firazorexton   Click here for help

GtoPdb Ligand ID: 12603

Synonyms: TAK-994 (firazorexton sesquihydrate)
Compound class: Synthetic organic
Comment: Firazorexton (TAK-994) is a selective OX2 orexin receptor agonist (700-fold selectivity) [2]. Note that TAK-994 refers to a sesquihydrate formulation of firazorexton.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 95.09
Molecular weight 470.51
XLogP 0.63
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(C)(C(=O)N1CC[C@@H]([C@@H]1CC2=CC=CC(=C2F)C3=CC(=CC(=C3)F)F)NS(=O)(=O)C)O
Isomeric SMILES CC(C)(C(=O)N1CC[C@@H]([C@@H]1CC2=C(C(=CC=C2)C3=CC(=CC(=C3)F)F)F)NS(=O)(=O)C)O
InChI InChI=1S/C22H25F3N2O4S/c1-22(2,29)21(28)27-8-7-18(26-32(3,30)31)19(27)11-13-5-4-6-17(20(13)25)14-9-15(23)12-16(24)10-14/h4-6,9-10,12,18-19,26,29H,7-8,11H2,1-3H3/t18-,19-/m0/s1
InChI Key VOSAWOSMGPKQEQ-OALUTQOASA-N
References
1. Dauvilliers Y, Mignot E, Del Río Villegas R, Du Y, Hanson E, Inoue Y, Kadali H, Koundourakis E, Meyer S, Rogers R et al.. (2023)
Oral Orexin Receptor 2 Agonist in Narcolepsy Type 1.
N Engl J Med, 389 (4): 309-321. [PMID:37494485]
2. Ishikawa T, Hara H, Kawano A, Tohyama K, Kajita Y, Miyanohana Y, Koike T, Kimura H. (2023)
TAK-994, a Novel Orally Available Brain-Penetrant Orexin 2 Receptor-Selective Agonist, Suppresses Fragmentation of Wakefulness and Cataplexy-Like Episodes in Mouse Models of Narcolepsy.
J Pharmacol Exp Ther, 385 (3): 193-204. [PMID:37001988]
3. n/a. 
Takeda Provides Update on TAK-994 Clinical Program.
Accessed on 14/04/2023. Modified on 14/04/2023. takeda.com, https://www.takeda.com/newsroom/newsreleases/2021/takeda-provides-update-on-tak-994-clinical-program