| Identification | Back Directory | [Name]
Necrostatin-5 | [CAS]
337349-54-9 | [Synonyms]
Necrostatin-5
Necrostatin-5 (Nec-5)
Necrostatin-5 >=98% (HPLC), solid
3-p-methoxyphenyl-5,6-tetramethylenothieno[2,3-d]pyrimidin-4-one-2-mercaptoethylcyanide
2-[[3,4,5,6,7,8-Hexahydro-3-(4-methoxyphenyl)-4-oxo[1]benzothieno[2,3-d]pyrimidin-2-yl]thio]-acetonitrile
Acetonitrile, 2-[[3,4,5,6,7,8-hexahydro-3-(4-methoxyphenyl)-4-oxo[1]benzothieno[2,3-d]pyrimidin-2-yl]thio]- | [Molecular Formula]
C19H17N3O2S2 | [MDL Number]
MFCD01448275 | [MOL File]
337349-54-9.mol | [Molecular Weight]
383.49 |
| Chemical Properties | Back Directory | [Melting point ]
212-214℃ | [storage temp. ]
2-8°C | [solubility ]
DMSO: >10mg/mL | [form ]
solid | [color ]
white to off-white | [InChI]
1S/C19H17N3O2S2/c1-24-13-8-6-12(7-9-13)22-18(23)16-14-4-2-3-5-15(14)26-17(16)21-19(22)25-11-10-20/h6-9H,2-5,11H2,1H3 | [InChIKey]
VGONMECBFMCKBS-UHFFFAOYSA-N | [SMILES]
COc1ccc(cc1)N2C(=O)c3c4CCCCc4sc3N=C2SCC#N |
| Hazard Information | Back Directory | [Uses]
Necrostatin-5 (Nec-5) is a potent necroptosis inhibitor with an EC50 value of 0.24 μM. Necrostatin-5 also is a RIP1 inhibitor. Necrostatin-5 shows cardioprotective effects[1][2][3]. | [Biological Activity]
Necrostatin-5 is an inhibitor of necroptosis (non-apoptotic cell death pathway) by indirect inhibition of RIP1 kinase. Necroptosis is defined as alternative active cell death pathway: Death-Domain Receptor (DRse.g. Fas/TNFR) mediated and caspase-inhibitor insensitive with specific morphology (nuclear condensationorganelle swellingloss of plasma membrane integrity). The necrostatins have been discovered to inhibit this pathway by inhibition of the death domain receptor-associated adaptor kinase RIP1. Three distinct mechanisms appear to be involved: T-loop dependent inhibition by necrostatin-1; partially T-loop independent inhibition by necrostatin-3 and indirect inhibition of RIP1 by necrostatin-5since necrostatin-5 is a potent inhibitor of immunnoprecipitated RIP1but does not inhibit recombinant RIP1. | [in vivo]
Necrostatin-5 (2.46 mg/kg; i.p.) shows cardioprotective effects on the isolated heart model in rats[2]. | Animal Model: | 200-300 g, male Wistar rats[2] | | Dosage: | 2.46 mg/kg | | Administration: | I.p.; 60 min before experiment | | Result: | Reduced the infarction zone caused by 30-min global ischemia and 120-min reperfusion. |
| [IC 50]
RIPK1; necroptosis: 0.24 μM (EC50) | [storage]
Store at -20°C | [References]
[1] Wang K, et al. Structure-activity relationship analysis of a novel necroptosis inhibitor, Necrostatin-5. Bioorg Med Chem Lett. 2007 Mar 1;17(5):1455-65. DOI:10.1016/j.bmcl.2006.11.056
[2] Dmitriev YV, et al. Study of cardioprotective effects of necroptosis inhibitors on isolated rat heart subjected to global ischemia-reperfusion. Bull Exp Biol Med. 2013 Jun;155(2):245-8. DOI:10.1007/s10517-013-2124-2
[3] González-Juarbe N, et al. Pore-Forming Toxins Induce Macrophage Necroptosis during Acute Bacterial Pneumonia. PLoS Pathog. 2015 Dec 11;11(12):e1005337. DOI:10.1371/journal.ppat.1005337 |
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Energy Chemical
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http://www.energy-chemical.com |
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