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

• ChemBase ID: 167228
• Molecular Formular: C18H20ClFN4O2
• Molecular Mass: 378.8284032
• Monoisotopic Mass: 378.1258818
• SMILES: Cl.c1cc2c(cc1F)/C(=C/c1c(c(c([nH]1)C)C(=O)NCCN)C)/C(=O)N2
• Canonical SMILES: NCCNC(=O)c1c(C)[nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(F)cc2.Cl
• InChI: InChI=1S/C18H19FN4O2.ClH/c1-9-15(22-10(2)16(9)18(25)21-6-5-20)8-13-12-7-11(19)3-4-14(12)23-17(13)24;/h3-4,7-8,22H,5-6,20H2,1-2H3,(H,21,25)(H,23,24);1H/b13-8-
• InChIKey: NDLBSVCHUWKNAB-MGAWDJABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-aminoethyl)-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide hydrochloride
• IUPAC Traditional name: N-(2-aminoethyl)-5-{[(3Z)-5-fluoro-2-oxo-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide hydrochloride
• Synonyms: N-(2-Aminoethyl)-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide Hydrochloride; N,N-Didesethyl Sunitinib Hydrochloride

Database IDs

• CAS Number: 1217216-61-9
• PubChem SID: 162261361
• PubChem CID: 46781265

CALCULATED PROPERTIES

• Acid pKa: 11.463418
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -1.5435829
• LogD (pH = 7.4): -0.34956837
• Log P: 1.3981326
• Molar Refractivity: 96.6998 cm^3
• Polarizability: 34.780613 Å^3
• Polar Surface Area: 100.01 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Yellow Solid
• Melting Point: >280°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D440965

A metabolite of Sunitinib (S820000).

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)