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

• ChemBase ID: 178686
• Molecular Formular: C22H25FN4O2
• Molecular Mass: 396.4579032
• Monoisotopic Mass: 396.19615428
• SMILES: c1cc2c(cc1F)/C(=C/c1c(c(c([nH]1)C)C(=O)NCCN1CCCC1)C)/C(=O)N2
• Canonical SMILES: Fc1ccc2c(c1)/C(=C/c1[nH]c(c(c1C)C(=O)NCCN1CCCC1)C)/C(=O)N2
• InChI: InChI=1S/C22H25FN4O2/c1-13-19(12-17-16-11-15(23)5-6-18(16)26-21(17)28)25-14(2)20(13)22(29)24-7-10-27-8-3-4-9-27/h5-6,11-12,25H,3-4,7-10H2,1-2H3,(H,24,29)(H,26,28)/b17-12-
• InChIKey: SRSGVKWWVXWSJT-ATVHPVEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-N-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrrole-3-carboxamide
• IUPAC Traditional name: 5-{[(3Z)-5-fluoro-2-oxo-1H-indol-3-ylidene]methyl}-2,4-dimethyl-N-[2-(pyrrolidin-1-yl)ethyl]-1H-pyrrole-3-carboxamide
• Synonyms: 5-[(Z)-(5-Fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-N-[2-(1-pyrrolidinyl)ethyl]-1H-pyrrole-3-carboxamide; 5-(5-Fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid (2-(Pyrrolidin-1-yl)ethyl)amide; PHA 291639; SU 11654; ToceranibDiscontinued Pfizer Patent issues

Database IDs

• CAS Number: 356068-94-5
• PubChem SID: 164234596
• PubChem CID: 5329106

CALCULATED PROPERTIES

• Acid pKa: 11.461624
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.186452
• LogD (pH = 7.4): 1.5766504
• Log P: 2.6195583
• Molar Refractivity: 114.3101 cm^3
• Polarizability: 41.401566 Å^3
• Polar Surface Area: 77.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T525500

Toceranib is a multitargeted indolinone receptor tyrosine kinase (RTK) inhibitor. Toceranib exhibited activity against a variety of spontaneous malignancies in canine such as mast cell tumors, mixed mammary carcinomas, soft tissue sarcomas, and multiple m

REFERENCES

• London, C.A. et al.: Clin. Cancer Res., 9, 2755 (2003)
• Zavodovskaya, R. et al.: Am. J. vVt. Res., 67, 633 (2003)
• Malone, E.K. et al.: Vet. Comp. Oncol., 8, 209 (2003)