S8307

SB 203580

≥98% (HPLC), solid, p38 MAPK inhibitor

• Synonym(s): 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole
• Empirical Formula (Hill Notation): C₂₁H₁₆FN₃OS
• CAS Number: 152121-47-6
• Molecular Weight: 377.43
• MDL number: MFCD00922198
• UNSPSC Code: 12352200
• PubChem Substance ID: 24899788
• NACRES: NA.77

Properties

• product name: SB 203580, solid, ≥98% (HPLC)
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: solid
• color: white to off-white
• solubility: DMSO: ≥20 mg/mL
• storage temp.: −20°C
• SMILES string: CS(=O)c1ccc(cc1)-c2nc(-c3ccc(F)cc3)c([nH]2)-c4ccncc4
• 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
• Gene Information: human ... CYP1A2(1544) , CYP2C19(1557) , CYP2C9(1559) , CYP2D6(1565) , CYP3A4(1576) , IL1B(3553) , MAPK14(1432) , MAPK8IP2(23542) , RAF1(5894) , TNF(7124)

Description

Application

MDCK cells were treated with SB 203580 to study the role of MAPK signaling in inducing hypertonicity of cell membrane and potassium depletion.¹⁶ It was used to inhibit MAPK signaling in mouse cortical neurons¹⁷ and human hepatocellular carcinoma cell lines.¹⁸

Biochem/physiol Actions

SB 203580 is a pyridinyl imidazole that suppresses the activation of MAPKAP kinase-2 and inhibits the phosphorylation of heat shock protein (HSP) 27 in response to IL-1, cellular stresses and bacterial endotoxin in vivo. It does not inhibit JNK or p42 MAP kinase and therefore, is useful for studying the physiological roles and targets of p38 MAPK and MAPKAP kinase-2. It has been shown to induce the activation of the serine/threonine kinase Raf-1 and has been reported to inhibit cytokine production.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the MAPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves