N-[2-chloro-6-(hydroxymethyl)phenyl]-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide

• ChemBase ID: 170789
• Molecular Formular: C22H26ClN7O3S
• Molecular Mass: 504.00494
• Monoisotopic Mass: 503.15063641
• SMILES: c1ccc(c(c1CO)NC(=O)c1cnc(s1)Nc1cc(nc(n1)C)N1CCN(CC1)CCO)Cl
• Canonical SMILES: OCCN1CCN(CC1)c1cc(nc(n1)C)Nc1ncc(s1)C(=O)Nc1c(Cl)cccc1CO
• InChI: InChI=1S/C22H26ClN7O3S/c1-14-25-18(11-19(26-14)30-7-5-29(6-8-30)9-10-31)27-22-24-12-17(34-22)21(33)28-20-15(13-32)3-2-4-16(20)23/h2-4,11-12,31-32H,5-10,13H2,1H3,(H,28,33)(H,24,25,26,27)
• InChIKey: KZNOWBHQESWSTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-chloro-6-(hydroxymethyl)phenyl]-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
• IUPAC Traditional name: N-[2-chloro-6-(hydroxymethyl)phenyl]-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide
• Synonyms: N-[2-Chloro-6-(hydroxymethyl)phenyl]-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl]amino]-5-thiazolecarboxamide; Hydroxymethyl Dasatinib

Database IDs

• CAS Number: 910297-58-4
• PubChem SID: 164226699
• PubChem CID: 11854534

CALCULATED PROPERTIES

• Acid pKa: 8.427804
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.4627687
• LogD (pH = 7.4): 2.4791167
• Log P: 2.5406919
• Molar Refractivity: 134.8509 cm^3
• Polarizability: 49.489155 Å^3
• Polar Surface Area: 126.74 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 191-195°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H946625

An oxidative metabolite of Dasatinib (M24 metabolite); used in the treatment of cancers and immune diseases.

REFERENCES

• Jaworski, T., et al.: Xenobiotica, 21, 1451 (1991)
• Shah, N., et al.: Science, 305, 399 (1991)
• O'Hare, T., et al.: Cancer Res., 65, 4500 (1991)
• Das, J., et al.: J. Med. Chem., 49, 6819 (1991)
• Christopher, L., et al.: Drug Metab. Dispos., 36, 1341 (2008