)(C)C)CC2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4551.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tirofiban GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9233000000-449c9f26afd8b05e74222017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tirofiban GC-MS (1 TMS) - 70eV, Positivesplash10-0a4j-9241200000-c8cce3f0150c49c7b4b92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tirofiban GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 10V, Positive-QTOFsplash10-006y-0549500000-2974f1cff243a2edea702016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 20V, Positive-QTOFsplash10-05fr-8978100000-c82b954a66a21d7b7b162016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 40V, Positive-QTOFsplash10-052f-4960000000-99f01b2e16edac7fb8822016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 10V, Negative-QTOFsplash10-000i-0417900000-2def9a867e11bd4431b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 20V, Negative-QTOFsplash10-00di-2947100000-e78108adb072e11a5add2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 40V, Negative-QTOFsplash10-024u-6940000000-5ebd43e473a27543a0152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 10V, Positive-QTOFsplash10-0006-0016900000-2cd3d85cb7f7753eceb72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 20V, Positive-QTOFsplash10-004i-1096000000-d6ff280138c0c8f31cb82021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 40V, Positive-QTOFsplash10-0006-8910000000-a1aaa15fb128bd3ad5a32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 10V, Negative-QTOFsplash10-00kr-1502900000-6b2945d27bec9c4187492021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 20V, Negative-QTOFsplash10-00di-9024000000-1371a4b5fb1f8011211d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tirofiban 40V, Negative-QTOFsplash10-022a-9431100000-8c15bfa5f044a4504b3f2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00775 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00775 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00775
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54912
KEGG Compound IDC07965
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTirofiban
METLIN IDNot Available
PubChem Compound60947
PDB IDNot Available
ChEBI ID9605
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]