| Identification | More | [Name]
1,9-Pyrazoloanthrone | [CAS]
129-56-6 | [Synonyms]
1 9-PYRAZOLEANTHRONE
1,9-PYRAZOLOANTHRONE
2H-DIBENZO[CD,G]INDAZOL-6-ONE
ANTHRA(1,9-CD)PYRAZOL-6(2H)-ONE
ANTHRA-1,9-PYRAZOL-6-NONE
ANTHRAPYRAZOLONE
JNK INHIBITOR II
SAPK INHIBITOR I
SAPK INHIBITOR II
SP600125
TIMTEC-BB SBB000595
c.i.70300
pyrazolanthrone
3H-naphtho[2,3-f]indazol-3-one
1,9-Pyrazoloanthrone, Anthrapyrazolone
JNKII | [EINECS(EC#)]
204-955-6 | [Molecular Formula]
C14H8N2O | [MDL Number]
MFCD00022289 | [Molecular Weight]
220.23 | [MOL File]
129-56-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
281~282℃ | [Boiling point ]
361.16°C (rough estimate) | [density ]
1.1702 (rough estimate) | [refractive index ]
1.5910 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
H2O: insoluble
| [form ]
Yellowish orange solid | [pka]
11.75±0.20(Predicted) | [color ]
yellow
| [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months | [InChIKey]
ACPOUJIDANTYHO-UHFFFAOYSA-N | [CAS DataBase Reference]
129-56-6(CAS DataBase Reference) | [EPA Substance Registry System]
129-56-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
CB4585000
| [TSCA ]
Yes | [HS Code ]
29339900 | [Toxicity]
LD50 ivn-mus: 178 mg/kg CSLNX* NX#00640 |
| Hazard Information | Back Directory | [Description]
SP-600125 (129-56-6) is a selective inhibitor of c-Jun N-terminal kinase (JNK). Reversibly inhibits JNK1,2 and 3 (IC50‘s range from 40-90 nM). >300-fold selectivity for JNK as compared to related MAP kinases. Anti-inflammatory activity. SP-600125 inhibits expression of presenilin-1 and Notch signaling in mouse brain. Cell permeable and active in vivo. | [Uses]
A broad-spectrum serine/threonine kinase inhibitor of JNK with an IC50 range from 40 to 90 nM. | [Definition]
ChEBI: A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase. | [General Description]
A potent, cell-permeable, selective, and reversible inhibitor of c-Jun N-terminal kinase (JNK) (IC50 = 40 nM for JNK-1 and JNK-2 and 90 nM for JNK-3). The inhibition is competitive with respect to ATP. Exhibits over 300-fold greater selectivity for JNK as compared to ERK1 and p38-2 MAP kinases. Inhibits the phosphorylation of c-Jun and blocks the expression of IL-2, IFN-γ, TNF-α, and COX-2 in cells. Blocks IL-1-induced accumulation of phospho-Jun and induction of c-Jun transcription. | [Biological Activity]
Selective inhibitor of c-Jun N-terminal kinase (JNK). Competitively and reversibly inhibits JNK1, 2 and 3 (IC 50 = 40-90 nM) with negligible activity at ERK2, p38 β and a range of enzymes (IC 50 > 10 μ M). Active in vivo . Shown to have reduced selectivity over other protein kinases under certain conditions. Protects renal tubular epithelial cells against ischemia/reperfusion-induced apoptosis. Also available as part of the MAPK Inhibitor Tocriset™ . | [Biochem/physiol Actions]
SP600125 is an anthrapyrazolone inhibitor of JNK that competes with ATP to inhibit the phosphorylation of c-Jun. It prevents the activation of inflammatory genes such as COX-2, IL-2 IFN-γ and TNF-α.8,9 It prevents the activation of JNK after brain ischemia and may be effective in treatment of ischemic stroke.10 | [Safety Profile]
Poison by intravenous route.When heated to decomposition it emits toxic fumes ofNOx. | [Synthesis]
1,9-Pyrazolanthrone is prepared by diazotization
of 1-aminoanthraquinone, reaction of the
diazonium salt with sodium hydrogen sulfite,
and cyclization of the resulting hydrazinosulfonic
acid . | [storage]
-20°C (desiccate) | [References]
1)Bennett et al. (2001), SP600125, an anthrapyrazolone inhibitor of Jun N-terminal kinase; Proc. Natl. Acad. Sci. USA., 98 13681
2) Rahman et al. (2012), Intraperitoneal injection of JNK-specific inhibitor SP600125 inhibits the expression of presenilin-1 and Notch signaling in mouse brain without induction of apoptosis; Brain Res., 1448 117 |
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