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Home > Products > Pharmaceutical R&D Materials > Heterocyclic Building Blocks > 4-(4-(4-FLUOROPHENYL)-2-(4-(METHYLSULFINYL)PHENYL)-1H-IMIDAZOL-5-YL)PYRIDINE
4-(4-(4-FLUOROPHENYL)-2-(4-(METHYLSULFINYL)PHENYL)-1H-IMIDAZOL-5-YL)PYRIDINE structure, CAS 152121-47-6

4-(4-(4-FLUOROPHENYL)-2-(4-(METHYLSULFINYL)PHENYL)-1H-IMIDAZOL-5-YL)PYRIDINE

CAS Number152121-47-6

SynonymsPB 203580; 4-(4-(4-fluorophenyl)-2-(4-(methylsulfinyl)phenyl)-1H-imidazol-5-yl)pyridine; RWJ 64809; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)1H-imidazole; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(pyridin-4-yl)imidazole; 4-(4-Fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-5-(4-pyridyl)-1H-imidazole; MFCD00922198; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole; 4-{4-(4-Fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl}pyridine; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(pyridin-4-yl)-1H-imidazole; Pyridine,4-(5-(4-fluorophenyl)-2-(4-(methylsulfinyl)phenyl)-1H-imidazol-4-yl); SB 203580; SB203580; SB-203580

