Talampicillin

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Talampicillin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 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
JSmol)
  • O=C(OC2OC(=O)c1ccccc12)[C@@H]4N5C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]5SC4(C)C
  • InChI=1S/C24H23N3O6S/c1-24(2)17(22(31)33-23-14-11-7-6-10-13(14)21(30)32-23)27-19(29)16(20(27)34-24)26-18(28)15(25)12-8-4-3-5-9-12/h3-11,15-17,20,23H,25H2,1-2H3,(H,26,28)/t15-,16-,17+,20-,23?/m1/s1 ☒N
  • Key:SOROUYSPFADXSN-SUWVAFIASA-N ☒N
 ☒NcheckY (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. It should be avoided in Liver diseases

Synthesis

pharmacodynamic
characteristics, and one of these is talampicillin.

Talampicillin synthesis:[1][2][3][4][5]

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

  1. PMID 1269054
    .
  2. PMID 826629
    .
  3. ^ DE 2228012, Ferres H, Clayton MP, "Phthalide penicillin ester intermediates", issued 1972, assigned to Beecham 
  4. ^ US 3860579, Ferres H, Clayton MP, "Phthalide Peniclillin Ester and Salts", issued 1975, assigned to Beecham 
  5. ^ US 3951954, Murakami, "Novel oxofuryl ester derivatives of penicillin and cephalosporin", issued 1976, assigned to Yamanouchi 


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