Tirofiban hydrochloride anhydrous
Basic information
- CAS
142373-60-2- Standard SMILES
CCCCS(=O)(=O)N[C@@H](Cc1ccc(OCCCCC2CCNCC2)cc1)C(=O)O.Cl- InChIKey
KPKFFYOMPGOQRP-BOXHHOBZSA-N- Molecular formula
- C22H37ClN2O5S
- Average molar mass
- 477.1 g/mol
- Monoisotopic mass
- 476.2111712
Overview
Tirofiban Hydrochloride is the hydrochloride salt form of tirofiban, a non-peptide tyrosine derivative with anticoagulant property. Tirofiban antagonizes fibrinogen binding to the platelet cell surface receptor, glycoprotein (GP) IIb/IIIA complex, one of the two purinergic receptors activated by ADP. The antagonism prevents adenylyl cyclase activation, which mediated via GP IIb/IIIa receptor complex, and results in decreased levels of cAMP and thereby interferes with platelet membrane function and subsequent platelet-platelet interaction, release of platelet granule constituents and prolongation of bleeding time.
Names & identifiers
- Preferred name
- Tirofiban hydrochloride anhydrous
- IUPAC
- (2S)-2-(butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoic acid;hydrochloride
- English name
- Tirofiban hydrochloride monohydrate
- Molecular formula
- C22H39ClN2O6S
- Molecular weight
- 495.07
Names & synonyms
Tirofiban hydrochloride anhydrousIKE1P4X57JRefChem:1100142TIROFIBAN HYDROCHLORIDE142373-60-2Tirofiban HClAggrastatTirofiban (hydrochloride)(S)-2-(Butylsulfonamido)-3-(4-(4-(piperidin-4-yl)butoxy)phenyl)propanoic acid hydrochlorideL-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-, monohydrochlorideL-Tyrosine, N-(butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-,monohydrochlorideC22H37ClN2O5S
Show more names
butoxy)L 7004624-Dihydroxypyridine-3-(4-(4-(piperidin-4-yl)TirofibanhydrochlorideHClTirofiban hydrochloride 1-hydrateTirofiban hydrochloride (L700462)Tirofiban hydrochloride monohydrate Tirofiban HydrochlorideN-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine hydrochloride
UNII-IKE1P4X57J142373-60-2 (HCl)N-(Butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-L-tyrosine monohydrochlorideCHEMBL1704SCHEMBL41327orb1705571DTXSID70931418EX-A2875
Properties
Computed structural properties
- Topological polar surface area
- 113 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 14
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 579
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 83 · 83-87oC
- solubility
- Methanol (Slightly)
- form
- Solid
- color
- White
- InChIKey
- HWAAPJPFZPHHBC-MGIYCFTINA-N
- SMILES
- S(CCCC)(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OCCCCC1CCNCC1)C(O)=O.Cl.O |&1:8,r|
- CAS DataBase Reference
- 142373 · 142373-60-2
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 P4X57J · IKE1P4X57J
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Tirofiban hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
TIROFIBAN HYDROCHLORIDE
Decreased Platelet Aggregation [PE]; Platelet Aggregation Inhibitor [EPC]
Applications
DescriptionTirofiban was launched as Aggrastat in Switzerland and the US for patients with unstable angina or non-Q-wave myocardial infarction to prevent cardiac ischemic events. Tirofiban is synthesized from (S)-tyrosine by a fourstep process. Tirofiban is a novel highly potent antiplatelet agent that inhibits the interaction of fibrinogen with GPⅡb/Ⅲa, an activated platelet membrane-bound glycoprotein complex. It prevents arterial thrombus formation in a dosedependent manner. Clinical efficacy was highly significant with an absolute and relative risk reduction. In these studies, treatment with tirofiban was well tolerated, without significant adverse effects.
UsesAggrastat (Millot Laboratories, France).
UsesTirofiban Hydrochloride is a selective nonpeptide platelet glycoprotein IIb/IIIa antagonist.
Upstream & downstream products
Upstream raw materials
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Compound notes
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