Molecular FormulaC21H16FN3OS

Molecular Weight377.43

Purity≥98 (HPLC)%

Density1.4±0.1 g/cm3

Boiling Point615.6±55.0 °C at 760 mmHg

Melting Point249 - 250ºC

Flash Point

Appearancesolid

EINECS0

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Cat. No.: 2A-0135015 Purity: ≥98 (HPLC)%
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Quality Control of [ 152121-47-6 ] Purity: ≥98 (HPLC)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number152121-47-6
Catalog No.2A-0135015
Chinese Name4-(4-氟苯基)-2-(4-甲基亚磺酰基苯基)-5-(4-吡啶基)-1H-咪唑
SynonymsPB 203580; 4-(4-(4-fluorophenyl)-2-(4-(methylsulfinyl)phenyl)-1H-imidazol-5-yl)pyridine; RWJ 64809; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)1H-imidazole; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(pyridin-4-yl)imidazole; 4-(4-Fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-5-(4-pyridyl)-1H-imidazole; MFCD00922198; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(4-pyridyl)-1H-imidazole; 4-{4-(4-Fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl}pyridine; 4-(4-Fluorophenyl)-2-(4-methylsulfinylphenyl)-5-(pyridin-4-yl)-1H-imidazole; Pyridine,4-(5-(4-fluorophenyl)-2-(4-(methylsulfinyl)phenyl)-1H-imidazol-4-yl); SB 203580; SB203580; SB-203580
Molecular FormulaC21H16FN3OS
Molecular Weight377.43
Purity≥98 (HPLC)
Density1.4±0.1 g/cm3
Boiling Point615.6±55.0 °C at 760 mmHg
Melting Point249 - 250ºC
Appearancesolid
Water SolubilityDMSO: 50 mg/mL
Storage Condition−20°C
ApplicationSB 203580 is a widely used p38 MAPK inhibitor with an IC50 between 0.3-0.5μM. 100-fold more selective for p38 MAPK than PKB, LCK, and GSK-3β.
EINECS0
HTC2818200000
UN(IATA)0
PubChem ID24899788
MDL NumberMFCD00922198
SMILESCS(=O)c1ccc(cc1)-c2nc(-c3ccc(F)cc3)c([nH]2)-c4ccncc4
InChI1S/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 KeyCDMGBJANTYXAIV-UHFFFAOYSA-N
NACRES CodeNA.77
UNSPSC12352200
Hazard Symbolstransportation
MSDSmsds/135015_1_152121_47_6.pdf
BioactivitySB 203580 is a widely used p38 MAPK inhibitor with an IC50 of 0.3-0.5 μM. It shows more than 100-fold selectivity over PKB, LCK, and GSK-3β. Related Catalog Signaling Pathways >> PI3K/Akt/mTOR >> Akt Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Autophagy >> Mitophagy Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Research Areas >> Inflammation/Immunology Target p38 MAP kinase:0.3-0.5 μM (IC50, in IL-2-stimulated T cells) PKB:3-5 μM (IC50, in IL-2-stimulated T cells) Autophagy Mitophagy In Vitro SB 203580 inhibits IL-2-driven T cell proliferation with an IC50 of 3-5 μM, SB 203580 is able to inhibit the activity of PDK1 in a dose-dependent manner with an IC50 in the 3-10 μM range[1]. SB 203580 at a concentration of 1 μM is sufficient for inhibiting p38 kinase activity in TF-1 cells. SB 203580 at 5 and 10 μM enhances NF-κB-mediated gene transcription independently of phosphorylation on the transactivation domains of the p65 subunit. SB 203580 at 10 μM enhances phosphorylation of ERK1/2 and JNK[1]. In Vivo All animals challenged with NS (noninfected controls) and treated with either SB203580 or placebo survive. Compared with placebo, pretreatment with the highest dose of SB203580 (100 mg/kg) 1 hour before E. coli increases the hazards ratio of death. With E. coli, compared with placebo, at 48 hours, but not 24 hours, low and high dose SB203580 decrease phosphorylated p38 MAPK and the ratio of phosphorylated to total p38. High dose SB203580 decreases lung neutrophils on histology at 24 hours in a trend approaching significance (p = 0.09) and increases them significantly at 48 hours (p = 0.01) in patterns different over time[3]. SB 203580 is evaluated in several models of cytokine inhibition and inflammatory disease. It is demonstrated clearly to be a potent inhibitor of inflammatory cytokine production in both mice and rats with IC50 values of 15 to 25 mg/kg[4]. Cell Assay Phosphorylation of p38, JNK1/2, and ERK1/2 is analysed by Western blotting. Briefly, TF-1 cells are cultured for 16 h in RPMI 1640 containing 0.1% FBS and subsequently stimulated for various periods of time with medium or OA (30 ng/mL) or SB 203580(1 μM, 5 μM, 10 μM) plus OA. After harvesting, total cell extracts are prepared by resuspending the cells in 500 μL 1× sample buffer (containing 2% SDS, 10% glycerol, 2% β-mercaptoethanol, 60 mM Tris-HCl (pH 6.8) and bromophenol blue) and lysing the cells by passing them through a 23G1 needle (three times). Cell extracts are directly boiled for 10 min and stored at -20°C. Before loading, samples are again boiled for 5 min and cell extracts are