Literature DB >> 35491852

Evaluation of Tebipenem Hydrolysis by β-Lactamases Prevalent in Complicated Urinary Tract Infections.

Zhizeng Sun1, Lynn Su1, Nicole Cotroneo2, Ian Critchley2, Michael Pucci2, Akash Jain2, Timothy Palzkill1.   

Abstract

Tebipenem pivoxil is the first orally available carbapenem antibiotic and has been approved in Japan for treating ear, nose, and throat and respiratory infections in pediatric patients. Its active moiety, tebipenem, has shown potent antimicrobial activity in vitro against clinical isolates of Enterobacterales species from patients with urinary tract infections (UTIs), including those producing extended-spectrum β-lactamases (ESBLs) and/or AmpC β-lactamase. In the present study, tebipenem was tested for stability to hydrolysis by a set of clinically relevant β-lactamases, including TEM-1, AmpC, CTX-M, OXA-48, KPC, and NDM-1 enzymes. In addition, hydrolysis rates of other carbapenems, including imipenem, meropenem, and ertapenem, were determined for comparison. It was found that, similar to other carbapenems, tebipenem was resistant to hydrolysis by TEM-1, CTX-M, and AmpC β-lactamases but was susceptible to hydrolysis by KPC, OXA-48, and NDM-1 enzymes with catalytic efficiency values (kcat/Km) ranging from 0.1 to 2 × 106 M-1s-1. This supports the reported results of antimicrobial activity of tebipenem against ESBL- and AmpC-producing but not carbapenemase-producing Enterobacterales isolates. Considering that CTX-M and AmpC β-lactamases represent the primary determinants of multidrug-resistant complicated UTIs (cUTIs), the stability of tebipenem to hydrolysis by these enzymes supports the utility of its prodrug tebipenem, tebipenem pivoxil hydrobromide (TBP-PI-HBr), as an oral therapy for adult cUTIs.

Entities:  

Keywords:  AmpC; ESBL; SPR994; cUTI; carbapenems; tebipenem; tebipenem pivoxil hydrobromide; β-lactamases

Mesh:

Substances:

Year:  2022        PMID: 35491852      PMCID: PMC9112902          DOI: 10.1128/aac.02396-21

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  19 in total

1.  Structural Basis for Different Substrate Profiles of Two Closely Related Class D β-Lactamases and Their Inhibition by Halogens.

Authors:  Vlatko Stojanoski; Dar-Chone Chow; Bartlomiej Fryszczyn; Liya Hu; Patrice Nordmann; Laurent Poirel; Banumathi Sankaran; B V Venkataram Prasad; Timothy Palzkill
Journal:  Biochemistry       Date:  2015-05-14       Impact factor: 3.162

2.  Pharmacodynamics of Tebipenem: New Options for Oral Treatment of Multidrug-Resistant Gram-Negative Infections.

Authors:  Laura McEntee; Adam Johnson; Nicola Farrington; Jennifer Unsworth; Aaron Dane; Akash Jain; Nicole Cotroneo; Ian Critchley; David Melnick; Thomas Parr; Paul G Ambrose; Shampa Das; William Hope
Journal:  Antimicrob Agents Chemother       Date:  2019-07-25       Impact factor: 5.191

3.  Antibiotic coresistance in extended-spectrum-beta-lactamase-producing Enterobacteriaceae and in vitro activity of tigecycline.

Authors:  María-Isabel Morosini; María García-Castillo; Teresa M Coque; Aránzazu Valverde; Angela Novais; Elena Loza; Fernando Baquero; Rafael Cantón
Journal:  Antimicrob Agents Chemother       Date:  2006-08       Impact factor: 5.191

Review 4.  Urinary tract infections: epidemiology, mechanisms of infection and treatment options.

Authors:  Ana L Flores-Mireles; Jennifer N Walker; Michael Caparon; Scott J Hultgren
Journal:  Nat Rev Microbiol       Date:  2015-04-08       Impact factor: 60.633

Review 5.  Carbapenems: past, present, and future.

Authors:  Krisztina M Papp-Wallace; Andrea Endimiani; Magdalena A Taracila; Robert A Bonomo
Journal:  Antimicrob Agents Chemother       Date:  2011-08-22       Impact factor: 5.191

6.  Characterization of purified New Delhi metallo-β-lactamase-1.

Authors:  Pei W Thomas; Min Zheng; Shanshan Wu; Hua Guo; Dali Liu; Dingguo Xu; Walter Fast
Journal:  Biochemistry       Date:  2011-11-01       Impact factor: 3.162

7.  A triple mutant in the Ω-loop of TEM-1 β-lactamase changes the substrate profile via a large conformational change and an altered general base for catalysis.

Authors:  Vlatko Stojanoski; Dar-Chone Chow; Liya Hu; Banumathi Sankaran; Hiram F Gilbert; B V Venkataram Prasad; Timothy Palzkill
Journal:  J Biol Chem       Date:  2015-02-20       Impact factor: 5.157

8.  Characterization of a new metallo-beta-lactamase gene, bla(NDM-1), and a novel erythromycin esterase gene carried on a unique genetic structure in Klebsiella pneumoniae sequence type 14 from India.

Authors:  Dongeun Yong; Mark A Toleman; Christian G Giske; Hyun S Cho; Kristina Sundman; Kyungwon Lee; Timothy R Walsh
Journal:  Antimicrob Agents Chemother       Date:  2009-09-21       Impact factor: 5.191

Review 9.  Tebipenem, the first oral carbapenem antibiotic.

Authors:  Akash Jain; Luke Utley; Thomas R Parr; Thomas Zabawa; Michael J Pucci
Journal:  Expert Rev Anti Infect Ther       Date:  2018-07-27       Impact factor: 5.091

10.  Safety, Pharmacokinetics, and Food Effect of Tebipenem Pivoxil Hydrobromide after Single and Multiple Ascending Oral Doses in Healthy Adult Subjects.

Authors:  Paul B Eckburg; Akash Jain; Susannah Walpole; Grayson Moore; Luke Utley; Erika Manyak; Aaron Dane; David Melnick
Journal:  Antimicrob Agents Chemother       Date:  2019-08-23       Impact factor: 5.191

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