Tebipenem, the first oral carbapenem antibiotic

References

• Bush K, Bradford PA. β-Lactams and β-lactamase inhibitors: an overview. Cold Spring Harb Perspect Med. 2016;6(8). pil:a025247.
   PubMed Web of Science ®Google Scholar
• Bonomo RA. β-Lactamases: a focus on current challenges. Cold Spring Harb Perspect Med. 2017;7(1):a025239.
   PubMed Web of Science ®Google Scholar
• Drawz SM, Papp-Wallace KM, Bonomo RA. New β-lactamase inhibitors: a therapeutic renaissance in an MDR world. Antimicrob Agents Chemother. 2014;58:1835–1846.
   PubMed Web of Science ®Google Scholar
• Papp-Wallace KM, Bonomo RA. New β-Lactamase Inhibitors in the Clinic. Infect Dis Clin North Am. 2016;30:441–464.
   PubMed Web of Science ®Google Scholar
• Wong D, Van Duin D. Novel beta-lactamase inhibitors: unlocking their potential in therapy. Drugs. 2017;77:615–628.
   PubMed Web of Science ®Google Scholar
• Kahan JS, Kahan FM, Goegelman R, et al. Thienamycin, a new beta-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties. J Antibiot (Tokyo). 1979;32:1–12.
   PubMed Web of Science ®Google Scholar
• El-Gamal MI, Brahim I, Hisham N, et al. Recent updates of carbapenem antibiotics. Eur J Med Chem. 2017;131:185–195.
   PubMed Web of Science ®Google Scholar
• Papp-Wallace KM, Endimiani A, Taracila MA, et al. Carbapenems: past, present, and future. Antimicrob Agents Chemother. 2011;55:4943–4960.
   PubMed Web of Science ®Google Scholar
• Kumagai T, Tamai S, Abe T, et al. Current status of oral carbapenem development. Curr Med Chem – Anti-Infect Agents. 2002;1:1–14.
   Google Scholar
• Abe T, Hayashi K, Mihira A, et al. L-084, a new oral carbapenem: synthesis and structure-activity relationships of C2-substituted 1-methylcarbapenems. 38th Intersci Conf Antimicrob Agents Chemother (ICAAC) 1998; Abstract F-64.
   Google Scholar
• Yao Q, Wang J, Cui T, et al. Antibacterial properties of tebipenem pivoxil tablet, a new oral carbapenem preparation against a variety of pathogenic bacteria in vitro and in vivo. Molecules. 2016;21:62.
   PubMed Web of Science ®Google Scholar
• Spero Therapeutics Licenses Exclusive Rights to SPR994, a Novel Oral Carbapenem Being Studied for Use in Adults; 2017. [cited 2018 July 16]. Avaialble from: https://globenewswire.com/news-release/2017/10/10/1143681/0/en/Spero-Therapeutics-Licenses-Exclusive-Rights-to-SPR994-a-Novel-Oral-Carbapenem-Being-Studied-for-Use-in-Adults.html
   Google Scholar
• Rodríguez-Baño J, Gutiérrez-Gutiérrez B, Machuca I, et al. Treatment of infections caused by extended-spectrum-beta-lactamase-, AmpC-, and carbapenemase-producing Enterobacteriaceae. Clin Microbiol Rev. 2018;31:e00079–17.
   PubMed Web of Science ®Google Scholar
• Talan DA, Takhar SS, Krishnadasan A, et al. Fluoroquinolone–resistant and extended-spectrum β-lactamase-producing Escherichia coli infections in patients with pyelonephritis, United States (1). Emerg Infect Dis. 2016;22(9). DOI:10.3201/eid2209.160148
   PubMed Web of Science ®Google Scholar
• Hamilton-Miller JM. Chemical and microbiologic aspects of penems, a distinct class of beta-lactams: focus on faropenem. Pharmacotherapy. 2003;23:1497–1507.
   PubMed Web of Science ®Google Scholar
• Schurek KN, Wiebe R, Karlowsky JA, et al. Faropenem: review of a new oral penem. Expert Rev Anti Infect Ther. 2007;5:185–198.
