Millipore Sigma Vibrant Logo
Attention: We have moved. Merck Millipore products are no longer available for purchase on MerckMillipore.com.Learn More

559389 SB 203580 - CAS 152121-47-6 - Calbiochem

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).

SB 203580 - CAS 152121-47-6 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)1H-imidazole, p38 MAP Kinase Inhibitor XVI

Primary Target: P38MAPK
View Products on Sigmaaldrich.com
559389
Purchase on Sigma-Aldrich

Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
152121-47-6C₂₁H₁₆N₃OSF

Products

Catalogue NumberPackaging Qty/Pack
559389-10MG Glass bottle 10 mg
559389-1MG Plastic ampoule 1 mg
559389-5MG Glass bottle 5 mg
Description
OverviewReduces 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.
Catalogue Number559389
Brand Family Calbiochem®
Synonyms4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)1H-imidazole, p38 MAP Kinase Inhibitor XVI
References
ReferencesYamada. 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.
Product Information
CAS number152121-47-6
ATP CompetitiveY
FormThin film
Hill FormulaC₂₁H₁₆N₃OSF
Chemical formulaC₂₁H₁₆N₃OSF
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
ApplicationSB 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).
Biological Information
Primary TargetP38MAPK
Primary Target IC<sub>50</sub>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
Purity≥98% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
R PhraseR: 36/37/38

Irritating to eyes, respiratory system and skin.
S PhraseS: 26-36-45

In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Wear suitable protective clothing.
In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Irritant
Storage -20°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Packaging Information
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
559389-10MG 04055977192490
559389-1MG 07790788051532
559389-5MG 04055977192537

Documentation

SB 203580 - CAS 152121-47-6 - Calbiochem SDS

Title

Safety Data Sheet (SDS) 

SB 203580 - CAS 152121-47-6 - Calbiochem Certificates of Analysis

TitleLot Number
559389

References

Reference overview
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.

Data Sheet

Title
Reprogramming Cell Fate and Function Novel Strategies for iPSC Generation, Characterization, and Differentiation

Posters

Title
Human Kinome & InhibitorSelect™ Libraries

Citations

Title
  • Yamada. T., et al. 2012. Free Radic. Biol. Med. (In press)
  • Satoshi Fukumoto, et al. (2006) Laminin 5 is required for dental epithelium growth and polarity and the development of tooth bud and shape. Journal of Biological Chemistry 281, 5008-5016.
  • Alexandra Thiel, et al. (2006) Expression of Cyclooxygenase-2 Is Regulated by Glycogen Synthase Kinase-3beta in Gastric Cancer Cells. Journal of Biological Chemistry 281, 4564-4569.
  • Anthony R. White, et al. (2006) Degradation of the alzheimer disease amyloid -peptide by metal-dependent up-regulation of metalloprotease activity. journal of Biological Chemistry 281, 17670-17680.
  • Bysani Chandrasekar, et al. (2005) The pro-atherogenic cytokine interleukin-18 induces CXCL16 expression in rat aortic smooth muscle cells via MyD88, interleukin-1 receptor-associated kinase, tumor necrosis factor receptor-associated factor 6, c-Src, phosphatidylinositol 3-kinase, Akt, c-J. Journal of Biological Chemistry 280, 26263-26277.
  • Guadalupe Sabio, et al. (2005) p38γ regulates the localisation of SAP97 in the cytoskeleton by modulating its interaction with GKAP. The EMBO Journal 24, 1134-1145.
  • Jose G. Trevino, et al. (2005) Expression and activity of Src regulate interleukin-8 expression in pancreatic adenocarcinoma cells: implications for angiogenesis. Cancer Research 65, 7214-7222.
  • Wojciech Wojciechowski, et al. (2005) Enhanced Expression of CD20 in Human Tumor B Cells is Controlled Through ERK-Dependent Mechanisms. Journal of Immunology 174, 7859-7868.
  • Yung-Luen Yu, et al. (2005) MAP kinase-mediated phosphorylation of GATA-1 promotes Bcl-XL expression and cell survival. Journal of Biological Chemistry 280, 29533-29542.
  • Naoto Inukai, et al. (2004) A novel hydrogen peroxide-induced phosphorylation and ubiquitination pathway leading to RNA polymerase II proteolysis. Journal of Biological Chemistry 279, 8190-8195.
    		•
    Data Sheet

    Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

    Revision28-February-2012 RFH
    Synonyms4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)1H-imidazole, p38 MAP Kinase Inhibitor XVI
    DescriptionReduces 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.
    FormThin film
    CAS number152121-47-6
    Chemical formulaC₂₁H₁₆N₃OSF
    Structure formulaStructure formula
    Purity≥98% by HPLC
    SolubilityDMSO (30 mg/ml)
    Storage Protect from light
    -20°C
    Do Not Freeze Ok to freeze
    Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
    Toxicity Irritant
    ReferencesYamada. 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.
    Citation
  • Yamada. T., et al. 2012. Free Radic. Biol. Med. (In press)
  • Satoshi Fukumoto, et al. (2006) Laminin 5 is required for dental epithelium growth and polarity and the development of tooth bud and shape. Journal of Biological Chemistry 281, 5008-5016.
  • Alexandra Thiel, et al. (2006) Expression of Cyclooxygenase-2 Is Regulated by Glycogen Synthase Kinase-3beta in Gastric Cancer Cells. Journal of Biological Chemistry 281, 4564-4569.
  • Anthony R. White, et al. (2006) Degradation of the alzheimer disease amyloid -peptide by metal-dependent up-regulation of metalloprotease activity. journal of Biological Chemistry 281, 17670-17680.
  • Bysani Chandrasekar, et al. (2005) The pro-atherogenic cytokine interleukin-18 induces CXCL16 expression in rat aortic smooth muscle cells via MyD88, interleukin-1 receptor-associated kinase, tumor necrosis factor receptor-associated factor 6, c-Src, phosphatidylinositol 3-kinase, Akt, c-J. Journal of Biological Chemistry 280, 26263-26277.
  • Guadalupe Sabio, et al. (2005) p38γ regulates the localisation of SAP97 in the cytoskeleton by modulating its interaction with GKAP. The EMBO Journal 24, 1134-1145.
  • Jose G. Trevino, et al. (2005) Expression and activity of Src regulate interleukin-8 expression in pancreatic adenocarcinoma cells: implications for angiogenesis. Cancer Research 65, 7214-7222.
  • Wojciech Wojciechowski, et al. (2005) Enhanced Expression of CD20 in Human Tumor B Cells is Controlled Through ERK-Dependent Mechanisms. Journal of Immunology 174, 7859-7868.
  • Yung-Luen Yu, et al. (2005) MAP kinase-mediated phosphorylation of GATA-1 promotes Bcl-XL expression and cell survival. Journal of Biological Chemistry 280, 29533-29542.
  • Naoto Inukai, et al. (2004) A novel hydrogen peroxide-induced phosphorylation and ubiquitination pathway leading to RNA polymerase II proteolysis. Journal of Biological Chemistry 279, 8190-8195.
    		•

    Related Products & Applications

    Alternative Products

    Catalogue Number Description
    559395 SB 203580, Hydrochloride - CAS 869185-85-3 - Calbiochem
    559400 SB 203580, Iodo- - CAS 189319-35-5 - Calbiochem

    Related Products

    Catalogue Number Description
    559387 SB 202474 - CAS 172747-50-1 - Calbiochem
    559388 SB 202190 - CAS 152121-30-7 - Calbiochem
    559396 SB 220025

    Categories

    Life Science Research > Inhibitors and Biochemicals > Small Molecules & Inhibitors > Protein Phosphorylation / Dephosphorylation > MAP Kinase Inhibitors