SB-202190

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H14FN3O
Molecular Weight	331.3431
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C1)C2=NC(=C(N2)C3=CC=NC=C3)C4=CC=C(F)C=C4

InChI

InChIKey=QHKYPYXTTXKZST-UHFFFAOYSA-N

InChI=1S/C20H14FN3O/c21-16-5-1-13(2-6-16)18-19(14-9-11-22-12-10-14)24-20(23-18)15-3-7-17(25)8-4-15/h1-12,25H,(H,23,24)

HIDE SMILES / InChI

Molecular Formula	C20H14FN3O
Molecular Weight	331.3431
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.selleckchem.com/products/SB-202190.html | https://www.ncbi.nlm.nih.gov/pubmed/10998351 | https://www.ncbi.nlm.nih.gov/pubmed/9632706 | https://www.ncbi.nlm.nih.gov/pubmed/11439356 | https://www.ncbi.nlm.nih.gov/pubmed/16807361 | https://www.ncbi.nlm.nih.gov/pubmed/28521467 | https://www.ncbi.nlm.nih.gov/pubmed/28542135

SB-202190 is a potent inhibitor of MAPK14 and MAPK11. It has been investigated in a number of preliminary cell-based studies including several cancer models. SB-202190 has been shown to be a UVB protectant; SB-202190 strongly inhibits UVB induced COX-2 protein expression in HaCaT cells and markedly inhibits UVB induced cox-2 mRNA. SB-202190 induces apoptosis through activation of CPP32-like caspases. SB-202190 has been studied in animal models of the Renal Fibrosis and Pemphigus Vulgaris. It should be noted that in vivo use is most effective (at least for renal fibrosis) when SB-202190 is conjugated to lysozyme using a universal linkage system.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mitogen-activated protein kinase 14 7 Target ID: Q16539\|\|\|Q8TDX0 Gene ID: 1432.0 Gene Symbol: MAPK14 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10998351	Inhibitor 8297		50.0 nM [IC50]
Mitogen-activated protein kinase 11 4 Target ID: Q15759\|\|\|Q2XNF2 Gene ID: 5600.0 Gene Symbol: MAPK11 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10998351	Inhibitor 8297		100.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11439356	Preventing	Basic research	Unknown Approved Use Unknown
Renal fibrosis 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16807361	Preventing	Preclinical	Unknown Approved Use Unknown
Pemphigus vulgaris 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16908851	Preventing	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28521467 https://www.ncbi.nlm.nih.gov/pubmed/28393288 https://www.ncbi.nlm.nih.gov/pubmed/28542135	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Signal transduction pathways involved in soluble fractalkine-induced monocytic cell adhesion.	2001 Apr 1	11264168
Role of p38 MAP kinase in diperoxovanadate-induced phospholipase D activation in endothelial cells.	2001 Aug	11435219
Inhibitors of mitogen-activated protein kinases differentially regulate eosinophil-activating cytokine release from human airway smooth muscle.	2001 Aug 15	11520738
Keratinocyte growth factor activates p38 MAPK to induce stress fibre formation in human prostate DU145 cells.	2001 Aug 30	11536048
The proto-oncoprotein Brx activates estrogen receptor beta by a p38 mitogen-activated protein kinase pathway.	2001 Dec 14	11579095
Inhibition of p38 MAPK alpha/beta reduces ischemic injury and does not block protective effects of preconditioning.	2001 Feb	11158945
Activation of Rac1 and the p38 mitogen-activated protein kinase pathway in response to all-trans-retinoic acid.	2001 Feb 9	11060298
The involvement of p38 MAPK in transforming growth factor beta1-induced apoptosis in murine hepatocytes.	2001 Jun	11453551
Signal transduction pathways involved in phosphorylation and activation of p70S6K following exposure to UVA irradiation.	2001 Jun 15	11279232
Lysophosphatidylcholine induces early growth response factor-1 expression and activates the core promoter of PDGF-A chain in vascular endothelial cells.	2001 May	11348873
p38 MAP kinase negatively regulates cyclin D1 expression in airway smooth muscle cells.	2001 May	11290520
Activation of Na+/H+ exchanger-directed protein kinases in the ischemic and ischemic-reperfused rat myocardium.	2001 May 11	11279085
TNF-alpha enhances intracellular glucocorticoid availability.	2001 Nov 2	11696370
Regulation and distribution of MAdCAM-1 in endothelial cells in vitro.	2001 Oct	11546645
Quercetin abrogates taxol-mediated signaling by inhibiting multiple kinases.	2001 Oct 15	11597122
Inhibition of the ERK pathway prevents HIVgp120-induced REM sleep increase.	2001 Sep 14	11532249
Transforming growth factor-beta1 causes transcriptional activation of CD34 and preserves haematopoietic stem/progenitor cell activity.	2002 Aug	12139758
Transforming growth factor-beta1 transcriptionally activates CD34 and prevents induced differentiation of TF-1 cells in the absence of any cell-cycle effects.	2002 Jan	11840268
Indomethacin causes prostaglandin D(2)-like and eotaxin-like selective responses in eosinophils and basophils.	2002 Jul 19	11980903
p38 Mitogen-activated protein kinase mediates hypoxic regulation of Mdm2 and p53 in neurons.	2002 Jun 21	11948180
CTLA-4-Ig regulates tryptophan catabolism in vivo.	2002 Nov	12368911
Potentiation of liver X receptor transcriptional activity by peroxisome-proliferator-activated receptor gamma co-activator 1 alpha.	2003 Apr 1	12470296
Evidence for a role of p38 kinase in hypoxia-inducible factor 1-independent induction of vascular endothelial growth factor expression by sodium arsenite.	2003 Feb 28	12482858
Bone morphogenetic protein signaling in articular chondrocyte differentiation.	2003 Feb 7	12565908

Patents

Sample Use Guides

In Vivo Use Guide

In a rat model for the study of renal ischemia SB-202190 was conjugated to lysozyme using a universal linkage system (SB-ULS-LZM) and delivered intravenously through the penile vein under inhalation anesthesia. The conjugate was dosed at 32 mg/kg which is the equivalent of 752 g/kg SB-202190 and dissolved in 5% glucose 2 hours before inducing ischemia. A reduction of reduction in p-p38-positive cells was demonstrated in both the cortex and medulla and reduced alpha-SMA expression (a biomarker for fibrosis).

Route of Administration: Intravenous

In Vitro Use Guide

T-lymphocyte Jurkat cells were serum-starved for 24 h and then treated with 50 uM of the specific p38 inhibitor SB-202190. The cell viability was monitored by trypan blue exclusion. The ability of SB-202190 to induce cell death was shown in a dose-dependent manner and achieving half the maximal death after 14 hours. The pattern of apoptosis included both nucleus condensation and DNA fragmentation. Results suggest that the effect of SB-202190 may be related to its inhibition on p38.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:11:07 UTC 2023` Edited by `admin` on `Fri Dec 15 18:11:07 UTC 2023`
Record UNII	PVX798P8GI
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SB-202190

Common Name

English

SB202190

Code

English

4-(4-FLUOROPHENYL)-2-(4-HYDROXYPHENYL)-5-(4-PYRIDYL)IMIDAZOLE

Systematic Name

English

PHENOL, 4-(4-(4-FLUOROPHENYL)-5-(4-PYRIDINYL)-1H-IMIDAZOL-2-YL)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID7041120