N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(2-{[(2-methanesulfonylethyl)amino]methyl}-1,3-thiazol-4-yl)quinazolin-4-amine dihydrochloride

• ChemBase ID: 154396
• Molecular Formular: C28H27Cl3FN5O3S2
• Molecular Mass: 671.0330832
• Monoisotopic Mass: 669.06049301
• SMILES: CS(=O)(=O)CCNCc1nc(cs1)c1ccc2c(c1)c(ncn2)Nc1ccc(c(c1)Cl)OCc1cccc(c1)F.Cl.Cl
• Canonical SMILES: Fc1cccc(c1)COc1ccc(cc1Cl)Nc1ncnc2c1cc(cc2)c1csc(n1)CNCCS(=O)(=O)C.Cl.Cl
• InChI: InChI=1S/C28H25ClFN5O3S2.2ClH/c1-40(36,37)10-9-31-14-27-35-25(16-39-27)19-5-7-24-22(12-19)28(33-17-32-24)34-21-6-8-26(23(29)13-21)38-15-18-3-2-4-20(30)11-18;;/h2-8,11-13,16-17,31H,9-10,14-15H2,1H3,(H,32,33,34);2*1H
• InChIKey: WIMITXDBYLKRKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(2-{[(2-methanesulfonylethyl)amino]methyl}-1,3-thiazol-4-yl)quinazolin-4-amine dihydrochloride
• IUPAC Traditional name: N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-(2-{[(2-methanesulfonylethyl)amino]methyl}-1,3-thiazol-4-yl)quinazolin-4-amine dihydrochloride
• Synonyms: 4-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenylamino]-6-[2-[[2-(methylsulfonyl)ethyl]aminomethyl]-4-thiazolyl]quinazoline dihydrochloride; GW583340 dihydrochloride

Database IDs

• MDL Number: MFCD07370137
• PubChem SID: 162248535; 24895131
• PubChem CID: 16219404

CALCULATED PROPERTIES

• Acid pKa: 15.993641
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 3.484543
• LogD (pH = 7.4): 4.6855364
• Log P: 4.7760706
• Molar Refractivity: 154.3122 cm^3
• Polarizability: 62.217785 Å^3
• Polar Surface Area: 106.1 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble9 mg/mL
• Apperance: solid
• Melting Point: 259.8-262.4 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C28H25ClFN5O3S2 · 2HCl

DETAILS

Sigma Aldrich - G3545

Biochem/physiol Actions
Potent dual ErbB-2/EGFR tyrosine kinase inhibitor. IC50= 0.01 and 0.014 μM for EGFR and ErbB-2. Orally active.
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline