| Identification | More | [Name]
SB 203580 | [CAS]
152121-47-6 | [Synonyms]
CS-42
SB SB
SB 203580
PB 203580
RWJ 64809
SB 2035850
SB 203580, >=98%
SB203580;SB 203580
SB 203580USP/EP/BP
SB203580(RWJ 64809)
RWJ 64809; PB 203580
SB 203580 hydrochlor
SB 203580 HYDROCHLORIDE
MAPK inhibitor (SB 203580)
RWJ 64809;PB 203580;SB203580;SB-203580
SB 203580 - CAS 152121-47-6 - Calbiochem
SB203580 (RWJ 64809, PB 203580)
4-(4-FLUOROPHENYL)-2-(4-METHYLSULFINYLPHENYL)-5-(4-PYRIDYL) 1H-IMIDAZOLE
4-(4'-Fluorophenyl)-2-(4'-methylsulphinylphenyl)-5-(4'-pyridyl)imidazole
4-[5-(4-FLUOROPHENYL)-2-(4-METHYLSULFINYLPHENYL)-3H-IMIDAZOL-4-YL]PYRIDINE
4-[5-(4-FLUOROPHENYL)-2-[4-(METHYLSULFONYL)PHENYL]-1H-IMIDAZOL-4-YL]PYRIDINE
4-(4-FLUOROPHENYL)-2-(4-METHYLSULFINYLPHENYL)-5-(4-PYRIDYL)1H-IMIDAZOLE, HCL
4-[4-(4-Fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl]pyridine
4-[5-(4-fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-4-yl]pyridine
Pyridine, 4-[4-(4-fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl]-
4-[5-(4-FLUOROPHENYL)-2-[4-(METHYLSULPHONYL)PHENYL]-1H-IMIDAZOL-4-YL]PYRIDINE HYDROCHLORIDE
4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole SB 203580
SB 203580 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole | [Molecular Formula]
C21H16FN3OS | [MDL Number]
MFCD00922198 | [Molecular Weight]
377.43 | [MOL File]
152121-47-6.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Solid | [Melting point ]
144-146 | [Boiling point ]
615.6±55.0 °C(Predicted) | [density ]
1.4 | [storage temp. ]
−20°C
| [solubility ]
DMSO: 50 mg/mL
| [form ]
solid
| [pka]
9.60±0.10(Predicted) | [color ]
white to off-white
| [Usage]
A pyridinyl imidazole which acts as a specific inhibitor of p38 MAP kinase. Does not inhibit the MAP kinase homologs JNK and p42 MAP kinase | [Stability:]
-200C | [InChI]
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) | [InChIKey]
CDMGBJANTYXAIV-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(C2NC(C3=CC=C(S(C)=O)C=C3)=NC=2C2=CC=C(F)C=C2)=C1 | [CAS DataBase Reference]
152121-47-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Description]
SB 203580 (152121-47-6) is a potent and selective inhibitor of p38 MAP kinase, IC50=50 and 500 nM for p38 and p38β2 respectively.1 No other kinases (in a panel of 30) were significantly inhibited including p38γ and δ at 10 μM.2?A potent inhibitor of inflammatory cytokine production (IC50=15-25 mg/kg in mice and rats) in animal models of arthritis, bone resorption, endotoxin shock and immune function.3 | [Chemical Properties]
White to Off-White Solid | [Uses]
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 | [Uses]
A p38 MAPK inhibitor with an IC50 range of 0.3-0.5 μM and blocks PKB phosphorylation with an IC50 range of 3-5 μM. | [Uses]
A pyridinyl imidazole which acts as a specific inhibitor of p38 MAP kinase. Does not inhibit the MAP kinase homologs JNK and p42 MAP kinase | [Definition]
ChEBI: A member of the class of imidazoles carrying 4-methylsulfinylphenyl, 4-pyridyl and 4-fluorophenyl substituents at positions 2, 4 and 5 respectively. An inhibitor of mitogen-activated protein kinase. | [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 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. | [Biological Activity]
Water-soluble salt of SB 203580 (4-[5-(4-Fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]pyridine ). Selective inhibitor of p38 mitogen-activated protein kinase (IC 50 values are 50 and 500 nM for SAPK2a/p38 and SAPK2b/p38 β 2 respectively). Displays 100-500-fold selectivity over LCK, GSK3 β and PKB α . Shown to inhibit interleukin-2-induced T-cell proliferation, cyclooxygenase-1 and -2, and thromboxane synthase. | [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. | [storage]
Desiccate at 4°C | [References]
1) Cuenda et al. (1995), SB 203580 is a specific inhibitor of a MAP kinase homologue which is stimulated by cellular stresses and interleukin-1; FEBS Lett., 364 229
2) Davies et al. (2000), Specificity and mechanism of action of some commonly used protein kinase inhibitors; Biochem. J., 351 95
3) Badger et al. (1996), Pharmacological profile of SB 203580, a selective inhibitor of cytokine suppressive binding protein/p38 kinase, in animal models of arthritis, bone resorption, endotoxin shock and immune function; Pharmacol. Exp. Ther. 279 1453 |
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