4-[4-(4-fluorophenyl)-1-(piperidin-4-yl)-1H-imidazol-5-yl]pyrimidin-2-amine trihydrochloride

• ChemBase ID: 132860
• Molecular Formular: C18H22Cl3FN6
• Molecular Mass: 447.7648832
• Monoisotopic Mass: 446.09555599
• SMILES: c1cc(ccc1c1c(n(cn1)C1CCNCC1)c1ccnc(n1)N)F.Cl.Cl.Cl
• Canonical SMILES: Nc1nccc(n1)c1n(cnc1c1ccc(cc1)F)C1CCNCC1.Cl.Cl.Cl
• InChI: InChI=1S/C18H19FN6.3ClH/c19-13-3-1-12(2-4-13)16-17(15-7-10-22-18(20)24-15)25(11-23-16)14-5-8-21-9-6-14;;;/h1-4,7,10-11,14,21H,5-6,8-9H2,(H2,20,22,24);3*1H
• InChIKey: IPFBHUGKKONHFR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[4-(4-fluorophenyl)-1-(piperidin-4-yl)-1H-imidazol-5-yl]pyrimidin-2-amine trihydrochloride
• IUPAC Traditional name: 4-[5-(4-fluorophenyl)-3-(piperidin-4-yl)imidazol-4-yl]pyrimidin-2-amine trihydrochloride
• Synonyms: 5-(2-Aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1-(4-piperidinyl)imidazole trihydrochloride; SB 220025 trihydrochloride

Database IDs

• CAS Number: 197446-75-6
• MDL Number: MFCD08705333
• PubChem SID: 24724623; 162227137
• PubChem CID: 16079013

CALCULATED PROPERTIES

• Acid pKa: 16.378748
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5171407
• LogD (pH = 7.4): -0.83588886
• Log P: 1.7774142
• Molar Refractivity: 94.9989 cm^3
• Polarizability: 37.97174 Å^3
• Polar Surface Area: 81.65 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble22 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - S9070

Biochem/physiol Actions
SB 220025 is a potent, specific inhibitor of human p38 mitogen-activated protein (MAP) kinase, with an IC50 value of 60 nM and 50- to 1000-fold selectivity. SB 220025 reduces inflammatory cytokine production and inhibits angiogenesis. SB 220025 reduced the lipopolysaccharide-induced production of TNF at an ED50 value of 7.5 mg/kg. At 30 mg/kg, SB 220025 reduced the expression of TNF and inhibited angiogenesis by ~40%. In a further study, the effects of p38/CSBP MAP kinase inhibition in angiogenesis-dependent chronic inflammatory disease was tested in murine collagen-induced arthritis and SB 220025 was able to prevent the progression of established arthritis.