1,1,1,3,3,3-Hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

Synopsis, Chemistry

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1,1,1,3,3,3-Hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

Also known as: Abx-1431, 1446817-84-0, Abx1431, Fb39e94uxk, 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate, 1,1,1,3,3,3-hexafluoropropan-2-yl-4-[[2-(pyrrolidin-1-yl)-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

Molecular Formula

C₂₀H₂₂F₉N₃O₂

Molecular Weight

507.4 g/mol

InChI Key

SQZJGTOZFRNWCX-UHFFFAOYSA-N

FDA UNII

FB39E94UXK

Elcubragistat is an orally bioavailable inhibitor of the serine hydrolase monoacylglycerol lipase (MGLL), with potential use for the treatment of various central nervous system (CNS) diseases and with potential analgesic and anti-neuroinflammatory activities. Upon oral administration, elcubragistat targets and binds to MGLL, thereby inhibiting MGLL activity and preventing the breakdown and inactivation of endogenous 2-arachidonoylglycerol (2-AG). Increased 2-AG levels results in enhanced activation of the cannabinoid receptor 1 (CB1) in the CNS and enhanced CB1 endocannabinoid signaling in active neural circuits. Activation of CB1 helps modulate the endocannabinoid system and reduce neurotransmitter release, thereby decreasing overactive neural signaling. This induces analgesic, anti-inflammatory and various neurological effects that are caused by dysregulation of the endocannabinoid system and overactive neural signaling, including anxiolytic effects, reduced spasticity and decreased neurodegenerative effects. In addition, MGLL inhibition by elcubragistat depletes the supply of the inflammatory signaling molecule arachidonic acid, thereby further alleviating pain and inflammation. CB1 plays a key role in the regulation of neurotransmission; increased CB1 activation decreases overactive neural signaling. MGLL, an enzyme that catalyzes the breakdown of 2-AG, regulates the activation of CB1 and CB2 to modulate neurotransmission and inflammatory signaling, respectively.

1 2D Structure

1,1,1,3,3,3-Hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

2.1.2 InChI

InChI=1S/C20H22F9N3O2/c21-18(22,23)14-4-3-13(15(11-14)31-5-1-2-6-31)12-30-7-9-32(10-8-30)17(33)34-16(19(24,25)26)20(27,28)29/h3-4,11,16H,1-2,5-10,12H2

2.1.3 InChI Key

SQZJGTOZFRNWCX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CCN(C1)C2=C(C=CC(=C2)C(F)(F)F)CN3CCN(CC3)C(=O)OC(C(F)(F)F)C(F)(F)F

2.2 Other Identifiers

2.2.1 UNII

FB39E94UXK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,1,1,3,3,3-hexafluoro-2-propanyl 4-(2-(1-pyrrolidinyl)-4-(trifluoromethyl)benzyl)-1-piperazinecarboxylate

2. 1-piperazinecarboxylic Acid, 4-((2-(1-pyrrolidinyl)-4-(trifluoromethyl)phenyl)methyl)-, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl Ester

3. Abx-1431

2.3.2 Depositor-Supplied Synonyms

1. Abx-1431

2. 1446817-84-0

3. Abx1431

4. Fb39e94uxk

5. 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

6. 1,1,1,3,3,3-hexafluoropropan-2-yl-4-[[2-(pyrrolidin-1-yl)-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate

7. 1-piperazinecarboxylic Acid, 4-((2-(1-pyrrolidinyl)-4-(trifluoromethyl)phenyl)methyl)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl Ester

8. Elcubragistat

9. Unii-fb39e94uxk

10. Elcubragistat [inn]

11. Chembl3945728

12. Schembl15100632

13. Gtpl10062

14. Bdbm180052

15. Us9133148, 9aq

16. Abx 1431

17. Bcp29967

18. Ex-a2760

19. Abx1431;abx 1431

20. S8823

21. Akos037515667

22. Compound 28 [pmid: 30067909]

23. Compound 9aq [wo2013103973a1]

24. Ac-35611

25. Ba167497

26. Bs-15747

27. Example 82 [wo2013103973a1]

28. Hy-117632

29. Cs-0066666

30. 4-(trifluoromethyl)phenyl]methyl]piperazine-1-

31. D80627

32. 1,1,1,3,3,3-hexafluoropropan-2-yl-4-[[2-(pyrrolidin-1-yl)-

2.4 Create Date

2013-08-19

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₂F₉N₃O₂
Molecular Weight	507.4 g/mol
XLogP3	5.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	5
Exact Mass	507.15683041 g/mol
Monoisotopic Mass	507.15683041 g/mol
Topological Polar Surface Area	36 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	670
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1