N-[2-(diethylamino)(2H4)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide

• ChemBase ID: 178036
• Molecular Formular: C22H27FN4O2
• Molecular Mass: 398.4737832
• Monoisotopic Mass: 398.21180434
• SMILES: c1cc2c(cc1F)/C(=C/c1c(c(c([nH]1)C)C(=O)NCCN(CC)CC)C)/C(=O)N2
• Canonical SMILES: CCN(CCNC(=O)c1c(C)[nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(F)cc2)CC
• InChI: InChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
• InChIKey: WINHZLLDWRZWRT-ATVHPVEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(diethylamino)(^2H₄)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide
• IUPAC Traditional name: N-[2-(diethylamino)(^2H₄)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide
• Synonyms: N-[2-Diethylamino(ethyl-d4)]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide; Sutent-d4; SU-11248-d4; Sunitinib-d4

Database IDs

• PubChem SID: 164233946
• PubChem CID: 25214490

CALCULATED PROPERTIES

• Acid pKa: 11.462899
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.2940416
• LogD (pH = 7.4): 1.2792807
• Log P: 2.9273767
• Molar Refractivity: 116.2663 cm^3
• Polarizability: 42.123337 Å^3
• Polar Surface Area: 77.23 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S820003

Labelled Sunitinib (S820000), a multi-kinase inhibitor targeting several receptor tyrosine kinases (RTK).

REFERENCES

• Sun, L., et al.: J. Med. Chem., 46, 1116 (2003)
• Mendel, D.B., et al.: Clin. Cancer Res., 9, 327 (2003)
• Sistla, A., et al.: Drug Dev. Ind. Pharm., 30, 19 (2003)
• Sakamoto, K.M., et al.: Curr. Opin. Invest. Drugs, 5. 1329 (2003)