Talampicillin

Talampicillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01CA15 (WHO) ;
Identifiers
	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;
CAS Number	47747-56-8 ;
PubChem CID	5373;
ChemSpider	64529 ;
UNII	29OJI73DPC;
ChEMBL	ChEMBL1322719 ;
CompTox Dashboard (EPA)	DTXSID1048540 ;
ECHA InfoCard	100.051.194
Chemical and physical data
Formula	C24H23N3O6S
Molar mass	481.52 g·mol−1
3D model (JSmol)	Interactive image;
	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. 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.

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).

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References

I. Isaka, K. Nakano, T. Kashiwagi, A. Koda, H.Horiguchi, H. Matsui, K. Takahashi and M.Murakami, Chem. and Pharm. Bull., 24, 102 (1976).
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).
H. Ferres, M. P. Clayton, DE 2228012; eidem, US 3860579 (1972, 1975 both to Beecham).
See also: M. Murakami et al., US 3951954 (1976 to Yamanouchi).

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[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).