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

• ChemBase ID: 179720
• Molecular Formular: C26H33FN4O7
• Molecular Mass: 532.5612232
• Monoisotopic Mass: 532.23332764
• SMILES: c1(c([nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(cc2)F)C)C(=O)NCCN(CC)CC.C(C(=O)O)C(C(=O)O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)O.CCN(CCNC(=O)c1c(C)[nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(F)cc2)CC
• InChI: InChI=1S/C22H27FN4O2.C4H6O5/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;5-2(4(8)9)1-3(6)7/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28);2,5H,1H2,(H,6,7)(H,8,9)/b17-12-
• InChIKey: LBWFXVZLPYTWQI-HBPAQXCTSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 341031-54-7
• PubChem SID: 164235630
• PubChem CID: 44181971

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: 42.123272 Å^3
• Polar Surface Area: 77.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Multi-targeted receptor tyrosine kinase (RTK) inhibitor

Product Information

• Salt Data: Malate
• Application(s): Anticancer drug for the treatment of renal cell carcinoma (RCC) and imatinib-resistant gastrointestinal stromal tumor (GIST)

REFERENCES

• Motzer RJ et al. (2007). "Sunitinib versus interferon alfa in metastatic renal-cell carcinoma". N Engl J Med 356 (2): 115?24
• Motzer RJ et al. "Phase 3 Randomized Trial of Sunitinib malate (SU11248) versus Interferon-alfa as First-line Systemic Therapy for Patients with Metastatic Renal Cell Carcinoma".
• Presented at ASCO 2006
• Demetri GD et al. (2006). "Efficacy and safety of sunitinib in patients with advanced gastrointestinal stromal tumour after failure of imatinib: a randomised controlled trial". Lancet 368: 1329?338
• Miller KD et al.. "Phase II study of SU11248, a multi-targeted tyrosine kinase inhibitor in patients with previously treated metastatic breast cancer".