   PubMed Web of Science ®Google Scholar
• Iterum Gains Important Support for Development of Novel Oral Antibiotic, Sulopenem; 2017. Available from: https://www.iterumtx.com/news/press-releases/detail/3/iterum-gains-important-support-for-development-of-novel. Accessed July 16, 2018.
   Google Scholar
• Dunne M, Dunzo E, Puttagunta S. A Phase 1 Study to Assess the Pharmacokinetics of Sulopenem Etzadroxil (PF-03709270). Open Forum Infectious Diseases. 2017;4:S525-S526. IDWeek 2017;Poster 1839
   Google Scholar
• Nakashima M, Morita J, Aizawa K. Pharamacokinetics and safety of oral carbapenem antibiotic tebipenem pivoxil tablets in healthy male volunteers. Jpn J Chemother. 2009;57(S–1):83–89.
   Google Scholar
• Iterum Therapeutics Form S-1 Registration Statement, U.S. Securities and Exchange Commission; 2018. [cited 2018 July 16]. Available from: https://www.nasdaq.com/markets/ipos/filing.ashx?filingid=12721016
   Google Scholar
• C-Scape: our next clinical candidate, an oral antibacterial to potentially address the growing problem of antimicrobial; 2018. [cited 2018 July 16]. Available from: http://www.achaogen.com/cscape/.
   Google Scholar
• Livermore DM, Mushtaq S, Nguyen T, et al. Strategies to overcome extended-spectrum β-lactamases (ESBLs) and AmpC β-lactamases in shigellae. Int J Antimicrob Agents. 2011;37:405–409.
   PubMed Web of Science ®Google Scholar
• Kato K, Shirasaka Y, Kuraoka E, et al. Intestinal absorption mechanism of tebipenem pivoxil, a novel oral carbapenem: involvement of human OATP family in apical membrane transport. Mol Pharm. 2010;7:1747–1756.
   PubMed Web of Science ®Google Scholar
• Cielecka-Piontek J, Zalewski P, Paczkowska M. The chromatographic approach to kinetic studies of tebipenem pivoxil. J Chromatogr Sci. 2015;53:325–330.
   PubMed Web of Science ®Google Scholar
• Zalewski P, Talaczyńska A, Korban P, et al. An approach to transfer methods from HPLC to UHPLC techniques in some carbapenems. Chromatographia. 2014;77:1483–1487.
   PubMed Web of Science ®Google Scholar
• Tran QT, Pearlstein RA, Williams S, et al. Structure-kinetic relationship of carbapenem antibacterials permeating through E. coli OmpC porin. Proteins. 2014;82:2998–3012.
   PubMed Web of Science ®Google Scholar
• Sauvage E, Terrak M. Glycosyltransferases and transpeptidases/penicillin-binding proteins: valuable targets for new antibacterials. Antibiotics (Basel). 2016;5(1):E12.
   PubMed Web of Science ®Google Scholar
• Yamada M, Watanabe T, Baba N, et al. Crystal structures of biapenem and tebipenem complexed with penicillin-binding proteins 2X and 1A from Streptococcus pneumoniae. Antimicrob Agents Chemother. 2008;52:2053–2060.
   PubMed Web of Science ®Google Scholar
• Hikida M, Itahashi K, Igarashi A, et al. In vitro antibacterial activity of LJC 11,036, an active metabolite of L-084, a new oral carbapenem antibiotic with potent antipneumococcal activity. Antimicrob Agents Chemother. 1999;43:2010–2016.
   PubMed Web of Science ®Google Scholar
• Kishii K, Chiba N, Morozumi M, et al. In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2010;54:3970–3973.
   PubMed Web of Science ®Google Scholar
• Miyazaki S, Hosoyama T, Furuya N, et al. In vitro and in vivo antibacterial activities of L-084, a novel oral carbapenem, against causative organisms of respiratory tract infections. Antimicrob Agents Chemother. 2001;45:203–207.
