Tirofiban

Base Information

• Chemical Name: Tirofiban
• CAS No.: 144494-65-5
• Deprecated CAS: 151065-53-1
• Molecular Formula: C22H36N2O5S
• Molecular Weight: 477.065
• Hs Code.: 2942000000
• European Community (EC) Number: 635-682-4
• UNII: GGX234SI5H
• DSSTox Substance ID: DTXSID20162730
• Nikkaji Number: J523.557J
• Wikipedia: Tirofiban
• Wikidata: Q415366
• NCI Thesaurus Code: C76405
• RXCUI: 73137
• Pharos Ligand ID: 9WTWYH1JU53L
• Metabolomics Workbench ID: 43070
• ChEMBL ID: CHEMBL916
• Mol file: 144494-65-5.mol

Synonyms:Aggrastat;Agrastat;L 700,462;L 700462;L-700,462;L-700462;L700,462;MK 383;MK-383;N-(butylsulfonyl)-O-(4-(4-piperidyl)butyl)-L-tyrosine;tirofiban;tirofiban hydrochloride;tirofiban hydrochloride monohydrate

Chemical Property of Tirofiban

Chemical Property:

• Vapor Pressure: 8.09E-16mmHg at 25°C
• Melting Point: 223-225oC
• Refractive Index: 1.531
• Boiling Point: 611.7 °C at 760 mmHg
• PKA: 3.37±0.10(Predicted)
• Flash Point: 323.7 °C
• PSA: 113.11000
• Density: 1.154 g/cm³
• LogP: 4.75100
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 440.23449343
• Heavy Atom Count: 30
• Complexity: 579

Purity/Quality:

99% ^*data from raw suppliers

Tirofiban ≥98.5% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCS(=O)(=O)NC(CC1=CC=C(C=C1)OCCCCC2CCNCC2)C(=O)O
• Isomeric SMILES: CCCCS(=O)(=O)N[C@@H](CC1=CC=C(C=C1)OCCCCC2CCNCC2)C(=O)O
• Recent ClinicalTrials: Reduction of Microembolism After the Intervention Surgery of Intracranial Aneurysms by Administration of Tirofiban
• Recent EU Clinical Trials: Facilitation through Aggrastat or cangrelor Bolus and infusion Over prasugreL: a muUlticenter randomized open-label trial in patientS with ST-elevation myocardial inFarction referred for primAry percutaneouS inTERvention.
• 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.
• 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

Technology Process of Tirofiban

There total 43 articles about Tirofiban which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

N-(n-butanesulfonyl)-O-(4-(4-pyridinyl)-butyl)-(S)-tyrosine (149490-61-9) → tirofiban (144494-65-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 60 ℃; for 5.5h; under 2068.6 Torr;

DOI:10.1016/S0040-4020(01)87943-6

Reference yield: 95.7%

tirofiban (144494-65-5) → tirofiban hydrochloride (144494-65-5)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 6h;

Reference yield: 95.0%

C31H52N2O7S → tirofiban hydrochloride (144494-65-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 80 ℃; for 8h;

upstream raw materials:

4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-2-carboxy-ethyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester

pyridine-4-acetic acid

4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester

tert-butyl 4-(formylmethyl)piperidine-1-carboxylate

Refernces

• 1、 -. "A method for one-step synthesis of carboxylic acids with two extended carbon chains from olefins". . . Retrieved 2020/10/12.
• 2、 -. "Synthesis method of tirofiban hydrochloride intermediate III (by machine translation)". Paragraph 0082-0085. . Retrieved 2020/06/02.