4-methylbenzene-1-sulfonic acid; N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-[5-({[2-methanesulfonyl(1,2-13C2)ethyl]amino}methyl)furan-2-yl]quinazolin-4-amine

• ChemBase ID: 172221
• Molecular Formular: C36H34ClFN4O7S2
• Molecular Mass: 756.23788177
• Monoisotopic Mass: 755.15789192
• SMILES: c1c(ccc(c1)C)S(=O)(=O)O.c1c(cc2c(c1)ncnc2Nc1ccc(c(c1)Cl)OCc1cccc(c1)F)c1oc(cc1)C[15NH][13CH2][13CH2]S(=O)(=O)C
• Canonical SMILES: Fc1cccc(c1)COc1ccc(cc1Cl)Nc1ncnc2c1cc(cc2)c1ccc(o1)C[15NH][13CH2][13CH2]S(=O)(=O)C.Cc1ccc(cc1)S(=O)(=O)O
• InChI: InChI=1S/C29H26ClFN4O4S.C7H8O3S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19;1-6-2-4-7(5-3-6)11(8,9)10/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35);2-5H,1H3,(H,8,9,10)/i11+1,12+1,32+1
• InChIKey: OZDXXJABMOYNGY-OSUMFKEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methylbenzene-1-sulfonic acid; N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-[5-({[2-methanesulfonyl(1,2-^1^3C₂)ethyl]amino}methyl)furan-2-yl]quinazolin-4-amine
• IUPAC Traditional name: N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-[5-({[2-methanesulfonyl(1,2-^1^3C₂)ethyl]amino}methyl)furan-2-yl]quinazolin-4-amine; toluenesulfonic acid
• Synonyms: N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[[[2-(methylsulfonyl)ethyl]amino]methyl]-2-furanyl]-4-quinazolinamine Bis(4-methylbenzenesulfonate)-13C2,15N Ditosylate; GW-572016F-13C2,15N; Tykerb-13C2,15N Ditosylate; Lapatinib-13C2,15N Ditosylate

Database IDs

• PubChem SID: 164228131
• PubChem CID: 71749747

CALCULATED PROPERTIES

• Acid pKa: 15.986492
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.9310408
• LogD (pH = 7.4): 4.425011
• Log P: 4.638509
• Molar Refractivity: 152.4172 cm^3
• Polarizability: 61.300476 Å^3
• Polar Surface Area: 106.35 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 247-249°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L175802

Labelled Lapatinib (L175800). Reversible dual inhibitor of ErbB1 and ErbB2 tyrosine kinases. Antineoplastic.

REFERENCES

• Kim, T.E., et al.: Drugs, 6, 886 (2003)
• Wood, E.R., et al.: Cancer Res., 64, 6652 (2003)
• Spector, N.L., et al.: J. Clin. Oncol., 23, 2502 (2003)