Talampicillin

Talampicillin

File:Talampicillin.svg
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 checkY
PubChem CID	5373
ChemSpider	64529 ☒N
UNII	29OJI73DPC
ChEMBL	ChEMBL1322719 ☒N
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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 ☒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

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.

File:Talampicillin synthesis.svg

Talampicillin synthesis:

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).