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Dapansutrile
Also known as: 54863-37-5, 3-methanesulfonylpropanenitrile, 3-(methylsulfonyl)propanenitrile, Olt1177, Olt-1177, Dapansutrile [inn]
Molecular Formula
C4H7NO2S
Molecular Weight
133.17  g/mol
InChI Key
LQFRYKBDZNPJSW-UHFFFAOYSA-N
FDA UNII
2Z03364G96

Dapansutrile is an orally bioavailable inhibitor of the innate immune signaling sensor nucleotide-binding domain and leucine-rich repeat (NLR) family pyrin domain containing 3 (NLRP3; NACHT, LRR and PYD containing protein 3; NALP3), with potential immunomodulatory and anti-inflammatory activities. 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.
1 2D Structure

Dapansutrile

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-methylsulfonylpropanenitrile
2.1.2 InChI
InChI=1S/C4H7NO2S/c1-8(6,7)4-2-3-5/h2,4H2,1H3
2.1.3 InChI Key
LQFRYKBDZNPJSW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CS(=O)(=O)CCC#N
2.2 Other Identifiers
2.2.1 UNII
2Z03364G96
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(methylsulfonyl)propanenitrile

2. Olt-1177

3. Olt117

4. Olt1177

2.3.2 Depositor-Supplied Synonyms

1. 54863-37-5

2. 3-methanesulfonylpropanenitrile

3. 3-(methylsulfonyl)propanenitrile

4. Olt1177

5. Olt-1177

6. Dapansutrile [inn]

7. 3-methylsulfonylpropionitrile

8. 3-methylsulfonylpropanenitrile

9. 3-(methanesulfonyl)propanenitrile

10. Propanenitrile, 3-(methylsulfonyl)-

11. 2z03364g96

12. Dapansutrile(olt1177)

13. Dapansutrile (usan/inn)

14. Dapansutrile [usan:inn]

15. Dapansutrile [usan]

16. Dapansutrile (olt1177)

17. Dapansutrile [who-dd]

18. 3-methylsulphonyl-propionitrile

19. Schembl9934796

20. Chembl3989943

21. Gtpl10056

22. Dtxsid601336541

23. Unii-2z03364g96

24. Ex-a4519

25. Bdbm50505850

26. S8907

27. Zinc32005410

28. Akos010140086

29. Ac-36465

30. Bs-45330

31. Hy-17629

32. Cs-0016785

33. D5955

34. D10920

35. E74469

36. A936206

37. Q27255815

38. Z2719319073

2.4 Create Date
2007-02-08
3 Chemical and Physical Properties
Molecular Weight 133.17 g/mol
Molecular Formula C4H7NO2S
XLogP3-0.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass133.01974964 g/mol
Monoisotopic Mass133.01974964 g/mol
Topological Polar Surface Area66.3 Ų
Heavy Atom Count8
Formal Charge0
Complexity190
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


4.2 Mechanism of Action

Dapansutrile specifically inhibits the NLRP3 inflammasome and subsequent activation of IL-1. It is currently being investigated against gout flares, joint pain and COVID-19.


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