13-07127. Pazinaclone [Archived]

Nomenclature

CAS number: 103255-66-9
8-[[2-(7-Chloro-1,8-naphthyridin-2-yl)-2,3-dihydro-3-oxo-1H-isoindol-1-yl]acetyl]-1,4-dioxa-8-azaspiro[4.5]decane; (±)-2-(7-chloro-1,8-naphthyridin-2-yl)-3-[(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)carbonylmethyl]isoindolin-1-one; DN-2327.
C25H23ClN4O4; mol wt 478.93.
C 62.70%, H 4.84%, Cl 7.40%, N 11.70%, O 13.36%.

Description and references

Non-benzodiazepine exhibiting mixed agonist/antagonist effects with benzodiazepine receptors; activity resides primarily in the (S)-enantiomer. Prepn: G. Goto, Y. Saji, EP 174858; eidem, US 4695572 (1986, 1987 both to Takeda). Pharmacologic profile: T. Wada, N. Fukuda, Psychopharmacology 103, 314 (1991). HPLC determn in human plasma and urine, of racemate and/or its metabolites: Z. Hussein et al., J. Chromatogr. 613, 105 (1993); of enantiomers and/or their metabolites: eidem, ibid. 113. Clinical pharmacokinetics of racemate and its enantiomers: Z. Hussein et al., Br. J. Clin. Pharmacol. 36, 357 (1993). Clinical evaluation and abuse liability of racemate: G. K. Mumford et al., Exp. Clin. Psychopharmacol. 3, 39 (1995).

Chemical structure

Properties

Colorless crystals from methylene chloride/ethyl acetate, mp 238-239°.

Therapeutic Category

Anxiolytic.

Keywords

Anxiolytic

Status

This monograph has been retired and is no longer subject to revision or update.