• Bioorg. Med. Chem. Lett. · Nov 2010

    Comparative Study

    Neurosteroid analogues. 15. A comparative study of the anesthetic and GABAergic actions of alphaxalone, Δ16-alphaxalone and their corresponding 17-carbonitrile analogues.

    • Achintya K Bandyopadhyaya, Brad D Manion, Ann Benz, Amanda Taylor, Nigam P Rath, Alex S Evers, Charles F Zorumski, Steven Mennerick, and Douglas F Covey.
    • Department of Developmental Biology, Campus Box 8103, Washington University in St. Louis, School of Medicine, 660 S. Euclid Ave., St. Louis, MO 63110, USA.
    • Bioorg. Med. Chem. Lett. 2010 Nov 15; 20 (22): 6680-4.

    AbstractAlphaxalone, a neuroactive steroid containing a 17β-acetyl group, has potent anesthetic activity in humans. This pharmacological activity is attributed to this steroid's enhancement of γ-amino butyric acid-mediated chloride currents at γ-amino butyric acid type A receptors. The conversion of alphaxalone into Δ(16)-alphaxalone produces an analogue that lacks anesthetic activity in humans and that has greatly diminished receptor actions. By contrast, the corresponding 17β-carbonitrile analogue of alphaxalone and the Δ(16)-17-carbonitrile analogue both have potent anesthetic and receptor actions. The differential effect of the Δ(16)-double bond on the actions of alphaxalone and the 17β-carbonitrile analogue is accounted for by a differential effect on the orientation of the 17-acetyl and 17-carbonitrile substituents.Copyright © 2010 Elsevier Ltd. All rights reserved.

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