ChemicalBook > CAS DataBase List > Tirofiban

Tirofiban

Product Name
Tirofiban
CAS No.
144494-65-5
Chemical Name
Tirofiban
Synonyms
Aggrastat;CS-584;C07965;MK-383;irofiban;TIROFIBAN;Tirofiban(L700462;Tirofiban USP/EP/BP;Tirofiban Impurity 10;Tirofiban/Tirofiban HCl
CBNumber
CB9169083
Molecular Formula
C22H36N2O5S
Formula Weight
440.6
MOL File
144494-65-5.mol
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Tirofiban Property

Melting point:
223-225°
Boiling point:
611.7±65.0 °C(Predicted)
Density 
1.154±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 
Limited solubility
form 
Solid
pka
3.37±0.10(Predicted)
color 
White to off-white
BRN 
6182267
CAS DataBase Reference
144494-65-5(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
RTECS 
YP2364100
Hazardous Substances Data
144494-65-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
30165
Product name
Tirofiban
Purity
≥98.5% (HPLC)
Packaging
5mg
Price
$235
Updated
2024/03/01
American Custom Chemicals Corporation
Product number
API0005653
Product name
TIROFIBAN
Purity
95.00%
Packaging
5MG
Price
$503.93
Updated
2021/12/16
Adipogen Life Sciences
Product number
CDX-T0153-M100
Product name
Tirofiban
Purity
≥99%(HPLC)
Packaging
100mg
Price
$1129
Updated
2021/12/16
AK Scientific
Product number
E042
Product name
Tirofiban
Packaging
5mg
Price
$165
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0005653
Product name
TIROFIBAN
Purity
95.00%
Packaging
250MG
Price
$1248.45
Updated
2021/12/16
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Tirofiban Chemical Properties,Usage,Production

Chemical Properties

Tirofiban is an Off-White to Pale Yellow Solid. It is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. The solubility of tirofiban in these solvents is approximately 30 mg/ml.

Originator

Aggrastat,Merck and Co., Inc.

Uses

Tirofiban (Aggrastatt, MK-0383; L-700,462) is a parenteral, highly specific, and potent GPIIb/IIIa antagonist that was approved for patient use in 1998 for the treatment of unstable angina and non-Q-wave myocardial infarction.
Tirofiban is a nonpeptide GP IIb/IIIa antagonist that binds reversibly to IIb/IIIa receptors. Tirofiban is a non-peptide reversible antagonist of the platelet integrin glycoprotein (GP) IIbIIIa receptor used as an antiplatelet drug.
Tirofiban is a small molecule inhibitor of the protein-protein interaction between fibrinogen and the platelet integrin receptor GP IIb/IIIa and is the first drug candidate whose origins can be traced to a pharmacophore-based virtual screening lead.

Definition

ChEBI: Tirofiban is a member of the class of piperidines that is L-tyrosine in which a hydrogen attached to the amino group is replaced by a butylsulfonyl group and in which the hydrogen attached to the phenolic hydroxy group is replaced by a 4-(piperidin-4-yl)butyl group. It has a role as a fibrin modulating drug, a platelet glycoprotein-IIb/IIIa receptor antagonist and an anticoagulant. It is a member of piperidines, a sulfonamide and a L-tyrosine derivative.

Manufacturing Process

The synthesis of tirofiban starts by reaction of tyrosine with bis-trimethylsilyl trifluoraceramide to give a derivative in which both functions -OH and COOH_x0002_are protected. Treatment of this intermediate with butylsulfonyl chloride gives the corresponding sulfonamide derivative; the quite labile silyl groups are then removed under mildly acidic conditions to give N-butylsulfonyl-tyrosine. In a parallel scheme, 4-picoline is converted to its anion by means of butyl lithium; this gives 4-(4-chlorobutyl)-pyridine on alkylation with 1-bromo-3- chloropropane. The reaction of this compound with N-butylsulfonyl-tyrosine in presence of NaOH gives the ether 2-butylsulfonyaminol-3-[4-pyridin-4-ylbutoxy-phenyl]propionic acid. Hydrogenation over palladium on charcoal then reduce the pyridine ring to a piperidine to afford the fibrinogen receptor antagonist tirofiban.

