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

• ChemBase ID: 655
• Molecular Formular: C22H36N2O5S
• Molecular Mass: 440.59664
• Monoisotopic Mass: 440.23449326
• SMILES: S(=O)(=O)(N[C@@H](Cc1ccc(OCCCCC2CCNCC2)cc1)C(=O)O)CCCC
• Canonical SMILES: CCCCS(=O)(=O)N[C@H](C(=O)O)Cc1ccc(cc1)OCCCCC1CCNCC1
• InChI: 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
• InChIKey: COKMIXFXJJXBQG-NRFANRHFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(butane-1-sulfonamido)-3-{4-[4-(piperidin-4-yl)butoxy]phenyl}propanoic acid
• IUPAC Traditional name: tirofiban
• Brand Name: AGG; Aggrastat; Tirofiban [BAN:INN]
• Synonyms: Tirofiban; (2S)-2-(Butylsulfonylamino)-3-{4-[4-(4-piperidyl)butoxy}phenyl propanoic acid; N-(Butylsulfonyl)-O-[4-(4-piperidinyl)butyl]-L-tyrosine; Tirofiban

Database IDs

• CAS Number: 144494-65-5
• MDL Number: MFCD05237246
• Beilstein Number: 6182267
• PubChem SID: 160964118; 46504678
• PubChem CID: 60947

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.78
• LOG S: -5.14
• Solubility (Water): 3.17e-03 g/l

PROPERTIES

Physical Property

• Solubility: Very slightly soluble
• Hydrophobicity(logP): 1.4

Safety Information

• RTECS: YP2364100
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.5% (HPLC)
• Empirical Formula (Hill Notation): C22H36N2O5S

DETAILS

DrugBank - DB00775

• Drug Groups: approved
• Description: Tirofiban prevents the blood from clotting during episodes of chest pain or a heart attack, or while the patient is undergoing a procedure to treat a blocked coronary artery. It is a non-peptide reversible antagonist of the platelet glycoprotein (GP) IIb/IIIa receptor, and inhibits platelet aggregation.
• Indication: For treatment, in combination with heparin, of acute coronary syndrome, including patients who are to be managed medically and those undergoing PTCA or atherectomy.
• Pharmacology: Tirofiban prevents the blood from clotting during episodes of chest pain or a heart attack, or while the patient is undergoing a procedure to treat a blocked coronary artery. It is a non-peptide antagonist of the platelet glycoprotein (GP) IIb/IIIa receptor, and inhibits platelet aggregation. When administered intravenously, tirofiban inhibits ex vivo platelet aggregation in a dose- and concentration-dependent manner. When given according to the recommended regimen, >90% inhibition is attained by the end of the 30-minute infusion. Tirofiban has been recently shown in patients with unstable angina to reduce ischemic events at 48 hours following infusion when compared to standard heparin therapy.
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolism appears to be limited.
• Half Life: 2 hours
• Protein Binding: 65%
• Elimination: It is cleared from the plasma largely by renal excretion, with about 65% of an administered dose appearing in urine and about 25% in feces, both largely as unchanged tirofiban.
• Distribution: * 22 to 42 L
• Clearance: * 213 - 314 mL/min [Healthy subjects]; * 152 - 267 mL/min [patients with coronary artery disease]
• External Links: Wikipedia; RxList; Drugs.com