| Identification | Back Directory | [Name]
SB 220025 | [CAS]
165806-53-1 | [Synonyms]
SB 220025
5-(2-AMINO-4-PYRIMIDINYL)-4-(4-FLUOROPHENYL)-1-(4-PIPERIDINYL)IMIDAZOLE
5-(2-AMINO-4-PYRIMIDINYL)-4-(4-FLUOROPHENYL)-1-(4-PIPERIDINLYL)IMIDAZOLE
4-[4-(4-fluorophenyl)-1-(piperidin-4-yl)-1H-imidazol-5-yl]pyrimidin-2-amine
2-Pyrimidinamine, 4-[4-(4-fluorophenyl)-1-(4-piperidinyl)-1H-imidazol-5-yl]- | [Molecular Formula]
C18H19FN6 | [MDL Number]
MFCD02179213 | [MOL File]
165806-53-1.mol | [Molecular Weight]
338.38 |
| Chemical Properties | Back Directory | [Boiling point ]
611.9±65.0 °C(Predicted) | [density ]
1.42±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: 22mg/mL | [form ]
White to pale amber solid. | [pka]
9.92±0.10(Predicted) | [color ]
white to pale yellow | [InChI]
1S/C18H19FN6/c19-13-3-1-12(2-4-13)16-17(15-7-10-22-18(20)24-15)25(11-23-16)14-5-8-21-9-6-14/h1-4,7,10-11,14,21H,5-6,8-9H2,(H2,20,22,24) | [InChIKey]
VSPFURGQAYMVAN-UHFFFAOYSA-N | [SMILES]
Fc1ccc(cc1)c2nc[n](c2c4nc(ncc4)N)C3CCNCC3 |
| Hazard Information | Back Directory | [Uses]
SB 220025 is a reversible, orally active, cell-permeable, ATP-competitive and selective human p38 MAPK inhibitor (IC50 = 60 nM). SB 220025 also inhibits p56Lck and PKC with IC50 values of 3.5 and 2.89 μM, respectively. SB 220025 inhibits the expression of IL-8 gene in response to globular adiponectin (gAd), reduces inflammatory cytokine production and inhibits angiogenesis. SB 220025 effectively prevents the progression of arthritis in a chronic inflammatory disease model and can be used in the study of inflammation[1][2]. | [Definition]
ChEBI: SB220025 is am member of the class of imidazoles carrying piperidin-4-yl, 4-fluophenyl and 2-aminopyrimidin-4-yl substituents at posiitons 1, 4 and 5 respectively. It has a role as an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor, an angiogenesis inhibitor and an anti-inflammatory agent. It is a member of piperidines, an organofluorine compound, an aminopyrimidine and a member of imidazoles. | [Biological Activity]
Primary Target
P38MAPK | [in vivo]
SB 220025 (3-50 mg/kg; p.o.; single) inhibits inflammatory cytokine production in vivo[2].
SB 220025 (5, 30, 50 mg/kg; i.p.; b.i.d.) inhibits angiogenesis in the murine air pouch granuloma model[2].
SB 220025 (30 mg/kg; p.o.; twice a day for 3, 5, 7 or 14 days) prevents the increase in angiogenesis that occurs after day 3 in murine air pouch angiogenesis model[2].
SB 220025 (50 mg/kg; p.o.; b.i.d.; 10 days) effectively blocks the progression of arthritis in a chronic inflammatory disease model[2]. | Animal Model: | Acute model of LPS-induced TNF-a expression[2]. | | Dosage: | 3-50 mg/kg | | Administration: | Oral administration; single; 30 min before challenge with LPS. | | Result: | Dosedependently inhibited TNF-a production with an ED50 value of 7.5 mg/kg, and showed more than 80% inhibition when at 50 mg/kg. |
| Animal Model: | Murine air pouch granuloma model[2]. | | Dosage: | 5, 30, 50 mg/kg | | Administration: | Intraperitoneal injection; bisindie (bid, twice a day). | | Result: | Caused a dose-dependent reduction in angiogenesis. |
| Animal Model: | Murine air pouch granuloma model[2]. | | Dosage: | 30 mg/kg | | Administration: | Oral administration; twice a day from day 0 until removal of granuloma tissue at days 3, 5, 7 or 14. | | Result: | Did not affect the initial burst of angiogenesis but did prevent the increase in angiogenesis that occurs after day 3. |
| [IC 50]
p38: 60 nM (IC50); p56-Lck: 3.5 μM (IC50); PKC: 2.89 μM (IC50) | [References]
[1] Tomizawa A, et al. Induction of gene expression in response to globular adiponectin in vascular endothelial cells. Life Sci. 2009 Sep 9;85(11-12):457-61. DOI:10.1016/j.lfs.2009.07.012
[2] Jackson JR, et al. Pharmacological effects of SB 220025, a selective inhibitor of P38 mitogen-activated protein kinase, in angiogenesis and chronic inflammatory disease models. J Pharmacol Exp Ther. 1998 Feb;284(2):687-92. PMID:9454815 |
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| Company Name: |
Merck Millipore
|
| Tel: |
1-400-889-1988 400-889-1988 |
| Website: |
http://www.merckmillipore.com |
| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
|