Tirofiban (CED0004164)

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:53 UTC

Update Date

2026-08-21 23:09:30 UTC

Accession Number

CHEM022181

Identification

Common Name

Tirofiban

Class

Small Molecule

Description

Tirofiban is an organic compound with the formula C22H36N2O5S and an average molecular weight of 440.60 g/mol. Tirofiban belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. Used as an antithrombotic agent within healthcare, pharmaceuticals, and veterinary products, the compound is administered via intravenous exposure. It acts as an antagonist of two protein targets: Integrin alpha-IIb (ITGA2B) and Integrin beta-3 (ITGB3).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acid	ChEBI
N-(Butylsulfonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosine	ChEBI
Tirofibanum	ChEBI
Agrastat	Kegg
(2S)-2-(Butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoate	Generator
(2S)-2-(Butylsulphonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoate	Generator
(2S)-2-(Butylsulphonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acid	Generator
N-(Butylsulphonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosine	Generator
Merck sharp and dohme brand OF tirofiban hydrochloride monohydrate	HMDB
Tirofiban hydrochloride	HMDB
Merck frosst brand OF tirofiban hydrochloride monohydrate	HMDB
Merck brand OF tirofiban hydrochloride monohydrate	HMDB
Tirofiban hydrochloride monohydrate	HMDB
Aggrastat	HMDB
Cahill may roberts brand OF tirofiban hydrochloride monohydrate	HMDB
MSD Brand OF tirofiban hydrochloride monohydrate	HMDB

Chemical Formula

C₂₂H₃₆N₂O₅S

Average Molecular Mass

440.597 g/mol

Monoisotopic Mass

440.234 g/mol

CAS Registry Number

144494-65-5

IUPAC Name

(2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid

Traditional Name

tirofiban

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 Key

COKMIXFXJJXBQG-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:9605 )
sulfonamide (CHEBI:9605 )
L-tyrosine derivative (CHEBI:9605 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0032 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-9233000000-449c9f26afd8b05e7422	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4j-9241200000-c8cce3f0150c49c7b4b9	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006y-0549500000-2974f1cff243a2edea70	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-8978100000-c82b954a66a21d7b7b16	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-4960000000-99f01b2e16edac7fb882	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0417900000-2def9a867e11bd4431b8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2947100000-e78108adb072e11a5add	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-024u-6940000000-5ebd43e473a27543a015	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0016900000-2cd3d85cb7f7753eceb7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1096000000-d6ff280138c0c8f31cb8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-8910000000-a1aaa15fb128bd3ad5a3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-1502900000-6b2945d27bec9c418749	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9024000000-1371a4b5fb1f8011211d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-022a-9431100000-8c15bfa5f044a4504b3f	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2524.0	Log mg/kg	[1400:4500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
273	Antithrombotic agents	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

3 pathways

Tirofiban Action Pathway

Tirofiban Action Pathway (new)

Tirofiban Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Plasminogen	P00747	Humans	Predicted (SEA)	80.9632
Click to view 3D structure	Plasma kallikrein	P03952	Humans	Predicted (SEA)	65.549
Click to view 3D structure	Coagulation factor X	P00742	Humans	Predicted (SEA)	94.2754
Click to view 3D structure	Coagulation factor XI	P03951	Humans	Predicted (SEA)	42.9728
Click to view 3D structure	Vitamin K-dependent protein C	P04070	Humans	Predicted (SEA)	10.821
Click to view 3D structure	Transcription initiation factor IIA subunit 1	P52655	Humans	Predicted (SEA)	2.41333
Click to view 3D structure	Complement C1s subcomponent	P09871	Humans	Predicted (SEA)	3.26967
Click to view 3D structure	Coagulation factor XII	P00748	Humans	Predicted (SEA)	57.0635
Click to view 3D structure	UDP-3-O-acyl-N-acetylglucosamine deacetylase	O67648	Aquifex aeolicus (strain VF5)	Predicted (SEA)	14.3243
Click to view 3D structure	Tissue-type plasminogen activator	P00750	Humans	Predicted (SEA)	34.7986
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	260.951
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	296.372
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Predicted (SEA)	153.363
Click to view 3D structure	Collagenase 3	P45452	Humans	Predicted (SEA)	264.921
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1262.48
Click to view 3D structure	Peroxisome proliferator-activated receptor alpha	Q07869	Humans	Predicted (SEA)	138.494
Click to view 3D structure	Interstitial collagenase	P03956	Humans	Predicted (SEA)	282.982
Click to view 3D structure	Neutrophil collagenase	P22894	Humans	Predicted (SEA)	278.077
Click to view 3D structure	Stromelysin-1	P08254	Humans	Predicted (SEA)	275.431
Click to view 3D structure	Matrix metalloproteinase-14	P50281	Humans	Predicted (SEA)	281.114
Click to view 3D structure	A disintegrin and metalloproteinase with thrombospondin motifs 4	O75173	Humans	Predicted (SEA)	65.549
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37238	Mus musculus	Predicted (SEA)	30.984
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	919.399
Click to view 3D structure	Transient receptor potential cation channel subfamily V member 3	Q8K424	Mus musculus	Predicted (SEA)	52.4704
Click to view 3D structure	Peroxisome proliferator-activated receptor delta	Q03181	Humans	Predicted (SEA)	133.356