(2E)-4-[bis(2H3)methylamino]-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)but-2-enamide

• ChemBase ID: 175079
• Molecular Formular: C30H29ClN6O3
• Molecular Mass: 557.04266
• Monoisotopic Mass: 556.1989665
• SMILES: c12c(c(c(cn1)C#N)Nc1cc(c(cc1)OCc1ncccc1)Cl)cc(c(c2)OCC)NC(=O)/C=C/CN(C)C
• Canonical SMILES: CCOc1cc2ncc(c(c2cc1NC(=O)/C=C/CN(C)C)Nc1ccc(c(c1)Cl)OCc1ccccn1)C#N
• InChI: InChI=1S/C30H29ClN6O3/c1-4-39-28-16-25-23(15-26(28)36-29(38)9-7-13-37(2)3)30(20(17-32)18-34-25)35-21-10-11-27(24(31)14-21)40-19-22-8-5-6-12-33-22/h5-12,14-16,18H,4,13,19H2,1-3H3,(H,34,35)(H,36,38)/b9-7+
• InChIKey: JWNPDZNEKVCWMY-VQHVLOKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-4-[bis(^2H₃)methylamino]-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)but-2-enamide
• IUPAC Traditional name: (2E)-4-[bis(^2H₃)methylamino]-N-(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-3-cyano-7-ethoxyquinolin-6-yl)but-2-enamide
• Synonyms: (2E)-N-[4-[[3-Chloro-4-(2-pyridinylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-4-(dimethylamino-d6)-2-butenamide; HKI 272-d6; Neratinib-d6

Database IDs

• PubChem SID: 164230989
• PubChem CID: 49870271

CALCULATED PROPERTIES

• Acid pKa: 12.553535
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 1.3522266
• LogD (pH = 7.4): 3.049588
• Log P: 4.469319
• Molar Refractivity: 157.2861 cm^3
• Polarizability: 60.482185 Å^3
• Polar Surface Area: 112.4 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N390092

Labelled Neratinib (N390090). An oral, irreversible dual EGFR/HER2 inhibitor for breast and non-small cell lung cancer. Antitumor agent.

REFERENCES

• Vogel, C., et al.: J. Clin. Oncol., 20, 719 (2002)
• Ji, H., et al.: Cancer Cell., 9, 485 (2002)
• Sequist, L., et al.: Oncologist, 12, 325 (2002)