Hydrolysis of idoxuridine

✍ Scribed by Louis J. Ravin; Charles A. Simpson; Alfred F. Zappala; John J. Gulesich

• Publisher: John Wiley and Sons
• Year: 1964
• Tongue: English
• Weight: 243 KB
• Volume: 53
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600530917

✦ Synopsis

Data are presented for the hydrolytic degradation of idoxuridine (5-iodo-2 '-deoxyuridine) in aqueous solution over a wide range of hydrogen ion concentration (pH 1.3 to 12.0). The over-all reaction rate was experimentally equal to R, '' K, + IH+l idoxuridine at p H 6.0 was found to be approximately 25 Kcal. per mole. A probable pathway for the hydrolysis of idoxuridine in acid and alkaline solution is discussed. lH+l + + R3 K* [OH-]. The heat of activation for the hydrolysis of IH' I + K a K, K. + IH+l DOXURIDINE (.5-iado-:!'-deoxyuridine) has been reported

to be an effective chemotherapeutic agent for the treatment of herpetic keratitis (1). Its rhemical, biological, and pharmaceutical properties have been described previously (2). Results of clinical studies have also been reported (3, 4). There are several reports that discuss the enzymatic pathways for the metabolism of idoxuridine and related prirnidines (5-7). However, the literature is lacking in information concerning its chemical degradation. The scope of the present work was concerned with the hydrolytic degradation of idoxuridine in acidic and alkaline solution.