Tebipenem Pivoxil is a pivaloyloxymethyl ester prodrug form of Tebipenem, a broad-spectrum, 1-beta-methylcarbapenem antibiotic. Tebipenem is a β-lactam antibiotic which inhibits β-lactamase in a concentration-dependent manner. Tebinenem, like other beta-lactams, has high specificity and low toxicity and makes them useful against Gram-positive and Gram-negative bacteria. Tebipenem was developed to combat bacteria such as methicillin-resistant Staphylococcus aureus, that had acquired resistance to common antibiotics. The compound has a 1-(1,3-thiazolin-2-yl) azetidin-3-ylthio group at the C-2 position. Tebipenem Pivoxil is metabolized by carboxylesterase in intestinal epithelial cells to form tebipenem, the main metabolite.
We also offer:
- Tebipenem Hydrate (T162)
| Mechanism of Action |
β-lactams interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to β-lactams is commonly due to cells containing plasmid encoded β-lactamases. |
| Spectrum | Tebipenem is active against Gram-positive and Gram-negative bacteria. It is also active against methicillin-resistant strains of Staphyloccoccus aureus and S. epidermidis and penicillin-resistant Streptoccos pneumoniae strains. |
| Microbiology Applications | Tebipenem is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include:
Carbapenems are active against enterobacteria producing extended-spectrum beta-lactamase (ESBL) and AmpC enzymes since they are not affected by these resistance mechanisms (Jain et al, 2018). |
| Molecular Formula | C22H31N3O6S2 |
| Eukaryotic Cell Culture Applications | Tebipenem Pivoxil is metabolized by carboxylesterase in intestinal epithelial cells to produce the active form Tebipenem. Authors studied transport mechisms and found that its uptake by Caco-2 cells was decreased by ATP-depletion and reducing the temperature to 4°C, suggesting the contribution of carrier-mediated transport mechanisms. Researchers found it has high intestinal apical membrane permeability via plural intestinal transport routes, including the uptake transporters like OATP1A2 and OATP2B1 in addition to simple diffusion (Kato et al, 2010). |
| References |
Cielecka-Piontek J, Zalewski P and Paczkowska M (2015) The chromatographic approach to kinetic studies of Ttebipenem Pivoxil. J. Chromatogr. Sci. 53(2):325-330 Hazra S, Xu H, Blanchard JS (2014) Tebipenem, a new carbapenem antibiotic, is a slow substrate that inhibits the β-lactamase from Mycobacterium tuberculosis. Biochem. 53(22):3671-3678 PMID 24846409 Jain A, Utley L, Parr TR, Zabawa T, Pucci MJ (2018) Tebipenem, the first oral carbapenem antibiotic. Expert Rev Anti Infect Ther. 16(7):513-522 PMID 30014729 Kato K et al (2010) Intestinal absorption mechanism of tebipenem pivoxil, a novel oral carbapenem: involvement of human OATP family in apical membrane transport. Mol Pharm.7(5):1747-1756 PMID 20735088 Mendes RE et al (2023) Contemporary evaluation of Tebipenem in vitro activity against Enterobacterales clinical isolates causing urinary tract Iifections in US medical centers (2019-2020). Microbiol Spectr. 11(1):e0205722 PMID 36625644 |
