Biopharmaceutical Study of Inclusion Complexes. I. Pharmaceutical Advantages of Cyclodextrin Complexes of Bencyclane Fumarate

Keiji Fujioka, Yuji Kurosaki, Shigeji Satc, Tetsuo Noguchi, Takeshi Noguchi, Yoshiya Yamahira

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Complexes of bencyclane fumarate (Ben) with cyclodextrins (CDs) were newly prepared and their characteristics were studied from a pharmaceutical viewpoint. The results of differential scanning calorimetry (DSC), X-ray diffractometry and thin-layer chromatography (TLC) were consistent with the formation of inclusion complexes. Water solubility of Ben-CDs were 2- to 8-fold lager than that of Ben. The stability of Ben in acidic media (pH 1.2) was considerably improved by complex formation with β-CD or y-CD. Apparent first-order rate constants [h-1] of hydrolysis of Ben were 6.5xl0-2 5.5xl0-2 l.OxlO-2 and 1.7x l0-2 for Ben, Ben-a-CD, Ben-β-CD and Ben-y-CD, respectively. The intrinsic bitter taste of Ben was significantly reduced by inclusion complexation with CDs. Thus, there are clear pharmaceutical advantages of Ben-CD compared with Ben. In addition, a novel animal test method, which is helpful for studying astringent bitter-tasting drugs, is proposed.

Original languageEnglish
Pages (from-to)2416-2423
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume31
Issue number7
DOIs
Publication statusPublished - Aug 1983
Externally publishedYes

Keywords

  • bencyclane fumarate
  • bitterness
  • cyclodextrin
  • inclusion complex
  • stability

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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