Biotransformation of 20(R/S)-glucopyranosyloxy methylprednisolonates and their evaluation as colonic mucosa-specific pro-antedrugs

Toshikiro Kimura, Takehiro Yamagucki, Kumi Usuki, Yuji Kurosaki, Taiji Nakayama, Yukiko Fujiwara, Katsuo Unno, Toshio Suzuki

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Abstract

Biotransformation of 20 (R/S)-glucopyranosyloxy methylprednisoionates and their evaluation as colonic mucosa-specific pro-antedrugs The fate of 2-0 (R/S) glucopyrauosyloxy methylprednisolonates after the oral administration was examined in rats and guinea-pigs. The glycosides were stable in the small-intestinal contents, but the glycoside bonds were cleaved by the action of bacteria in the large-intestinal contents to release methyl 20(R/S)-dihydroprednisolonates, which were rapidly hydrolyzed to inactive carboxylates in the plasma. The high recovery of the glycosides and the aglycons in the large-intestinal contents after intrajejunal administration of 20(R/S)-glucopyranosyloxy methylprednisolonates in guinea-pigs proved the glycosides to he poorly absorbed from the small intestine. These results suggest that 20 (R/S)-glucopyranosyloxy methylprednisolonates may be orally effective pro-antedrugs, which express the anti-inflammatory activity specifically in the colonic mucosa with no systemic effect.

Original languageEnglish
Pages (from-to)375-379
Number of pages5
JournalDrug Delivery System
Volume6
Issue number5
DOIs
Publication statusPublished - 1991

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Glycosides
Biotransformation
Gastrointestinal Contents
Mucous Membrane
Guinea Pigs
Small Intestine
Oral Administration
Anti-Inflammatory Agents
Bacteria

Keywords

  • 20(R/S)-glucopyranosyloxy methylprednisolonates
  • chemical drug delivery system
  • colonic bacteria
  • colonic mucosa
  • pro-antedrug

ASJC Scopus subject areas

  • Pharmaceutical Science

Cite this

Biotransformation of 20(R/S)-glucopyranosyloxy methylprednisolonates and their evaluation as colonic mucosa-specific pro-antedrugs. / Kimura, Toshikiro; Yamagucki, Takehiro; Usuki, Kumi; Kurosaki, Yuji; Nakayama, Taiji; Fujiwara, Yukiko; Unno, Katsuo; Suzuki, Toshio.

In: Drug Delivery System, Vol. 6, No. 5, 1991, p. 375-379.

Research output: Contribution to journalArticle

Kimura, Toshikiro ; Yamagucki, Takehiro ; Usuki, Kumi ; Kurosaki, Yuji ; Nakayama, Taiji ; Fujiwara, Yukiko ; Unno, Katsuo ; Suzuki, Toshio. / Biotransformation of 20(R/S)-glucopyranosyloxy methylprednisolonates and their evaluation as colonic mucosa-specific pro-antedrugs. In: Drug Delivery System. 1991 ; Vol. 6, No. 5. pp. 375-379.
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