Talampicillin

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

Talampicillin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.051.194
Chemical and physical data
FormulaC24H23N3O6S
Molar mass481.52092 g/mol g·mol−1
3D model (JSmol)
 NY (what is this?)  (verify)

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.

Talampicillin synthesis:[1][2][3][4]

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).

References
  1. I. Isaka, K. Nakano, T. Kashiwagi, A. Koda, H.Horiguchi, H. Matsui, K. Takahashi and M.Murakami, Chem. and Pharm. Bull., 24, 102 (1976).
  2. J. P. Clayton, M. Cole, S. W. Elson, H. Ferres, J. C. Hanson, L. W. Mizen and R. Sutherland, J.Med. Chem., 19, 1385 (1976).
  3. H. Ferres, M. P. Clayton, DE 2228012; eidem, US 3860579 (1972, 1975 both to Beecham).
  4. See also: M. Murakami et al., US 3951954 (1976 to Yamanouchi).


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.