Dapansutrile

Product NameDapansutrile
CAS54863-37-5
MFC4H7NO2S
MW133.17
EINECS
MOL File54863-37-5.mol

Chemical Properties

Melting point	71-72 °C(Solv: ethanol (64-17-5))
Boiling point	374.7±25.0 °C(Predicted)
Density	1+-.0.06 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO:60.0(Max Conc. mg/mL);450.55(Max Conc. mM) H2O:68.0(Max Conc. mg/mL);510.63(Max Conc. mM)
form	A crystalline solid
color	White to off-white
InChI	InChI=1S/C4H7NO2S/c1-8(6,7)4-2-3-5/h2,4H2,1H3
InChIKey	LQFRYKBDZNPJSW-UHFFFAOYSA-N
SMILES	C(#N)CCS(C)(=O)=O

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Dapansutrile is an orally active β-sulfonyl nitrile compound that selectively inhibits the NLRP3 inflammasome.Upon oral administration, dapansutrile specifically binds to and inhibits NLRP3, the sensor component of the NLRP3 inflammasome, and prevents the formation of the NLRP3 inflammasome. This inhibits the production of the pro-inflammatory cytokines interleukin-1-beta (IL-1beta) and interleukin-18 (IL-18), which may prevent or reduce inflammation. NLRP3 plays an important role in immunity and inflammation.

Uses

Dapansutrile is used as NLRP3 inflammasome inhibitors, and is used to treat multiple sclerosis.

Biological Activity

Dapansutrile is a NLRP3 inflammasome inhibitor that disrupts inflammasome formation. Reduces LPS/ATP-induced IL-1β secretion in human and mouse macrophages in vitro, without affecting TNFα levels. Reduces LPS-induced inflammation in vivo. Also reduces joint swelling and markers of inflammation in synovial fluid in a mouse model of acute arthritis. Displays cardioprotective effects in a mouse model of cardiac ischemic reperfusion injury.

Side effects

Dapansutrile will be delivered as capsules for oral intake.
Side effects of dapansutrile may be: diarrhea, joint pain, headache.
There is a risk of an allergic reaction with the following symptoms: rash, difficulty breathing, wheezing, sudden drop in blood pressure, swelling around the mouth, throat or eyes, high pulse, sweating.

storage

Store at -20°C

References

[1] JUN-FENG CAO. Exploring the mechanism of action of dapansutrile in the treatment of gouty arthritis based on molecular docking and molecular dynamics.[J]. Frontiers in Physiology, 2022: 990469. DOI:10.3389/fphys.2022.990469.
[2] L TANG. Dapansutrile ameliorated chondrocyte inflammation and osteoarthritis through suppression of MAPK signaling pathway.[J]. Human & Experimental Toxicology, 2022, 41: 9603271221145401. DOI:10.1177/09603271221145401.
[3] XIAOSHENG WU. Secreted ORF8 induces monocytic pro-inflammatory cytokines through NLRP3 pathways in patients with severe COVID-19.[J]. iScience, 2023, 26 6: 106929. DOI:10.1016/j.isci.2023.106929.
[4] VIOLA KLüCK MD . Dapansutrile, an oral selective NLRP3 inflammasome inhibitor, for treatment of gout flares: an open-label, dose-adaptive, proof-of-concept, phase 2a trial[J]. Lancet Rheumatology, 2020, 2 5: Pages e270-e280. DOI:10.1016/S2665-9913(20)30065-5.

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