2-chloro-4-{[6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-yl]amino}phenol; 4-methylbenzene-1-sulfonic acid

• ChemBase ID: 165561
• Molecular Formular: C29H29ClN4O7S2
• Molecular Mass: 645.14616
• Monoisotopic Mass: 644.11661897
• SMILES: c1c(ccc(c1)C)S(=O)(=O)O.c1c(cc2c(c1)ncnc2Nc1ccc(c(c1)Cl)O)c1oc(cc1)CNCCS(=O)(=O)C
• Canonical SMILES: Oc1ccc(cc1Cl)Nc1ncnc2c1cc(cc2)c1ccc(o1)CNCCS(=O)(=O)C.Cc1ccc(cc1)S(=O)(=O)O
• InChI: InChI=1S/C22H21ClN4O4S.C7H8O3S/c1-32(29,30)9-8-24-12-16-4-7-21(31-16)14-2-5-19-17(10-14)22(26-13-25-19)27-15-3-6-20(28)18(23)11-15;1-6-2-4-7(5-3-6)11(8,9)10/h2-7,10-11,13,24,28H,8-9,12H2,1H3,(H,25,26,27);2-5H,1H3,(H,8,9,10)
• InChIKey: CEZSDANEQYBUOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-4-{[6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-yl]amino}phenol; 4-methylbenzene-1-sulfonic acid
• IUPAC Traditional name: 2-chloro-4-{[6-(5-{[(2-methanesulfonylethyl)amino]methyl}furan-2-yl)quinazolin-4-yl]amino}phenol; toluenesulfonic acid
• Synonyms: 2-Chloro-4-[[6-[5-[[[2-(methylsulfonyl)ethyl]amino]methyl]-2-furanyl]-4-quinazolinyl]amino]phenol Ditosylate; O-De(3-fluorobenzyl) Lapatinib Ditosylate Salt

Database IDs

• PubChem SID: 162259694
• PubChem CID: 71315270

CALCULATED PROPERTIES

• Acid pKa: 8.805073
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.918484
• LogD (pH = 7.4): 2.395626
• Log P: 2.4976413
• Molar Refractivity: 123.1059 cm^3
• Polarizability: 50.14413 Å^3
• Polar Surface Area: 117.35 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: >176°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D228750

A reactive metabolite of Lapatinib (L175800) which is associated with various drug toxicities. Lapatinib is metabolized mainly by P450 3A4 to form O- and N-dealkylated metabolites.

REFERENCES

• He, K., et al.: Chem. Res. Toxicol., 11, 252 (1998)
• Rusnuk, D., et al.: Cancer Res., 61, 7196 (1998)
• Li, X., et al.: Drug Metab. Dispos., 37, 1242 (1998)