   PubMed Web of Science ®Google Scholar
• Kobayashi R, Konomi M, Hasegawa K, et al. In vitro activity of tebipenem, a new oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae. Antimicrob Agents Chemother. 2005;49:889–894.
   PubMed Web of Science ®Google Scholar
• Tajima T, Sato Y, Toyonaga Y, et al. Nationwide survey of the development of drug-resistant pathogens in the pediatric field in 2007 and 2010: drug sensitivity of Streptococcus pneumoniae in Japan (second report). J Infect Chemother. 2013;19:510–516.
   PubMed Web of Science ®Google Scholar
• Zhanel GG, Wiebe R, Dilay L, et al. Comparative review of the carbapenems. Drugs. 2007;67:1027–1052.
   PubMed Web of Science ®Google Scholar
• Yamada K, Sugano T, Baba N, et al. In vitro antimicrobial activity of tebipenem. Jpn J Chemother. 2009;57(S–1):1–14.
   Google Scholar
• Seenama C, Tiengrim S, Thamlikitkul V. In vitro activity of tebipenem against Burkholderia pseudomallei. Int J Antimicrob Agents. 2013;42:375.
   PubMed Web of Science ®Google Scholar
• Horita Y, Maeda S, Kazumi Y, et al. In vitro susceptibility of Mycobacterium tuberculosis isolates to an oral carbapenem alone or in combination with beta-lactamase inhibitors. Antimicrob Agents Chemother. 2014;58:7010–7014.
   PubMed Web of Science ®Google Scholar
• Kaushik A, Makkar N, Pandey P, et al. Carbapenems and rifampin exhibit synergy against Mycobacterium tuberculosis and Mycobacterium abscessus. Antimicrob Agents Chemother. 2015;59:6561–6567.
   PubMed Web of Science ®Google Scholar
• Mattoo R, Lloyd EP, Kaushik A, et al. LdtMav2, a nonclassical transpeptidase and susceptibility of Mycobacterium avium to carbapenems. Future Microbiol. 2017;12:595–607.
   PubMed Web of Science ®Google Scholar
• Fujisaki M, Sadamoto S, Ikedo M, et al. Development of interpretive criteria for tebipenem disk diffusion susceptibility testing with Staphylococcus spp. and Haemophilus influenzae. J Infect Chemother. 2011;17:17–23.
   PubMed Web of Science ®Google Scholar
• Itahashi K, Fukushima T, Nagura J, et al. Efficacy of tebipenem pivoxil (ME1211) on acute otitis media in chinchilla caused by penicillin-resistant Streptococcus pneumoniae (PRSP). 45th Intersci Conf Antimicrob Agents Chemother (ICAAC) 2005; Abstract B-738.
   Google Scholar
• Hotomi M, Suzumoto M, Itahashi K, et al. Efficacy of a novel oral carbapenem, tebipenem pivoxil (TBM-PI), against experimental otitis media caused by penicillin resistant Streptococcus pneumoniae in chinchilla. Vaccine. 2007;25:2478–2484.
   PubMed Web of Science ®Google Scholar
• Codjoe FS, Donkor ES. Carbapenem resistance: a review. Med Sci (Basel). 2017;6(1):E1.
   PubMedGoogle Scholar
• Adler M, Anjum M, Andersson DI, et al. Combinations of mutations in envZ, ftsI, mrdA, acrB and acrR can cause high-level carbapenem resistance in Escherichia coli. J Antimicrob Chemother. 2016;71:1188–1198.
   PubMed Web of Science ®Google Scholar
• Bassetti M, Nicolini L, Esposito S, et al. Current status of newer carbapenems. Curr Med Chem. 2009;16:564–575.
   PubMed Web of Science ®Google Scholar
• Iovleva A, Doi Y. Carbapenem-resistant Enterobacteriaceae. Clin Lab Med. 2017;37:303–315.
   PubMed Web of Science ®Google Scholar
• Nordmann P, Naas T, Poirel L. Global spread of carbapenemase-producing Enterobacteriaceae. Emerg Infect Dis. 2011;17:1791–1798.
