JNJ-42165279   

GtoPdb Ligand ID: 9012

Synonyms: Example 1 [WO2011139951 A1] [3] | JNJ42165279
Compound class: Synthetic organic
Comment: JNJ-42165279 is an investigational, covalent and selective inhibitor of fatty acid amide hydrolase (FAAH) [3]. Preclinical test findings are reported in [2], with the conclusion that the favourable ADME and pharmacodynamic profiles of JNJ-42165279 supported it being progressed to clinical trial.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 66.93
Molecular weight 410.1
XLogP 1.98
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(N1CCN(CC1)Cc1ccc2c(c1)OC(O2)(F)F)Nc1cnccc1Cl
Isomeric SMILES O=C(N1CCN(CC1)Cc1ccc2c(c1)OC(O2)(F)F)Nc1cnccc1Cl
InChI InChI=1S/C18H17ClF2N4O3/c19-13-3-4-22-10-14(13)23-17(26)25-7-5-24(6-8-25)11-12-1-2-15-16(9-12)28-18(20,21)27-15/h1-4,9-10H,5-8,11H2,(H,23,26)
InChI Key YWGYNGCRVZLMCS-UHFFFAOYSA-N
References
1. Janero DR, Vadivel SK, Makriyannis A. (2009)
Pharmacotherapeutic modulation of the endocannabinoid signalling system in psychiatric disorders: drug-discovery strategies.
Int Rev Psychiatry, 21 (2): 122-33. [PMID:19367506]
2. Keith JM, Jones WM, Tichenor M, Liu J, Seierstad M, Palmer JA, Webb M, Karbarz M, Scott BP, Wilson SJ et al.. (2015)
Preclinical Characterization of the FAAH Inhibitor JNJ-42165279.
ACS Med Chem Lett, 6 (12): 1204-8. [PMID:26713105]
3. Keith JM, Liu J. (2011)
Modulators of fatty acid amide hydrolase.
Patent number: WO2011139951 A1. Assignee: Janssen Pharmaceutica Nv. Priority date: 03/05/2010. Publication date: 10/11/2011.
4. Pertwee RG. (2014)
Elevating endocannabinoid levels: pharmacological strategies and potential therapeutic applications.
Proc Nutr Soc, 73 (1): 96-105. [PMID:24135210]
5. Sałaga M, Sobczak M, Fichna J. (2014)
Inhibition of fatty acid amide hydrolase (FAAH) as a novel therapeutic strategy in the treatment of pain and inflammatory diseases in the gastrointestinal tract.
Eur J Pharm Sci, 52: 173-9. [PMID:24275607]