suvorexant   Click here for help

GtoPdb Ligand ID: 2890

Synonyms: Belsomra® | DORA-analogue | MK 4305 | MK-4305
Approved drug PDB Ligand
suvorexant is an approved drug (FDA (2014))
Compound class: Synthetic organic
Comment: Suvorexant is the first approved orexin receptor antagonist drug. It is non-selective, being an equipotent antagonist of OX1 and OX2. The acronym for dual orexin receptor antagonist compounds/drugs is DORA.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 79.77
Molecular weight 450.16
XLogP 5.56
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Cc1ccc(c(c1)C(=O)N1CCN(CCC1C)c1oc2c(n1)cc(cc2)Cl)n1nccn1
Isomeric SMILES Cc1ccc(c(c1)C(=O)N1CCN(CC[C@H]1C)c1oc2c(n1)cc(cc2)Cl)n1nccn1
InChI InChI=1S/C23H23ClN6O2/c1-15-3-5-20(30-25-8-9-26-30)18(13-15)22(31)29-12-11-28(10-7-16(29)2)23-27-19-14-17(24)4-6-21(19)32-23/h3-6,8-9,13-14,16H,7,10-12H2,1-2H3/t16-/m1/s1
InChI Key JYTNQNCOQXFQPK-MRXNPFEDSA-N
References
1. Callander GE, Olorunda M, Monna D, Schuepbach E, Langenegger D, Betschart C, Hintermann S, Behnke D, Cotesta S, Fendt M et al.. (2013)
Kinetic properties of "dual" orexin receptor antagonists at OX1R and OX2R orexin receptors.
Front Neurosci, 7: 230. [PMID:24376396]
2. Cox CD, Breslin MJ, Whitman DB, Schreier JD, McGaughey GB, Bogusky MJ, Roecker AJ, Mercer SP, Bednar RA, Lemaire W, Bruno JG, Reiss DR, Harrell CM, Murphy KL, Garson SL, Doran SM, Prueksaritanont T, Anderson WB, Tang C, Roller S, Cabalu TD, Cui D, Hartman GD, Young SD, Koblan KS, Winrow CJ, Renger JJ, Coleman PJ. (2010)
Discovery of the dual orexin receptor antagonist [(7R)-4-(5-chloro-1,3-benzoxazol-2-yl)-7-methyl-1,4-diazepan-1-yl][5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (MK-4305) for the treatment of insomnia.
J Med Chem, 53 (14): 5320-32. [PMID:20565075]
3. de Lecea L and Sutcliffe JG. (2013)
Hypocretins (Orexins).  In  Handbook of Biologically Active Peptides 2nd edition
Edited by Kastin A (Academic Press) 812. [ISBN:9780123850966]
4. Li J, Hu Z, de Lecea L. (2014)
The hypocretins/orexins: integrators of multiple physiological functions.
Br J Pharmacol, 171 (2): 332-50. [PMID:24102345]
5. Mould R, Brown J, Marshall FH, Langmead CJ. (2014)
Binding kinetics differentiates functional antagonism of orexin-2 receptor ligands.
Br J Pharmacol, 171 (2): 351-63. [PMID:23692283]
6. Winrow CJ, Gotter AL, Cox CD, Doran SM, Tannenbaum PL, Breslin MJ, Garson SL, Fox SV, Harrell CM, Stevens J et al.. (2011)
Promotion of sleep by suvorexant-a novel dual orexin receptor antagonist.
J Neurogenet, 25 (1-2): 52-61. [PMID:21473737]