Lirequinil

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Lirequinil
Clinical data
ATC code
  • none
Identifiers
  • 10-chloro-1-[(3S)-3-ethoxypyrrolidine-1-carbonyl]-3-phenyl-6,7-dihydrobenzo[a]quinolizin-4-one
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
 ☒NcheckY (what is this?)  (verify)

Lirequinil (Ro41-3696) is a

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.[1][2][3][4] 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.[5]

Active metabolite Ro41-3290

References

  1. S2CID 20456430
    .
  2. S2CID 11960902
    .
  3. PMID 11095577
    .
  4. S2CID 21588500
    .
  5. ^ US Patent 5561233 Process for the preparation of an intermediate of a benzo[a]quinolizinone derivative
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