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 8504		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 8504		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 609 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
Tumor promoter arsenite stimulates histone H3 phosphoacetylation of proto-oncogenes c-fos and c-jun chromatin in human diploid fibroblasts.	2003-04-11	12547826
Potentiation of liver X receptor transcriptional activity by peroxisome-proliferator-activated receptor gamma co-activator 1 alpha.	2003-04-01	12470296
Evidence for a role of p38 kinase in hypoxia-inducible factor 1-independent induction of vascular endothelial growth factor expression by sodium arsenite.	2003-02-28	12482858
Bone morphogenetic protein signaling in articular chondrocyte differentiation.	2003-02-07	12565908
Effects of inhibition of myocardial extracellular-responsive kinase and P38 mitogen-activated protein kinase on mechanical function of rat hearts after prolonged hypothermic ischemia.	2003-01-27	12548118
Peroxisome proliferator-activated receptor-beta signaling contributes to enhanced proliferation of hepatic stellate cells.	2003-01	12512042
Inhibition of p38 mitogen-activated protein kinase blocks activation of rat pancreatic stellate cells.	2003-01	12490569
A novel regulatory mechanism of the mitochondrial Ca2+ uniporter revealed by the p38 mitogen-activated protein kinase inhibitor SB202190.	2002-12	12368236
p38 Signaling-mediated hypoxia-inducible factor 1alpha and vascular endothelial growth factor induction by Cr(VI) in DU145 human prostate carcinoma cells.	2002-11-22	12213806
In vivo role of p38 mitogen-activated protein kinase in mediating the anti-inflammatory effects of CpG oligodeoxynucleotide in murine asthma.	2002-11-15	12421981
P38 mitogen-activated protein kinase inhibitor SB203580 has a bi-directional effect on iNOS expression and NO production.	2002-11-15	12421638
HIV-1 gp120-induced tubular epithelial cell apoptosis is mediated through p38-MAPK phosphorylation.	2002-11	12520084
Role of bioavailable iron in coal dust-induced activation of activator protein-1 and nuclear factor of activated T cells: difference between Pennsylvania and Utah coal dusts.	2002-11	12397016
CTLA-4-Ig regulates tryptophan catabolism in vivo.	2002-11	12368911
Large scale gene expression analysis of osteoclastogenesis in vitro and elucidation of NFAT2 as a key regulator.	2002-10-25	12171919
The role of p38 in UVA-induced cyclooxygenase-2 expression in the human keratinocyte cell line, HaCaT.	2002-10-10	12370831
Essential role of p38 mitogen-activated protein kinase in contact hypersensitivity.	2002-10-04	12138127
Macrophage apoptosis by anthrax lethal factor through p38 MAP kinase inhibition.	2002-09-20	12202685
Activation of mitogen-activated protein kinases (MAPKs) by aromatic hydrocarbons: role in the regulation of aryl hydrocarbon receptor (AHR) function.	2002-09	12213569
Caspase inhibitors induce a switch from apoptotic to proinflammatory signaling in CD95-stimulated T lymphocytes.	2002-09	12207331
The role of mitogen-activated protein kinases in eotaxin-induced cytokine production from bronchial epithelial cells.	2002-09	12204895
Enhancement of oxidative stress-induced apoptosis by Hsp105alpha in mouse embryonal F9 cells.	2002-08	12180991
Transforming growth factor-beta1 causes transcriptional activation of CD34 and preserves haematopoietic stem/progenitor cell activity.	2002-08	12139758
Indomethacin causes prostaglandin D(2)-like and eotaxin-like selective responses in eosinophils and basophils.	2002-07-19	11980903
Activation of JNK1, RSK2, and MSK1 is involved in serine 112 phosphorylation of Bad by ultraviolet B radiation.	2002-07-05	11983683
Activation and translocation of p38 mitogen-activated protein kinase after stimulation of monocytes with contact sensitizers.	2002-07	12164931