   PubMed Web of Science ®Google Scholar
• Zilberberg MD, Nathanson BH, Sulham K, et al. Carbapenem resistance, inappropriate empiric treatment and outcomes among patients hospitalized with Enterobacteriaceae urinary tract infection, pneumonia and sepsis. BMC Infect Dis. 2017;17:279.
   PubMed Web of Science ®Google Scholar
• Mazzei T, Dentico P. The pharmacokinetics of oral cephalosporins. Clin Microbiol Infect. 2000;6(Suppl 3):53–54.
   PubMedGoogle Scholar
• Nakashima M, Morita J, Aizawa K. Pharamacokinetics and safety of tebipenem pivoxil fine granules, an oral carbapenem antibiotic, in healthy male volunteers. Jpn J Chemother. 2009;57(S–1):90–94.
   Google Scholar
• Isoda T, Ushirogochi H, Satoh K, et al. Syntheses and pharmacokinetic studies of prodrug esters for the development of oral carbapenem, L-084. J Antibiot (Tokyo). 2006;59:241–247.
   PubMed Web of Science ®Google Scholar
• Baba S, Yamanaka N, Suzuki K, et al. Clinical efficacy, safety and PK-PD analysis of tebipenem pivoxil in a phase II clinical trial in otolaryngological infections. Jpn J Antibiot. 2009;62:155–177.
   PubMedGoogle Scholar
• Kijima K, Sato N, Koresawa T, et al. Pharmacokinetics analysis of tebipenem pivoxil on a phase 2 clinical trial in otolaryngological infections. Jpn J Antibiot. 2009;154:143–154.
   Google Scholar
• Niki Y, Saito A, Watanabe N, et al. Tebipenem Pivoxil (ME1211), a Novel Oral Carbapenem, Showed High Bacterial and Clinical Effectiveness in a Phase II Clinical Trial on Community-Acquired Bacterial Pneumoniae (CAP). 47th Intersci Conf Antimicrob Agents Chemother (ICAAC) 2007; Abstract L-145.
   Google Scholar
• Sunakawa K. Pharmacological properties and clinical performance of the novel oral carbapenem antimicrobial drug, “Tebipenem pivoxil” (Orapenem® fine granules 10% for pediatric use). Jpn J Chemother. 2009;57:279–294.
   Google Scholar
• Yamanaka N, Furukawa M, Furuya, et al. Clinical efficacy of tebipenem pivoxil (ME1211), a novel oral carbapenem, in otolaryngological infections, a Phase II clinical trial (1). 45th Intersci Conf Antimicrob Agents Chemother (ICAAC) 2005; Abstract L-577.
   Google Scholar
• Iwata S, Ouchi K, Iwata N, et al. An open clinical study of tebipenem pivoxil in children with bacterial pneumonia. Jpn J Chemother. 2009;57(S–1):137–150.
   Google Scholar
• Suzuki K, Baba S, Totsuka K, et al. Double-blind comparative study of tebipenem pivoxil and high-dose cefditoren pivoxilin children with acute otitis media (Phase III). Jpn J Chemother. 2009;57(S–1):167–185.
   Google Scholar
• Sakata H, Kuroki H, Ouchi K, et al. World’s First Oral Carbapenem Study Group. Pediatric community-acquired pneumonia treated with a three-day course of tebipenem pivoxil. J Infect Chemother. 2017;23:307–311.
   PubMed Web of Science ®Google Scholar
• Liu CX, Kato N, Watanabe K, et al. Impact of a new quinolone, DU-6859a, and two oral carbapenems, CS-834 and L-084, on the rat and mouse caecal microflora. J Antimicrob Chemother. 2000;46:823–826.
   PubMed Web of Science ®Google Scholar
• Kataoka H, Kasahara H, Sasagawa Y, et al. Evaluation of safety and efficacy of tebipenem pivoxil granules for pediatric in pneumonia, otitis media, and sinusitis. Jpn J Antibiot. 2016;69:53–76.
   PubMedGoogle Scholar
• Bush K. Proliferation and significance of clinically relevant β-lactamases. Ann N Y Acad Sci. 2013;1277:84–90.
   PubMed Web of Science ®Google Scholar