Chemistry:SH-053-R-CH3-2′F
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| Formula | C23H18FN3O2 |
| Molar mass | 387.414 g·mol−1 |
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SH-053-R-CH3-2′F is a drug used in scientific research which is a benzodiazepine derivative. It produces some of the same effects as other benzodiazepines, but is much more subtype-selective than most other drugs of this class, having high selectivity, binding affinity and efficacy at the α5 subtype of the GABAA receptor. This gives much tighter control of the effects produced, and so while SH-053-R-CH3-2′F retains sedative and anxiolytic effects, it does not cause ataxia at moderate doses.[1] SH-053-R-CH3-2′F also blocks the nootropic effects of the α5-selective inverse agonist PWZ-029, so amnesia is also a likely side effect.[2]
Replacement of the ester function by an amide, realized in analogs such as MP-III-022 and GL-II-73, improves selectivity, efficacy, and kinetic behavior.[3][4][5]
See also
References
- ↑ "Are GABAA receptors containing alpha5 subunits contributing to the sedative properties of benzodiazepine site agonists?". Neuropsychopharmacology 33 (2): 332–339. January 2008. doi:10.1038/sj.npp.1301403. PMID 17392731.
- ↑ "PWZ-029, a compound with moderate inverse agonist functional selectivity at GABA(A) receptors containing alpha5 subunits, improves passive, but not active, avoidance learning in rats". Brain Research 1208: 150–159. May 2008. doi:10.1016/j.brainres.2008.02.020. PMID 18394590.
- ↑ "Ester to amide substitution improves selectivity, efficacy and kinetic behavior of a benzodiazepine positive modulator of GABAA receptors containing the α5 subunit". European Journal of Pharmacology 791: 433–443. November 2016. doi:10.1016/j.ejphar.2016.09.016. PMID 27639297.
- ↑ Cook JM, Li G, Poe M, Savic M, Sibille E, "Treatment of cognitive and mood symptoms in neurodegenerative and neuropsychiatric disorders with alpha5-containing gabaa receptor agonists.", CA patent 3016491
- ↑ "Novel Benzodiazepine-Like Ligands with Various Anxiolytic, Antidepressant, or Pro-Cognitive Profiles". Molecular Neuropsychiatry 5 (2): 84–97. April 2019. doi:10.1159/000496086. PMID 31192221.
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