AS-924, a Novel Orally Active Bifunctional Prodrug of Ceftizoxime. Synthesis and Relationship between Physicochemical Properties and Oral Absorption.
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説明
Ceftizoxime (CZX), a parenteral cephalosporin, has potent and broad antibacterial activity. To improve its oral absorption, we synthesized a series of monofunctional and bifunctional prodrugs of CZX. In rabbits, urinary recovery after oral administration of CZX was improved by esterification of the carboxyl group at the C-4 position with various lipophilic moieties (monofunctional prodrugs), and was further increased by introduciton of a hydrophilic L-alanine to the amino group on the thiazole ring at the C-7 position (bifuncional prodrugs). Least-squares analysis showed good parabolic correlatoins between log P and urinary recovery for monofunctional and bifunctional prodrugs, respectively. AS-924, a bifunctional prodrug with a pivaloyloxymethyl and L-alanyl moiety had the best balance of lipophilicity and water-solubility for oral absorption among the prodrugs synthesized.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 47 (8), 1081-1088, 1999
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390001204161539200
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- NII論文ID
- 130003773926
- 110003617375
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DyaK1MXlsVOgt7Y%3D
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 4834566
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- PubMed
- 10478463
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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- JaLC
- NDLサーチ
- Crossref
- PubMed
- CiNii Articles
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- 使用不可