Therapeutic Function

Fibrinogen receptor antagonist

General Description

Tirofiban is a nonpeptide that appears unrelatedchemically to eptifibatide, but actually has many similarities.The chemical architecture incorporates a systemthat is mimicking the RGD moiety that is present in eptifibatide.This can be seen in the distance between the nitrogenof the piperidine ring, which mimics the basic nitrogen ofarginine in the RGD sequence, and the carboxylic acid,which mimics the acid of aspartate in the RGD sequence.The basic nitrogen and the carboxylic acid of tirofiban areseparated by approximately 15 to 17? (16–18 atoms). Thisis the optimum distance seen in the RGD sequence of theplatelet receptor. Tirofiban is useful in treating non–Q wavemyocardial infarction and unstable angina.

Clinical Use

Tirofiban is a member of a new class of antithrombotic agents known as the “ fibans”. These compounds have a structural similarity to disintegrin, which was originally isolated from snake venoms. The location of the –COO- and NH3+ in the fibans is identical to the distance between the same functional groups of the RGD loop of disintegrin, and as a result, the fibans are able to effectively block the binding of fibrinogen to the GPIIb/IIIa receptor in an reversible manor.

Drug interactions

Potentially hazardous interactions with other drugs
Iloprost: increased risk of bleeding.
Heparin: increased risk of bleeding

Metabolism

Tirofiban is eliminated largely unchanged in the urine, with some biliary excretion in the faeces.

Mode of action

Tirofiban is a reversible antagonist that inhibits platelet aggregation by reversibly binding to the receptor glycoprotein (GP) IIb/IIIa of human platelets, thus preventing the binding of fibrinogen. Inhibition of platelet aggregation occurs in a dose- and concentrationdependent manner.?

Tirofiban Preparation Products And Raw materials

Raw materials

1-Butanesulfonyl chloride L-Tyrosine N-Methylacetamide Microcrystalline cellulose Isopropyl acetate Tetrahydrofuran 1-Bromo-3-chloropropane Potassium bisulfate n-Butyllithium

Preparation Products

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Tirofiban Suppliers

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View Lastest Price from Tirofiban manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Tirofiban 144494-65-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Tirofiban 144494-65-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09
Zhuozhou Wenxi import and Export Co., Ltd
Product
Tirofiban 144494-65-5
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27

144494-65-5, TirofibanRelated Search:

Haloperidol 2,2,6,6-Tetramethyl-4-piperidinol Propionic acid tert-Butylchlorodiphenylsilane PHENYL VALERATE DROPERIDOL Phenyl salicylate Lithium tri-tert-butoxyaluminum hydride 4-(4-pyridinyl)butyl chloride hydrochloride Diphenyl ether N-Butylsulfonyl-O-(4-(4-pyridinyl)butyl)-L-tyrosine R-Tirofiban Tirofiban Impurity 3 PHENYL RESIN Tirofiban IMpurity (4,4'-Dipyridyl-1,5-Pentane) Tirofiban Impurity 11 Tirofiban Impurity 9 4-BUTYLPIPERIDINE

  • TIROFIBAN
  • (2s)-2-(butylsulfonylamino)-3-[4-[4-(4-piperidyl)butoxy]phenyl]propanoic acid
  • C07965
  • Aggrastat
  • MK-383
  • N-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine
  • CS-584
  • AGGRASTAT; L700462; MK383
  • Tirofiban(L700462
  • (2S)-2-(butylsulfonylamino)-3-[4-(4-piperidin-4-ylbutoxy)phenyl]propanoicacid
  • Tirofiban/Tirofiban HCl
  • irofiban
  • Tirofiban Impurity 10
  • Tirofiban USP/EP/BP
  • Tirofiban (S)-2-(butylsulfonamido)-3-(4-(4-(piperidin-4- yl)butoxy)phenyl)propanoic acid
  • (2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid
  • Tirofiban Hydrochloride Intermediate II
  • Tirofiban(L700462,MK383)
  • 144494-65-5
  • 144494-65-6
  • C22H30N2O5SD6
  • C22H36N2O5S
  • Inhibitors