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Benzodiazepine drug
SH-053-R-CH3-2′F
(R )-8-ethynyl-6-(2-fluorophenyl)-4-methyl-4H -2,5,10b -triaza-benzo[e ]azulene-3-carboxylic acid ethyl ester
CAS Number
PubChem
CID
ChemSpider
CompTox Dashboard (
EPA )
Formula C 23 H 18 F N 3 O 2
Molar mass 387.414 g·mol−1 3D model (
JSmol )
Fc2ccccc2C1=NC(C)c3c(C(=O)OCC)ncn3-c(cc4)c1cc4C#C
InChI=1S/C23H18FN3O2/c1-4-15-10-11-19-17(12-15)20(16-8-6-7-9-18(16)24)26-14(3)22-21(23(28)29-5-2)25-13-27(19)22/h1,6-14H,5H2,2-3H3/t14-/m1/s1
Key:NGYKELBMVXBFSM-CQSZACIVSA-N
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
^ Savić MM, Huang S, Furtmüller R, Clayton T, Huck S, Obradović DI, et al. (January 2008).
"Are GABAA receptors containing alpha5 subunits contributing to the sedative properties of benzodiazepine site agonists?" . Neuropsychopharmacology . 33 (2): 332–339.
doi :
10.1038/sj.npp.1301403 .
PMID
17392731 .
^ Savić MM, Clayton T, Furtmüller R, Gavrilović I, Samardzić J, Savić S, et al. (May 2008).
"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.
doi :
10.1016/j.brainres.2008.02.020 .
PMC
2577822 .
PMID
18394590 .
^ Stamenić TT, Poe MM, Rehman S, Santrač A, Divović B, Scholze P, et al. (November 2016).
"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.
doi :
10.1016/j.ejphar.2016.09.016 .
PMC
5107132 .
PMID
27639297 .
^
CA 3016491 , 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."
^ Prevot TD, Li G, Vidojevic A, Misquitta KA, Fee C, Santrac A, et al. (April 2019).
"Novel Benzodiazepine-Like Ligands with Various Anxiolytic, Antidepressant, or Pro-Cognitive Profiles" . Molecular Neuropsychiatry . 5 (2): 84–97.
doi :
10.1159/000496086 .
PMC
6528097 .
PMID
31192221 .
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