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Xenobiotica
the fate of foreign compounds in biological systems
Volume 42, 2012 - Issue 3
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General Xenobiochemistry

Microbial production of phase I and phase II metabolites of midazolam

, , , &
Pages 285-293 | Received 23 Jul 2011, Accepted 07 Sep 2011, Published online: 24 Oct 2011
 

Abstract

  1. Midazolam, a potent benzodiazepine derivative and a typical substrate of CYP3A4/3A5, is essentially metabolized in human into 1′-hydroxymidazolam, then eliminated as the corresponding phase II metabolite, the 1′-O-β-d-glucuronide derivative.

  2. A high yield alternative to the current multistep synthesis of 1′-hydroxymidazolam is described, using a biotransformation of midazolam by a fungal microorganism, Beauveria bassiana.

  3. The corresponding phase II metabolite, 1′-hydroxymidazolam-1′-O-β-d-glucuronide, has been then prepared by chemical synthesis (3 steps, 20% yield), or by microbial glucuronidation (one step, 20% yield) using a Streptomyces sp. strain.

  4. The use of the same Streptomyces strain allows a direct and expeditive synthesis of the same glucuronide conjugate from midazolam itself in an advantageous 17% yield.

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