Talampicillin

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Talampicillin
Talampicillin.png
Systematic (IUPAC) name
3-oxo-1,3-dihydro-2-benzofuran-1-yl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 47747-56-8 YesY
ATC code J01CA15
PubChem CID 5373
ChemSpider 64529 N
UNII 29OJI73DPC N
ChEMBL CHEMBL1322719 N
Chemical data
Formula C24H23N3O6S
Molar mass 481.52092 g/mol
 NYesY (what is this?)  (verify)

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.

Synthesis[edit]

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[edit]

  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).