Synthesis and Evaluation of Carbamate Prodrugs of a Phenolic Compound

• Igarashi Yasushi

  R&D Division, Tsumura & Co. Department of Clinical Pharmacy, Graduate School of Natural Science and Technology, Kanazawa University

• Yanagisawa Erika

  R&D Division, Tsumura & Co.

• Ohshima Toshihiro

  R&D Division, Tsumura & Co.

• Takeda Shuichi

  R&D Division, Tsumura & Co.

• Aburada Masaki

  Research Institute of Pharmaceutical Sciences, Musashino University

• Miyamoto Ken-ichi

  Department of Clinical Pharmacy, Graduate School of Natural Science and Technology, Kanazawa University

抄録

A series of carbamates of the phenolic compound 1 were prepared and evaluated in vivo as its prodrug. Each carbamate was orally administered to rats, and plasma concentrations of the parent compound 1 were measured with the passage of time. We judged which carbamate was suitable for the prodrug of 1 from both the AUC value of 1 and absence of the carbamate in plasma. The AUC value of 1 after oral administration of 2b was approximately 40-fold higher than that for an administration of 1, and the bioconversion from 2b to 1 was excellent. As a whole, di-substituted carbamates resulted in higher plasma concentrations of 1 than did mono-substituted ones. However di-substituted carbamates were almost always detected in plasma. As a result, we found that the ethycarbamoyl derivative 2b demonstrates the best prodrug property in this series.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 55 (2), 328-333, 2007

  公益社団法人 日本薬学会

キーワード

• prodrug
• carbamate
• capillarisin

詳細情報

• CRID: 1390282679145981696
• NII論文ID: 110006162446
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.55.328
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 8616329
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I8616329
• Web Site: http://www.jstage.jst.go.jp/article/cpb/55/2/55_2_328/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可