Lirequinil

Chemical compound From Wikipedia, the free encyclopedia

Lirequinil (development code Ro 41-3696) is a nonbenzodiazepine hypnotic drug which binds to benzodiazepine sites on the GABAA receptor.[1] In human clinical trials, lirequinil was found to have similar efficacy to zolpidem, with less side effects such as clumsiness and memory impairment. However it was also much slower acting than zolpidem, with peak plasma concentrations not reached until 2.5 hours after oral administration, and its O-desethyl metabolite Ro41-3290 is also active with a half-life of 8 hours.[2][3][4][5] This meant that while effective as a hypnotic, lirequinil failed to prove superior to zolpidem due to producing more next-day sedation, and it has not been adopted for clinical use. It was developed by a team at Hoffmann-La Roche in the 1990s.[6]

Active metabolite Ro41-3290
Other namesRo 41-3696; Ro41-3696; RO-413696; RO413696
Routes of
administrationOral[1]
ATC code
  • None
CAS Number
Quick facts Clinical data, Other names ...
Lirequinil
Clinical data
Other namesRo 41-3696; Ro41-3696; RO-413696; RO413696
Routes of
administration		Oral[1]
ATC code
  • None
Identifiers
  • 10-chloro-1-[(3S)-3-ethoxypyrrolidine-1-carbonyl]-3-phenyl-6,7-dihydrobenzo[a]quinolizin-4-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H25ClN2O3
Molar mass448.95 g·mol−1
3D model (JSmol)
  • CCO[C@H]1CCN(C1)C(=O)C2=C3C4=C(CCN3C(=O)C(=C2)C5=CC=CC=C5)C=CC(=C4)Cl
  • InChI=1S/C26H25ClN2O3/c1-2-32-20-11-12-28(16-20)25(30)23-15-22(17-6-4-3-5-7-17)26(31)29-13-10-18-8-9-19(27)14-21(18)24(23)29/h3-9,14-15,20H,2,10-13,16H2,1H3/t20-/m0/s1 ☒N
  • Key:CBSWRAUYCIIUEI-FQEVSTJZSA-N ☒N
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