Page last updated: 2024-11-11

tebipenem

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Description

tebipenem: an oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9800194
CHEMBL ID576981
SCHEMBL ID14769588
MeSH IDM0484285

Synonyms (25)

Synonym
tebipenem
CHEMBL576981
ljc-11036
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, (4r,5s,6s)-
(1r,5s,6s)-6-(1(r)-hydroxyethyl)-1-methyl-2-(1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl)-1-carba-2-penem-3-carboxylic acid
q2twq1i31u ,
unii-q2twq1i31u
161715-21-5
tebipenem [who-dd]
tebipenem [mi]
CS-3444
SCHEMBL14769588
AC-35391
HY-A0076
DTXSID40167227
C21522
AKOS030526611
(4r,5s,6s)-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-carboxylic acid
AS-75271
(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-carboxylic acid
1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, [4r-[4a,5b,6b(r*)]]-
ljc 11036
Q27286930
(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-carboxylic acid
A899347

Research Excerpts

Overview

Tebipenem is an orally bioavailable carbapenem in development for the treatment of patients with complicated urinary tract infections.

ExcerptReferenceRelevance
"Tebipenem is an orally bioavailable carbapenem in development for the treatment of patients with complicated urinary tract infections. "( Evaluation of Oral Tebipenem as a Step-Down Therapy following Intravenous Ertapenem against Extended-Spectrum β-Lactamase-Producing Escherichia coli in a Hollow-Fiber
Ambrose, PG; Bhavnani, SM; Conde, H; Cotroneo, N; Friedrich, LV; Jones, S; VanScoy, BD, 2023
)
2.68

Actions

ExcerptReferenceRelevance
"Tebipenem displays a broad spectrum of activity against anaerobic, gram-positive, and gram-negative pathogens, including extended-spectrum β-lactamase producing Enterobacterales."( Tebipenem pivoxil hydrobromide-No PICC, no problem!
Cho, JC; Clark, M; Kronsberg, KA; Sodhi, V, 2021
)
2.79

Toxicity

ExcerptReferenceRelevance
"The incidence of adverse reactions related to symptoms and signs was 28."( [Clinical efficacy, safety and PK-PD analysis of tebipenem pivoxil in a phase II clinical trial in otolaryngological infections].
Baba, S; Furukawa, M; Furuya, N; Suzuki, K; Totsuka, K; Ubukata, K; Yamanaka, N, 2009
)
0.61

Pharmacokinetics

ExcerptReferenceRelevance
" We therefore performed an population pharmacokinetic analysis using plasma TBPM concentrations obtained from pediatric patients with otolaryngological infection or bacterial pneumonia (0."( Population pharmacokinetics of tebipenem pivoxil (ME1211), a novel oral carbapenem antibiotic, in pediatric patients with otolaryngological infection or pneumonia.
Hayashi, H; Kijima, K; Koresawa, T; Kurosawa, T; Mitomi, N; Morita, J; Sato, N; Shibasaki, S; Suzuki, H; Totsuka, K, 2008
)
0.63
" Cmax of TBPM in the non-fasting state was lowered to approximately 60% of that in the fasting state, however AUC(0-infinity) and urinary excretion of TBPM in the non-fasting state were almost equivalent to those in the fasting state when TBPM-PI fine granules were administered."( [Effect of diet on the pharmacokinetics of tebipenem pivoxil fine granules in healthy male volunteers].
Aizawa, K; Morita, J; Nakashima, M; Takata, T, 2009
)
0.62
" The primary pharmacokinetic parameters such as ka, kel, Vd/F and Tlag were estimated by the Bayesian method and then the secondary pharmacokinetic parameters such as tmax, Cmax, t1/2 and AUC were calculated."( [Pharmacokinetics analysis of tebipenem pivoxil in a phase II clinical trial in otolaryngological infections].
Hayashi, H; Kijima, K; Koresawa, T; Kurosawa, T; Morita, J; Sato, N; Shibasaki, S; Totsuka, K, 2009
)
0.64

