Skip to Content
Merck
All Photos(2)

Documents

Safety Information

S8307

Sigma-Aldrich

SB 203580

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

Synonym(s):

4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

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

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)

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.

Pictograms

Exclamation mark
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

S8307-IP:
S8307-1MG:
S8307-VAR:
S8307-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Harini Lakshminarasimhan et al.
Scientific reports, 7(1), 4533-4533 (2017-07-05)
Doxorubicin (DOX), a common chemotherapeutic agent, impairs synaptic plasticity. DOX also causes a persistent increase in basal neuronal excitability, which occludes serotonin-induced enhanced excitability. Therefore, we sought to characterize and reverse DOX-induced physiological changes and modulation of molecules implicated in
S Hashimoto et al.
Biochemical and biophysical research communications, 258(2), 443-447 (1999-05-18)
We examined the regulatory role of a reduction/oxidation (redox) control protein, thioredoxin (TRX), in tumor necrosis factor-alpha (TNF-alpha)-induced p38 MAP kinase activation and p38 MAP kinase-mediated cytokine expression utilizing TRX-transfected murine L929 cells (TRX14). The results showed that TNF-alpha-induced p38
C A Hall-Jackson et al.
Oncogene, 18(12), 2047-2054 (1999-05-13)
The inhibition of SAPK2a/p38 (a mitogen activated protein (MAP) kinase family member) by SB 203580 depends on the presence of threonine at residue 106. Nearly all other protein kinases are insensitive to this drug because a more bulky residue occupies
Camille Robinet et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 30(2), 286-298 (2009-10-02)
MCT2 is the predominant neuronal monocarboxylate transporter allowing lactate use as an alternative energy substrate. It is suggested that MCT2 is upregulated to meet enhanced energy demands after modifications in synaptic transmission. Brain-derived neurotrophic factor (BDNF), a promoter of synaptic
Rosalina Villalon Landeros et al.
The Journal of physiology, 595(14), 4663-4676 (2017-04-25)
The catechol metabolites of 17β-oestradiol (E Previously we demonstrated that the biologically active metabolites of 17β-oestradiol, 2-hydroxyoestradiol (2-OHE
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service