BMS-986142   

GtoPdb Ligand ID: 9857

Synonyms: BMS986142 | compound 14f [PMID: 27583770]
Compound class: Synthetic organic
Comment: BMS-986142 is a potent, highly selective and reversible small molecule BTK inhibitor [2-3], that is being investigated for anti-inflammatory potential [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 122.59
Molecular weight 572.22
XLogP 6.77
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Fc1cc(C(=O)N)c2c(c1c1cccc(c1C)n1c(=O)c3cccc(c3n(c1=O)C)F)c1CCC(Cc1[nH]2)C(O)(C)C
Isomeric SMILES Fc1cc(C(=O)N)c2c(c1c1cccc(c1C)n1c(=O)c3cccc(c3n(c1=O)C)F)c1CC[C@@H](Cc1[nH]2)C(O)(C)C
InChI InChI=1S/C32H30F2N4O4/c1-15-17(7-6-10-24(15)38-30(40)19-8-5-9-21(33)28(19)37(4)31(38)41)25-22(34)14-20(29(35)39)27-26(25)18-12-11-16(32(2,3)42)13-23(18)36-27/h5-10,14,16,36,42H,11-13H2,1-4H3,(H2,35,39)/t16-/m0/s1
InChI Key ZRYMMWAJAFUANM-INIZCTEOSA-N
References
1. Gillooly KM, Pulicicchio C, Pattoli MA, Cheng L, Skala S, Heimrich EM, McIntyre KW, Taylor TL, Kukral DW, Dudhgaonkar S et al.. (2017)
Bruton's tyrosine kinase inhibitor BMS-986142 in experimental models of rheumatoid arthritis enhances efficacy of agents representing clinical standard-of-care.
PLoS ONE, 12 (7): e0181782. [PMID:28742141]
2. Lee SK, Xing J, Catlett IM, Adamczyk R, Griffies A, Liu A, Murthy B, Nowak M. (2017)
Safety, pharmacokinetics, and pharmacodynamics of BMS-986142, a novel reversible BTK inhibitor, in healthy participants.
Eur. J. Clin. Pharmacol., 73 (6): 689-698. [PMID:28265691]
3. Watterson SH, De Lucca GV, Shi Q, Langevine CM, Liu Q, Batt DG, Beaudoin Bertrand M, Gong H, Dai J, Yip S et al.. (2016)
Discovery of 6-Fluoro-5-(R)-(3-(S)-(8-fluoro-1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)-2-methylphenyl)-2-(S)-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (BMS-986142): A Reversible Inhibitor of Bruton's Tyrosine Kinase (BTK) Conformationally Constrained by Two Locked Atropisomers.
J. Med. Chem., 59 (19): 9173-9200. [PMID:27583770]