SH-I-048A

SH-I-048A (SH-i-048A) is a benzodiazepine derivative related in structure to compounds such as flubromazepam and meclonazepam. SH-I-048A is described as a non subtype selective superagonist at the benzodiazepine site of GABA_A receptors,[1] with a binding affinity of 0.77nM at the α₁ subtype, 0.17nM at α₂, 0.38nM at α₃ and 0.11nM at α₅.[2] It has been used to study the functional differences between the different subtypes of the GABA_A receptor.[3][4]

SH-I-048A

Identifiers
IUPAC name (3S)-7-bromo-5-(2-fluorophenyl)-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one
CAS Number	872874-11-8
PubChem CID	49850464
ChemSpider	57381614
Chemical and physical data
Formula	C16H12BrFN2O
Molar mass	347.187 g·mol^−1
3D model (JSmol)	Interactive image
SMILES Fc3ccccc3C2=N[C@@H](C)C(=O)Nc1ccc(Br)cc12
InChI InChI=1S/C16H12BrFN2O/c1-9-16(21)20-14-7-6-10(17)8-12(14)15(19-9)11-4-2-3-5-13(11)18/h2-9H,1H3,(H,20,21)/t9-/m0/s1 Key:QEFZCKUXGLDPPT-VIFPVBQESA-N

See also

• GL-II-73
• QH-II-66
• SH-053-R-CH3-2'F

References

1. Obradović AL, Joksimović S, Poe MM, Ramerstorfer J, Varagic Z, Namjoshi O, Batinić B, Radulović T, Marković B, Roth BL, Sieghart W, Cook JM, Savić MM. "Sh-I-048A, an in vitro non-selective super-agonist at the benzodiazepine site of GABAA receptors: the approximated activation of receptor subtypes may explain behavioral effects". Brain Research. 1554.
2. Clayton T, Poe MM, Rallapalli S, Biawat P, Savić MM, Rowlett JK, et al. (2015). "A Review of the Updated Pharmacophore for the Alpha 5 GABA(A) Benzodiazepine Receptor Model". International Journal of Medicinal Chemistry. 2015: 430248. doi:10.1155/2015/430248. PMC 4657098. PMID 26682068.
3. Obradović LA, Joksimović S, Poe MM, Timić T, Cook JM, Savić MM (June 2014). "Delayed Behavioral Effects of SH–I–048A, a Novel Nonselective Positive Modulator of Gabaa Receptors, After Peripheral Nerve Injury in Rats". Acta Veterinaria. 64 (2): 189–99. doi:10.2478/acve-2014-0018.
4. Elgarf AA, Siebert DC, Steudle F, Draxler A, Li G, Huang S, et al. (August 2018). "Different Benzodiazepines Bind With Distinct Binding Modes to GABAA Receptors". ACS Chemical Biology. 13 (8): 2033–2039. doi:10.1021/acschembio.8b00144. PMC 6102643. PMID 29767950.