Talampicillin

Talampicillin

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
ATC code	J01CA15 (WHO)
PubChem	CID 5373
ChemSpider	64529
UNII	29OJI73DPC
ChEMBL	CHEMBL1322719
Chemical data
Formula	C24H23N3O6S
Molar mass	481.52092 g/mol
SMILES O=C(OC2OC(=O)c1ccccc12)[C@@H]4N5C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]5SC4(C)C
InChI 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 Key:SOROUYSPFADXSN-SUWVAFIASA-N
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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.

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).