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

• ChemBase ID: 165858
• Molecular Formular: C20H23FN4O2
• Molecular Mass: 370.4206232
• Monoisotopic Mass: 370.18050422
• SMILES: c1cc2c(cc1F)/C(=C/c1c(c(c([nH]1)C)C(=O)NCCNCC)C)/C(=O)N2
• Canonical SMILES: CCNCCNC(=O)c1c(C)[nH]c(c1C)/C=C/1\C(=O)Nc2c1cc(F)cc2
• InChI: InChI=1S/C20H23FN4O2/c1-4-22-7-8-23-20(27)18-11(2)17(24-12(18)3)10-15-14-9-13(21)5-6-16(14)25-19(15)26/h5-6,9-10,22,24H,4,7-8H2,1-3H3,(H,23,27)(H,25,26)/b15-10-
• InChIKey: LIZNIAKSBJKPQC-GDNBJRDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(ethylamino)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-(ethylamino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide
• Synonyms: N-[2-(Ethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide; N-Desethyl Sunitinib

Database IDs

• CAS Number: 356068-97-8
• PubChem SID: 162259991
• PubChem CID: 10292573

CALCULATED PROPERTIES

• Acid pKa: 11.467982
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -1.0046563
• LogD (pH = 7.4): -0.028904572
• Log P: 2.0469453
• Molar Refractivity: 106.223 cm^3
• Polarizability: 38.450085 Å^3
• Polar Surface Area: 86.02 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Yellow Solid
• Melting Point: 244-246°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D289650

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)