Compound-Compound Interactions

ExcerptReferenceRelevance
"We evaluated the antituberculosis (anti-TB) activity of five β-lactams alone or in combination with β-lactamase inhibitors against 41 clinical isolates of Mycobacterium tuberculosis, including multidrug-resistant and extensively drug-resistant strains."( In vitro susceptibility of Mycobacterium tuberculosis isolates to an oral carbapenem alone or in combination with β-lactamase inhibitors.
Doi, N; Horita, Y; Kazumi, Y; Maeda, S, 2014
)
0.4

Bioavailability

Tebipenem is being developed as the first oral carbapenem for treatment of complicated urinary tract infections (cUTIs) in adults. Tebipenm pivoxil hydrobromide is a novel orally bioavailable prodrug that binds to penicillin-binding proteins.

ExcerptReferenceRelevance
" Tebipenem is the active form of tebipenem pivoxil, a novel oral carbapenem antibiotic that has a high level of bioavailability in humans, in addition to the above-mentioned features."( Crystal structures of biapenem and tebipenem complexed with penicillin-binding proteins 2X and 1A from Streptococcus pneumoniae.
Baba, N; Gomi, S; Ohsawa, F; Takeuchi, Y; Watanabe, T; Yamada, M, 2008
)
1.53
" In conclusion, the absorption rate of TBPM-PI was reduced in the non-fasting state after the administration of TBPM-PI fine granules, but intake of food had little influence on the absorption amount of TBPM."( [Effect of diet on the pharmacokinetics of tebipenem pivoxil fine granules in healthy male volunteers].
Aizawa, K; Morita, J; Nakashima, M; Takata, T, 2009
)
0.62
" (1) In mouse, rat, dog and monkey, TBPM-PI were absorbed quickly, and the bioavailability was (71."( [Pharmacokinetics of tebipenem pivoxil, a novel oral carbapenem antibiotic, in experimental animals].
Aoki, M; Hayashi, H; Kato, K; Kijima, K; Kurosawa, T; Morita, J; Shibasaki, S; Suzuki, K, 2009
)
0.67
" This agent is a prodrug to improve intestinal absorption of TBPM, an active form, and an absorption rate of TBPM-PI is higher than those of other prodrug-type β-lactam antibiotics."( Intestinal absorption mechanism of tebipenem pivoxil, a novel oral carbapenem: involvement of human OATP family in apical membrane transport.
Iguchi, M; Kato, K; Kikuchi, A; Kuraoka, E; Kurosawa, T; Shibasaki, S; Shirasaka, Y; Suzuki, H; Tamai, I, 2010
)
0.64
" SPR994 is a novel formulation of the orally bioavailable pivoxil prodrug of SPR859 (tebipenem) and is being developed as the first oral carbapenem for treatment of complicated urinary tract infections (cUTIs) in adults."( Characterization of SPR994, an Orally Available Carbapenem, with Activity Comparable to Intravenously Administered Carbapenems.
Jain, A; Pucci, MJ; Rubio, A, 2018
)
0.7
"Tebipenem pivoxil hydrobromide is a novel orally bioavailable prodrug of tebipenem, a carbapenem antimicrobial, that binds to penicillin-binding proteins, inhibiting the synthesis of the bacterial cell wall."( Tebipenem pivoxil hydrobromide-No PICC, no problem!
Cho, JC; Clark, M; Kronsberg, KA; Sodhi, V, 2021
)
3.51
" Tebipenem pivoxil hydrobromide is an orally bioavailable carbapenem with activity against uropathogenic Enterobacterales, including extended-spectrum beta-lactamase-producing and fluoroquinolone-resistant strains."( Oral Tebipenem Pivoxil Hydrobromide in Complicated Urinary Tract Infection.
Critchley, IA; Dane, A; Eckburg, PB; Jain, A; Keutzer, T; Kwak, H; Melnick, D; Moore, G; Muir, L; Phelan, AM; Talley, AK; Walpole, S, 2022
)
2.15
"Tebipenem pivoxil hydrobromide is an orally bioavailable carbapenem prodrug of the active agent tebipenem with broad-spectrum activity against drug-resistant Enterobacterales."( Relative bioavailability of crushed tebipenem administered through a nasogastric tube with and without enteral feeding.
Asempa, TE; Fouad, A; Nicolau, DP; Quintiliani, R, 2022
)
2.44
"Tebipenem is an orally bioavailable carbapenem in development for the treatment of patients with complicated urinary tract infections."( Evaluation of Oral Tebipenem as a Step-Down Therapy following Intravenous Ertapenem against Extended-Spectrum β-Lactamase-Producing Escherichia coli in a Hollow-Fiber
Ambrose, PG; Bhavnani, SM; Conde, H; Cotroneo, N; Friedrich, LV; Jones, S; VanScoy, BD, 2023
)
2.68

