ChemicalBook > CAS DataBase List > SB 203580

SB 203580

Product Name
SB 203580
CAS No.
152121-47-6
Chemical Name
SB 203580
Synonyms
CS-42;SB SB;SB 2358;SB203850;PB 203580;RWJ 64809;SB 203580;SB 2035850;Adezmapimod;SB 203580, >=98%
CBNumber
CB1680333
Molecular Formula
C21H16FN3OS
Formula Weight
377.43
MOL File
152121-47-6.mol
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SB 203580 Property

Melting point:
144-146
Boiling point:
615.6±55.0 °C(Predicted)
Density 
1.4
storage temp. 
-20°C
solubility 
DMSO: 50 mg/mL
pka
9.60±0.10(Predicted)
form 
solid
color 
white to off-white
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)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-41
Safety Statements 
26-39
WGK Germany 
3
HS Code 
29333990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
559389
Product name
SB 203580
Packaging
1mg
Price
$186
Updated
2025/07/31
Sigma-Aldrich
Product number
559398
Product name
SB 203580
Purity
InSolution, ≥98%, 1 mg/ml, reversible inhibitor of p38 MAP kinase
Packaging
1ml
Price
$189
Updated
2025/07/31
Sigma-Aldrich
Product number
559389
Product name
SB 203580
Packaging
5mg
Price
$327
Updated
2025/07/31
TCI Chemical
Product number
F0864
Product name
SB 203580
Packaging
25MG
Price
$100
Updated
2025/07/31
TCI Chemical
Product number
F0864
Product name
SB 203580
Packaging
100MG
Price
$308
Updated
2025/07/31
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SB 203580 Chemical Properties,Usage,Production

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

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

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

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

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

+4°C (desiccate)

References

[1] ANA CUENDA . SB 203580 is a specific inhibitor of a MAP kinase homologue which is stimulated by cellular stresses and interleukin-1[J]. FEBS Letters, 1995, 364 2: Pages 229-233. DOI:10.1016/0014-5793(95)00357-f
[2] S. DAVIES. Specificity and mechanism of action of some commonly used protein kinase inhibitors.[J]. The Ukrainian Biochemical Journal, 2000, 24 1: 95-105. DOI:10.1042/bj3510095
[3] A M BADGER. 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.[J]. Journal of Pharmacology and Experimental Therapeutics, 1996, 279 3: 1453-1461.

SB 203580 Preparation Products And Raw materials

Raw materials

Preparation Products

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SB 203580 Suppliers

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VDM Biochemicals
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View Lastest Price from SB 203580 manufacturers

Career Henan Chemical Co
Product
SB 203580 152121-47-6
Price
US $3.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100KG
Release date
2020-01-29

152121-47-6, SB 203580Related Search:

SB 203580 (hydrochloride) SB242235 2-(5-Benzo[1,3]dioxol-5-yl-2-tert-butyl-3H-imidazol-4-yl)-6-methylpyridine hydrate hydrochloride Ispinesib U0126-EtOH MK-2206 2HCl 1,9-Pyrazoloanthrone PD 98059 SCH772984 SB-705498 4'-CHLORO-3-METHOXYCINNAMANILIDE 6-[2-tert-Butyl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-4-yl]-quinoxaline SB1317 SB 269970 HYDROCHLORIDE 5-[2-[4-[2-(Dimethylamino)ethoxy]phenyl]-5-(4-pyridinyl)-1H-imidazol-4-yl]-2,3-dihydro-1H-inden-1-one oxime SB 431542 SB 202190 LY 294002 Hydrochloride

  • SB 203580 HYDROCHLORIDE
  • MAPK inhibitor (SB 203580)
  • SB203580(RWJ 64809)
  • SB 2035850
  • 4-(4-FLUOROPHENYL)-2-(4-METHYLSULFINYLPHENYL)-5-(4-PYRIDYL) 1H-IMIDAZOLE
  • 4-(4-FLUOROPHENYL)-2-(4-METHYLSULFINYLPHENYL)-5-(4-PYRIDYL)1H-IMIDAZOLE, HCL
  • 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-[5-(4-FLUOROPHENYL)-2-[4-(METHYLSULPHONYL)PHENYL]-1H-IMIDAZOL-4-YL]PYRIDINE HYDROCHLORIDE
  • 4-[5-(4-fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-4-yl]pyridine
  • 4-[4-(4-Fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl]pyridine
  • PB 203580
  • Pyridine, 4-[4-(4-fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl]-
  • 4-(4'-Fluorophenyl)-2-(4'-methylsulphinylphenyl)-5-(4'-pyridyl)imidazole
  • SB 203580, >=98%
  • 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
  • RWJ 64809
  • RWJ 64809; PB 203580
  • SB 203580
  • SB 203580 - CAS 152121-47-6 - Calbiochem
  • SB203580;SB 203580
  • SB203580 (RWJ 64809, PB 203580)
  • CS-42
  • RWJ 64809;PB 203580;SB203580;SB-203580
  • SB SB
  • SB 203580USP/EP/BP
  • SB 203580 hydrochlor
  • Adezmapimod
  • SB 203580, ≥98% (HPLC)
  • SB203850
  • Adezmapimod (SB203580
  • Inhibitor,SB-203580,PKBα,RWJ64809,inhibit,SAPK2a,GSK3β,Mitophagy,SB 203580,p38 MAPK,Mitochondrial Autophagy,Autophagy,LCK,RWJ-64809,Adezmapimod,SAPK2b,ATP-competitive
  • SB 203580 (DMSO solution), p38 MAPK inhibitor
  • SB 203580, p38 MAPK inhibitor
  • Adezmapimod, 10 mM in DMSO
  • SB 2358
  • Adezmapimod (Synonyms: SB 203580
  • 152121-47-6
  • C21H16FN3OSHCl
  • C21H16FN3OS
  • Cell Signaling and Neuroscience
  • Cell Biology
  • BioChemical
  • Kinase/Phosphatase Biology
  • MAPK-Activated Protein Kinase (MAPKAP Kinase)
  • Serine/Threonine Kinase Inhibitors
  • Inhibitors
  • Selective inhibitor of p38 mitogen-activated protein kinase.
  • inhibitor
  • Signalling
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Protein Kinase
  • pharmacetical