6-(2,4-difluorophenoxy)-2-[(1,5-dihydroxypentan-3-yl)amino]-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

• ChemBase ID: 176213
• Molecular Formular: C19H20F2N4O4
• Molecular Mass: 406.3833064
• Monoisotopic Mass: 406.14526158
• SMILES: n1c(nc2c(c1)cc(c(=O)n2C)Oc1ccc(cc1F)F)NC(CCO)CCO
• Canonical SMILES: OCCC(Nc1ncc2c(n1)n(C)c(=O)c(c2)Oc1ccc(cc1F)F)CCO
• InChI: InChI=1S/C19H20F2N4O4/c1-25-17-11(10-22-19(24-17)23-13(4-6-26)5-7-27)8-16(18(25)28)29-15-3-2-12(20)9-14(15)21/h2-3,8-10,13,26-27H,4-7H2,1H3,(H,22,23,24)
• InChIKey: JYYLVUFNAHSSFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2,4-difluorophenoxy)-2-[(1,5-dihydroxypentan-3-yl)amino]-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one
• IUPAC Traditional name: pamapimod
• Synonyms: 6-(2,4-Difluorophenoxy)-2-[[3-hydroxy-1-(2-hydroxyethyl)propyl]amino]-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one; R 1503; Ro 4402257; Pamapimod

Database IDs

• CAS Number: 449811-01-2
• PubChem SID: 164232123
• PubChem CID: 16220188

CALCULATED PROPERTIES

• Acid pKa: 14.712303
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.9251709
• LogD (pH = 7.4): 0.9256284
• Log P: 0.92563426
• Molar Refractivity: 104.1584 cm^3
• Polarizability: 37.594147 Å^3
• Polar Surface Area: 107.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P167500

A selective inhibitor of the α-isoform of p38 MAP kinase. It is used in in treatment of patient with rheumatoid arthritis. Pamapimod was tolerable but not effective as Methotrexate.

REFERENCES

• Guan, Z., et al.: J. Biol. Chem., 273, 12901 (1998)
• Lee, J., et al.: Pharmacol. Ther., 82, 389 (1998)
• Korb, A., et al.: Arthritis Rheum., 54, 2745 (1998)