559389

SB 203580

SB 203580, CAS 152121-47-6, is a highly specific, potent, cell-permeable, selective, reversible, and ATP-competitive inhibitor of p38 MAP kinase (IC₅₀ = 34 nM in vitro, 600 nM in cells).

• Synonym(s): SB 203580, 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)1H-imidazole, p38 MAP Kinase Inhibitor XVI
• Empirical Formula (Hill Notation): C₂₁H₁₆FN₃OS
• CAS Number: 152121-47-6
• Molecular Weight: 377.43
• MDL number: MFCD00922198
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: film (Thin)
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• solubility: DMSO: 30 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C21H16FN3OS/c1-27(26)18-8-4-16(5-9-18)21-24-19(14-2-6-17(22)7-3-14)20(25-21)15-10-12-23-13-11-15/h2-13H,1H3,(H,24,25)
• InChI key: CDMGBJANTYXAIV-UHFFFAOYSA-N

Description

General description

Reduces epirubicin-induced cell injury and caspase-3/7 activity. A highly specific, potent, cell-permeable, selective, reversible, and ATP-competitive inhibitor of p38 MAP kinase (IC₅₀ = 34 nM in vitro, 600 nM in cells). Does not significantly inhibit the JNK and p42 MAP kinase at 100 µM. Inhibits IL-1 and TNF-α production from LPS-stimulated human monocytes and the human monocyte cell line THP-1 (IC₅₀ = 50-100 nM). Inhibits bone morphogenetic protein-2-induced neurite outgrowth in PC12 cells. Also inhibits platelet aggregation caused by collagen (IC₅₀ = 0.2-1.0 µM) or the thromboxane analog U-46619 (Cat. No. 538944). A 1 mg/ml solution of SB 203580 (Cat. No. 559398) in anhydrous DMSO is also available.

Reduces epirubicin-induced cell injury and caspase-3/7 activity. A highly specific, potent, cell-permeable, selective, reversible, and ATP-competitive inhibitor of p38 kinase (IC₅₀ = 34 nM in vitro, 600 nM in cells). Also known as reactivating kinase (RK) and CSBP (cytokine synthesis anti-inflammatory drug binding protein). Does not significantly inhibit JNK or p42 MAP kinase even at 100 µM. Inhibits IL-1 and TNF-α production from LPS-stimulated human monocytes and the human monocyte cell line THP-1 (IC₅₀ = 50-100 nM). SB 203580 has also been shown to be an effective inhibitor of inflammatory cytokine production in vivo in both mice and rats.

Biochem/physiol Actions

Cell permeable: yes

Product competes with ATP.

Reversible: yes

Target IC₅₀: 34 nM against p38 MAP kinase in vitro, 600 nM in cells; 50-100 nM against IL-1 and TNF-α production from LPS-stimulated human monocytes and the human monocyte cell line THP-1; 0.2-1.0 µM against platelet aggregation caused by collagen

Warning

Toxicity: Irritant (B)

Other Notes

Yamada. T., et al. 2012. Free Radic. Biol. Med. (In press)
Powell, D.J., et al. 2003. Mol. Cell Biol.23, 7794.
Davies, S.P., et al. 2000. Biochem. J.351, 95.
Iwasaki, S., et al. 1999. J. Biol. Chem.274, 26503.
Gallagher, T.F., et al. 1997. Bioorg. Med. Chem. 5, 49.
LoGrasso, P.V., et al. 1997. Biochem. 36, 10422.
Hazzalin, C.A., et al. 1996. Curr. Biol.6, 1028.
Kramer, R.M., et al. 1996. J. Biol. Chem.271, 27723.
Saklatvala, J., et al. 1996. J. Biol. Chem. 271, 6586.
Cuenda, A., et al. 1995. FEBS Lett.364, 229.
Gallagher, T.F., et al. 1995. Bioorg. Med. Chem. Lett. 5, 1171.
Lee, J.C., et al. 1994. Nature 372, 739.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable