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Tebipenem pivoxil is an orally available ester prodrug of the broad spectrum carbapenem antibiotic Tebipenem. Tebipenem is a potent inhibitor of multiple penicillin-binding proteins (PBPs) but primarily a Gram-negative PBP 2 inhibitor. It react with the highly active beta-lactamase to form enzyme-drug covalent complex that is hydrolyzed extremely slowly.
| Cas No. | 161715-24-8 |
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| Purity | ≥99% |
| Formula | C22H31N3O6S2 |
| Formula Wt. | 497.6 |
| Chemical Name | Tebipenem pivoxil |
| IUPAC Name | 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate |
| Synonym | Orapenem; TBPM-PI; L-084; (4R,5S,6S)-(Pivaloyloxy)methyl 3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; 2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate |
| Store Temp | -20°C |
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| MSDS | |
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| Info Sheet |
E. Lacasse, E. Brouillette, A. Larose, e tal. In Vitro Activity of Tebipenem (SPR859) against Penicillin-Binding Proteins of Gram-Negative and Gram-Positive Bacteria. Antimicrob Agents Chemother. 63(4):e02181-18 2019.
S. Hazra, H. Xu, and J. S. Blanchard, Tebipenem, a new carbapenem antibiotic, is a slow substrate that inhibits the β-lactamase from Mycobacterium tuberculosis. Biochemistry.2014; 53(22):3671-8.