Millipore Sigma Vibrant Logo

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 This Product on Sigma-Aldrich
559389
View Pricing & Availability

Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
152121-47-6C₂₁H₁₆N₃OSF

Pricing & Availability

Catalogue Number AvailabilityPackaging Qty/Pack Price Quantity
559389-10MGCN
Retrieving availability...
—
Limited Availability Limited Availability
In Stock 
Discontinued
Limited Quantities Available
Availability to be confirmed
    Remaining : Will advise
      Remaining : Will advise
      Will advise
      Contact Customer Service
      Contact Customer Service

      		 Glass bottle 10 mg
      Retrieving price...
      Price could not be retrieved
      Minimum Quantity is a multiple of
      Maximum Quantity is
      Upon Order Completion More Information
      You Saved ()
       
      —
      Request Pricing
      		 —
      559389-1MGCN
      Retrieving availability...
      —
      Limited Availability Limited Availability
      In Stock 
      Discontinued
      Limited Quantities Available
      Availability to be confirmed
        Remaining : Will advise
          Remaining : Will advise
          Will advise
          Contact Customer Service
          Contact Customer Service

          		 Plastic ampoule 1 mg
          Retrieving price...
          Price could not be retrieved
          Minimum Quantity is a multiple of
          Maximum Quantity is
          Upon Order Completion More Information
          You Saved ()
           
          —
          Request Pricing
          		 —
          559389-5MGCN
          Retrieving availability...
          —
          Limited Availability Limited Availability
          In Stock 
          Discontinued
          Limited Quantities Available
          Availability to be confirmed
            Remaining : Will advise
              Remaining : Will advise
              Will advise
              Contact Customer Service
              Contact Customer Service

              		 Glass bottle 5 mg
              Retrieving price...
              Price could not be retrieved
              Minimum Quantity is a multiple of
              Maximum Quantity is
              Upon Order Completion More Information
              You Saved ()
               
              —
              Request Pricing
              		 —
              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
              559389-10MGCN 04055977192490
              559389-1MGCN 07790788051532
              559389-5MGCN 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 Show Pricing & Availability

              Related Products

              Catalogue Number Description  
              559388 SB 202190 - CAS 152121-30-7 - Calbiochem Show Pricing & Availability
              559396 SB 220025 Show Pricing & Availability

              Categories

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