NLRP3-IN-2

Names

[ Name ]:
NLRP3-IN-2

[Synonym ]:
5-chloro-2-methoxy-N-[2-(4-sulphamoylphenyl)ethyl]benzamide
Benzamide, N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-chloro-2-methoxy-
5-Chloro-2-methoxy-N-[2-(4-sulfamoylphenyl)ethyl]benzamide
4-[2-(5-chloro-2-methoxy-benzamide)ethyl]-benzenesulphonamide
EINECS 240-722-5
5-Chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide
MFCD00193756

Biological Activity

[Description]:

NLRP3-IN-2, an intermediate substrate in the synthesis of glyburide, inhibits the formation of the NLRP3 inflammasome in cardiomyocytes and limits the infarct size following myocardial ischemia/reperfusion in the mouse, without affecting glucose metabolism[1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Immunology/Inflammation >> NOD-like Receptor (NLR)

[In Vivo]

NLRP3-IN-2 is well tolerated with no effects on the glucose levels in vivo[1]. NLRP3-IN-2 (100 mg/kg) treatment in a model of AMI due to ischemia+reperfusion significantly inhibits the activity of inflammasome (caspase-1) in the heart by 90% (P<0.01) and reduced infarct size, measured at pathology (by >40%, P<0.01) and with troponin I levels (by >70%, P<0.01) [1]. Animal Model: Experimental acute myocardial infarction (AMI) model in mice[1]. Dosage: 100 mg/kg. Administration: Intraperitoneal administration 30 minutes prior to surgery, then every 6 hours for 3 additional doses. Result: Led to a significant >90% reduction in caspase-1 activity (reflective of the formation of an active inflammasome) in the heart tissue measured 24 hours after ischemia. Led to a significant reduction in the infarct size measured with TTC (>40% reduction) or troponin I levels (>70% reduction) when compared with vehicle alone.

[References]

[1]. Carlo Marchetti, et al. A novel pharmacologic inhibitor of the NLRP3 inflammasome limits myocardial injury after ischemia-reperfusion in the mouse. J Cardiovasc Pharmacol. 2014 Apr;63(4):316-322.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
209-214 °C

[ Molecular Formula ]:
C₁₆H₁₇ClN₂O₄S

[ Molecular Weight ]:
368.835

[ Exact Mass ]:
368.059753

[ PSA ]:
106.87000

[ LogP ]:
1.74

[ Index of Refraction ]:
1.598

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
T

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S26-S36-S36/37-S22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2935009090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2935009090

[ Summary ]:
2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles

A novel pharmacologic inhibitor of the NLRP3 inflammasome limits myocardial injury after ischemia-reperfusion in the mouse.

J. Cardiovasc. Pharmacol. 63(4) , 316-22, (2014)

The formation of the NLRP3 inflammasome in the heart during acute myocardial infarction amplifies the inflammatory response and mediates further damage. Glyburide has NLRP3 inhibitory activity in vitr...

Trendelenburg G.

J. Cereb. Blood Flow Metab. , (2014)

Reply to Letter Regarding Article," NLRP3 Inflammasome as a Therapeutic Target in Myocardial Infarction. Takahashi M.

Int. Heart J. 55(4) , 380, (2014)