The roles of ERK1/2 and p38 MAP kinases in the preventive mechanisms of mushroom Phellinus linteus against the inhibition of gap junctional intercellular communication by hydrogen peroxide.	2002-07	12117774
The role of p38 map kinase in tumor necrosis factor-induced redistribution of vascular endothelial cadherin and increased endothelial permeability.	2002-07	12095140
Sustained exposure of L6 myotubes to high glucose and insulin decreases insulin-stimulated GLUT4 translocation but upregulates GLUT4 activity.	2002-07	12086937
Pyridinylimidazole p38 mitogen-activated protein kinase inhibitors block intracellular Toxoplasma gondii replication.	2002-07	12076626
p38 Mitogen-activated protein kinase mediates hypoxic regulation of Mdm2 and p53 in neurons.	2002-06-21	11948180
Irofulven (6-hydroxymethylacylfulvene, MGI 114)-induced apoptosis in human pancreatic cancer cells is mediated by ERK and JNK kinases.	2002-05-17	12014623
Peroxisome proliferator-activated receptor (PPAR) gamma coactivator-1 recruitment regulates PPAR subtype specificity.	2002-05-10	11875072
Intracellular calcium mobilization induces period genes via MAP kinase pathways in NIH3T3 cells.	2002-04-10	11959112
Pathways of induction of peroxiredoxin I expression in osteoblasts: roles of p38 mitogen-activated protein kinase and protein kinase C.	2002-04-05	11796722
A proteasome inhibitor confers cardioprotection.	2002-04	12062370
The oxidized lipid and lipoxygenase product 12(S)-hydroxyeicosatetraenoic acid induces hypertrophy and fibronectin transcription in vascular smooth muscle cells via p38 MAPK and cAMP response element-binding protein activation. Mediation of angiotensin II effects.	2002-03-22	11786549
Phosphorylation of 4E-BP1 is mediated by the p38/MSK1 pathway in response to UVB irradiation.	2002-03-15	11777913
Glucocorticoids induced the production and gene expression of IL-1alpha through AP-1 and partially NF-kappaB activation in murine epidermal cells.	2002-03	12160224
ERK and p38 MAP kinase are involved in arachidonic acid release induced by H(2)O(2) and PDGF in mesangial cells.	2002-03	11832430
IL-4 up-regulates the expression of tissue inhibitor of metalloproteinase-2 in dermal fibroblasts via the p38 mitogen-activated protein kinase dependent pathway.	2002-02-15	11823524
Distinct role of p38 and c-Jun N-terminal kinases in IL-10-dependent and IL-10-independent regulation of the costimulatory molecule B7.2 in lipopolysaccharide-stimulated human monocytic cells.	2002-02-15	11823508
Transforming growth factor-beta1 transcriptionally activates CD34 and prevents induced differentiation of TF-1 cells in the absence of any cell-cycle effects.	2002-01	11840268
The phosphatidylinositol 3-kinase, p38, and extracellular signal-regulated kinase pathways are involved in osteoclast differentiation.	2002-01	11792567
Activation of p38 mitogen-activated protein kinase during normal mitosis in the developing retina.	2002	12074900
Proliferative and morphological effects of endothelins in Schwann cells: roles of p38 mitogen-activated protein kinase and Ca(2+)-independent phospholipase A2.	2001-12	11752055
TNF-alpha and interleukin 1 activate gastrin gene expression via MAPK- and PKC-dependent mechanisms.	2001-12	11705745
Differential regulation of diverse physiological responses to VEGF in pulmonary endothelial cells.	2001-12	11704547
Possible involvement of p38 mitogen-activated protein kinase in decidual function in parturition.	2001-11-16	11700032
The MKK6/p38 mitogen-activated protein kinase pathway is capable of inducing SOCS3 gene expression and inhibits IL-6-induced transcription.	2001-10	11727828

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 `Mon Mar 31 19:07:08 GMT 2025` Edited by `admin` on `Mon Mar 31 19:07:08 GMT 2025`
Record UNII	PVX798P8GI
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SB-202190

Common Name

English

SB202190

Preferred Name

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