Chemistry:Talampicillin
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| Formula | C24H23N3O6S |
| Molar mass | 481.52 g·mol−1 |
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Talampicillin is a beta lactam antibiotic from the penicillin family. It is an acid stable prodrug that was administered orally. It is not approved by the FDA for use in the United States. It should be avoided in Liver diseases
Synthesis
Ampicillin remains the penicillin of choice for many infections because of its oral activity and good potency against Gram-negative bacteria. A number of prodrugs have been examined in attempts to improve upon the pharmacodynamic characteristics, and one of these is talampicillin.
One synthesis involved protecting the primary amino group of ampicillin (1) as the enamine with ethyl acetoacetate (2). THis was then esterified by reaction with 3-bromopthalide (3), and the enamine was carefully hydrolyzed with dilute HCl in acetonitrile to produce talampicillin (4).[citation needed]
References
- ↑ "Lactol esters of ampicillin". Chemical & Pharmaceutical Bulletin 24 (1): 102–7. January 1976. doi:10.1248/cpb.24.102. PMID 1269054.
- ↑ "Preparation, hydrolysis, and oral absorption of lactonyl esters of penicillins". Journal of Medicinal Chemistry 19 (12): 1385–91. December 1976. doi:10.1021/jm00234a007. PMID 826629.
- ↑ Ferres H, Clayton MP, "Phthalide penicillin ester intermediates", DE patent 2228012, issued 1972, assigned to Beecham
- ↑ Ferres H, Clayton MP, "Phthalide Peniclillin Ester and Salts", US patent 3860579, issued 1975, assigned to Beecham
- ↑ Murakami, "Novel oxofuryl ester derivatives of penicillin and cephalosporin", US patent 3951954, issued 1976, assigned to Yamanouchi
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