SKF 86002

Names

[ Name ]:
SKF 86002

[Synonym ]:
5-(4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo(2,1-b)-thiazole
MFCD00869367
6-(4-Fluorophenyl)-5-(4-pyridinyl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole
6-(4-Fluorophenyl)-5-(pyridin-4-yl)-2,3-dihydroimidazo[2,1-b][1,3]thiazole
Imidazo[2,1-b]thiazole, 6-(4-fluorophenyl)-2,3-dihydro-5-(4-pyridinyl)-
SKF-86002

Biological Activity

[Description]:

SKF-86002 is a potent inhibitor of p38 MAP kinase wit IC50 of 0.5-1 uM; inhibits LPS-induced IL-1 and TNF-α production in human monocytes (IC50 = 1 μM).IC50 value:Target: p38 MAPK inhibitorin vitro: SKF-86002 inhibited prostaglandin H2 (PGH2) synthase activity (IC50 120 microM) as well as prostanoid production by rat basophilic leukemia (RBL-1) cells (IC50 70 microM) and its sonicate (IC50 100 microM) and human monocytes (IC50 1 microM). In addition, SK&F 86002 inhibited the generation of dihydroxyeicosatetraenoic acid (diHETE) and 5-hydroxyeicosatetraenoic acid (5-HETE) by a high speed supernatant fraction of RBL-1 cells (IC50 10 microM) [1]. differentiation of HL-60 cells toward the neutrophil phenotype resulted in a loss in c-Jun NH2-terminal kinase activation with concomitant acquisition of formylmethionylleucylphenylalanine-stimulatable and stress-inducible p38 MAPK activity as well as apoptosis blockade by SKF-86002 [2]. SKF-86002 blocked superoxide anion production in response to FMLP and reduced adhesion and chemotaxis in response to PAF or FMLP [3].

[Related Catalog]:

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Inflammation/Immunology

[References]

[1]. Griswold DE, et al. SK&F 86002: a structurally novel anti-inflammatory agent that inhibits lipoxygenase- and cyclooxygenase-mediated metabolism of arachidonic acid. Biochem Pharmacol. 1987 Oct 15;36(20):3463-70.

[2]. Frasch SC, et al. p38 mitogen-activated protein kinase-dependent and -independent intracellular signal transduction pathways leading to apoptosis in human neutrophils. J Biol Chem. 1998 Apr 3;273(14):8389-97.

[3]. Nick JA, et al. Common and distinct intracellular signaling pathways in human neutrophils utilized by platelet activating factor and FMLP. J Clin Invest. 1997 Mar 1;99(5):975-86.

[Related Small Molecules]

SB203580 | SB202190 (FHPI) | Doramapimod (BIRB 796) | LY2228820 | SB 239063 | Losmapimod | PD 169316 | Talmapimod | Tat-NR2B9c | Dehydrocorydaline chloride | TAK-715 | VX 702 | VX-745 | Acumapimod | PH-797804

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
476.1±55.0 °C at 760 mmHg

[ Melting Point ]:
189-190ºC(lit.)

[ Molecular Formula ]:
C₁₆H₁₂FN₃S

[ Molecular Weight ]:
297.350

[ Flash Point ]:
241.7±31.5 °C

[ Exact Mass ]:
297.073608

[ PSA ]:
56.01000

[ LogP ]:
1.90

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.713

[ Storage condition ]:
2-8℃

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934100090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934100090

[ Summary ]:
2934100090 other compounds containing an unfused thiazole ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

Articles

The discovery of novel chemotypes of p38 kinase inhibitors.

Curr. Top. Med. Chem 5(10) , 953-65, (2005)

In the late 1970s and the early 1980s the initial p38 chemotype, the triaryl imidazoles, was discovered as an off-target effect during the development of cyclooxygenase and 5-lipoxygenase inhibitors l...

Activation of p38MAPK contributes to expanded polyglutamine-induced cytotoxicity.

PLoS ONE 3(5) , e2130, (2008)

The signaling pathways that may modulate the pathogenesis of diseases induced by expanded polyglutamine proteins are not well understood.Herein we demonstrate that expanded polyglutamine protein cytot...

Differential activation of the c-Jun N-terminal kinase pathway in arsenite-induced apoptosis and sensitization of chemically resistant compared to susceptible B-lymphoma cell lines.

Toxicol. Sci. 68(1) , 82-92, (2002)

Various forms of inorganic arsenic are significant environmental contaminants that have multiple effects on cells, including the induction of apoptotic cell death. Induction of apoptosis in lymphoid c...