resolved by running 1/10th volume on a SDS/12.5%PAGE gel (acryla-mide:bisacrylamide is 173:1) and transferred to cellulosenitrate membrane. Immunoblotting with the antibodies is performed by standard procedures and detection is performed[2]. Animal Admin Mice[3] In survival studies, C57BL/6J mice weighing 20 g to 30 g are briefly anesthetized with isoflurane and challenged with 0.05 mL of IT normal saline (NS, noninfected controls) or E. coli (15 × 109 CFU/kg). One hour before NS challenge, mice (n = 24) receive either intraperitoneal SB203580 (100 mg/kg in 0.25 mL) or diluent only (placebo). Infected animals receive SB203580 in doses of 100, 10, 1, or 0.1 mg/kg or placebo 1 hour before IT E. coli (n = 241); SB203580 100 or 0.1 mg/kg or placebo 1 hour after E. coli (n = 121); or SB203580 100 mg/kg or placebo 12 hours after E. coli (n = 72). All animals receive ceftriaxone (100 mg/kg in 0.1 mL,subcutaneously) for 4 days and NS (0.5 mL, subcutaneously) for 1 day beginning 4 hoursafter challenge. Animals were observed every 2 hours for the initial 48 hours, every 4 hours from 48 hours to 72 hours, every 8 hours from 72 hours to 96 hours, and then twice daily until study completion (168 hours)[3]. References [1]. Lali FV, et al. The pyridinyl imidazole inhibitor SB203580 blocks phosphoinositide-dependent protein kinase activity, protein kinase B phosphorylation, and retinoblastoma hyperphosphorylation in interleukin-2-stimulated T cells independently of p38 mitogen-activated protein kinase. J Biol Chem. 2000 Mar 10;275(10):7395-402. [2]. Birkenkamp KU, et al. The p38 MAP kinase inhibitor SB203580 enhances nuclear factor-kappa B transcriptional activity by a non-specific effect upon the ERK pathway. Br J Pharmacol. 2000 Sep;131(1):99-107. [3]. Su J, et al. SB203580, a p38 inhibitor, improved cardiac function but worsened lung injury and survival during Escherichia coli pneumonia in mice. J Trauma. 2010 Jun;68(6):1317-27. [4]. Badger AM, et al. 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 Pharmacol Exp Ther. 1996 Dec;279(3):1453-61. [5]. Lin Y, et al. Critical role of astrocytic interleukin-17?A in post-stroke survival and neuronal differentiation of neural precursor cells in adult mice. Cell Death Dis. 2016 Jun 23;7(6):e2273. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 615.6±55.0 °C at 760 mmHg Melting Point 249 - 250ºC Molecular Formula C21H16FN3OS Molecular Weight 377.435 Flash Point 326.1±31.5 °C Exact Mass 377.099823 PSA 77.85000 LogP 4.10 Vapour Pressure 0.0±1.7 mmHg at 25°C Index of Refraction 1.715 InChIKey CDMGBJANTYXAIV-UHFFFAOYSA-N SMILES CS(=O)c1ccc(-c2nc(-c3ccc(F)cc3)c(-c3ccncc3)[nH]2)cc1 Storage condition −20°C Stability -200C Water Solubility DMSO: 50 mg/mL
Use ofSB 203580 is a widely used p38 MAPK inhibitor with an IC50 of 0.3-0.5 μM. It shows more than 100-fold selectivity over PKB, LCK, and GSK-3β. Properties Articles34 Name 4-[4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine Synonym More Synonyms SB203580 Biological Activity Description SB 203580 is a widely used p38 MAPK inhibitor with an IC50 of 0.3-0.5 μM. It shows more than 100-fold selectivity over PKB, LCK, and GSK-3β. Related Catalog Signaling Pathways >> PI3K/Akt/mTOR >> Akt Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Autophagy >> Mitophagy Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Research Areas >> Inflammation/Immunology p38 MAP kinase:0.3-0.5 μM (IC50, in IL-2-stimulated T cells) PKB:3-5 μM (IC50, in IL-2-stimulated T cells) References [2]. Birkenkamp KU, et al. The p38 MAP kinase inhibitor SB203580 enhances nuclear factor-kappa B transcriptional activity by a non-specific effect upon the ERK pathway. Br J Pharmacol. 2000 Sep;131(1):99-107. [3]. Su J, et al. SB203580, a p38 inhibitor, improved cardiac function but worsened lung injury and survival during Escherichia coli pneumonia in mice. J Trauma. 2010 Jun;68(6):1317-27. [4]. Badger AM, et al. 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 Pharmacol Exp Ther. 1996 Dec;279(3):1453-61. [5]. Lin Y, et al. Critical role of astrocytic interleukin-17?A in post-stroke survival and neuronal differentiation of neural precursor cells in adult mice. Cell Death Dis. 2016 Jun 23;7(6):e2273. Chemical & Physical Properties Molecular Formula C21H16FN3OS Exact Mass 377.099823 PSA 77.85000 Index of Refraction 1.715 InChIKey CDMGBJANTYXAIV-UHFFFAOYSA-N
Transport InfoShipping Name: UN
MSDS Transport InfoModule 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available
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