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

• ChemBase ID: 178673
• Molecular Formular: C22H39ClN2O6S
• Molecular Mass: 495.07286
• Monoisotopic Mass: 494.22173566
• SMILES: C1NCCC(C1)CCCCOc1ccc(cc1)C[C@H](NS(=O)(=O)CCCC)C(=O)O.Cl.O
• Canonical SMILES: CCCCS(=O)(=O)N[C@H](C(=O)O)Cc1ccc(cc1)OCCCCC1CCNCC1.O.Cl
• InChI: InChI=1S/C22H36N2O5S.ClH.H2O/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);1H;1H2/t21-;;/m0../s1
• InChIKey: HWAAPJPFZPHHBC-FGJQBABTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid hydrate hydrochloride
• IUPAC Traditional name: tirofiban hydrate hydrochloride
• Synonyms: N-(Butylsulfonyl)-O-[4-(4-piperidynyl)butyl]-L-tyrosine Hydrochloride Hydrate; N-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine Monohydrochloride Monohydrate; Tirofiban Hydrochloride Hydrate

Database IDs

• CAS Number: 150915-40-5
• PubChem SID: 164234583
• PubChem CID: 60946

CALCULATED PROPERTIES

• Acid pKa: 3.1721346
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.59689605
• LogD (pH = 7.4): 0.59796107
• Log P: 0.598297
• Molar Refractivity: 117.4761 cm^3
• Polarizability: 47.10656 Å^3
• Polar Surface Area: 104.73 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 135-137°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T446750

Tirofiban is a specific nonpeptide platelet fibrinogen receptor (GPIIb/IIIa) antagonist. Tirofiban is an antithrombotic used in the treatment of unstable angina.

REFERENCES

• Barrett, J.S., et al.: Clin. Pharmacol. Ther., 56, 377 (1994)
• Lynch, J.J., et al.: J. Pharmacol. Exp. Ther., 272, 20 (1994)
• Theroux, P., et al.: N. Engl.J. Med., 338, 1488 (1994)