Dosage Studied

Tebipenem pivoxil hydrobromide is expected to have the potential to decrease the seizure threshold. It will likely require renal dosage adjustment for patients with altered renal function due to high renal clearance.

ExcerptRelevanceReference
" In order to treat these infections effectively, it is important to design optimal dosing regimens based on the pharmacokinetics/pharmacodynamics (PK/PD) relationships, which can be characterized by clarifying the pharmacokinetics of tebipenem (TBPM) in the pediatric population."( Population pharmacokinetics of tebipenem pivoxil (ME1211), a novel oral carbapenem antibiotic, in pediatric patients with otolaryngological infection or pneumonia.
Hayashi, H; Kijima, K; Koresawa, T; Kurosawa, T; Mitomi, N; Morita, J; Sato, N; Shibasaki, S; Suzuki, H; Totsuka, K, 2008
)
0.81
" The majority of dosage was excreted out of body by 48 hours after administration."( [Pharmacokinetics of tebipenem pivoxil, a novel oral carbapenem antibiotic, in experimental animals].
Aoki, M; Hayashi, H; Kato, K; Kijima, K; Kurosawa, T; Morita, J; Shibasaki, S; Suzuki, K, 2009
)
0.67
" Design and synthesis, in vitro and in vivo evaluation of diversified prodrugs of ertapenem, one of the only once daily dosed carbapenems is described."( Design, synthesis, and evaluation of prodrugs of ertapenem.
Bradley, P; Cama, L; Hafey, MJ; Ji, C; Meinke, PT; Nicoll-Griffith, DA; Olsen, DB; Rindgen, D; Singh, SB; Soll, R; Sun, W; Suzuki, T; Wang, L; Wang, N; Wu, H; Yu, H; Zhang, B, 2013
)
0.39
" As with other carbapenems, tebipenem pivoxil hydrobromide is expected to have the potential to decrease the seizure threshold and will likely require renal dosage adjustment for patients with altered renal function due to high renal clearance."( Tebipenem pivoxil hydrobromide-No PICC, no problem!
Cho, JC; Clark, M; Kronsberg, KA; Sodhi, V, 2021
)
2.36
" Using the 90% CI criteria, Cmaxand AUC0-8 values for tebipenem were found to be bioequivalent following alternative methods of administration compared with oral dosing of the whole tablet."( Relative bioavailability of crushed tebipenem administered through a nasogastric tube with and without enteral feeding.
Asempa, TE; Fouad, A; Nicolau, DP; Quintiliani, R, 2022
)
1.24
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1311365Antibacterial activity against Enterococcus faecalis ATCC 19433 measured after 18 hrs by broth microdilution assay2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
An evolved oxazolidinone with selective potency against Mycobacterium tuberculosis and gram positive bacteria.
AID521325Antimicrobial activity against beta lactamase-nonproducing ampicillin-resistant Haemophilus influenzae MSC06663 isolate harboring Met377Ile, Ser385Thr and Asn526Lys mutations in penicillin-binding protein 3 by broth dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
Comparison of the efficacies of oral beta-lactams in selection of Haemophilus influenzae transformants with mutated ftsI genes.
AID567480Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 6 hrs by time-kill analysis in presence of 10% human serum2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567473Antimicrobial activity against gBLPAR-TEM1 Haemophilus influenzae by agar dilution method2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567470Antimicrobial activity against gBLNAS Haemophilus influenzae by agar dilution method2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567481Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 4 hrs by time-kill analysis2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567471Antimicrobial activity against gLow-BLNAR Haemophilus influenzae by agar dilution method2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID521323Antimicrobial activity against rifampin-resistant Haemophilus influenzae Rd clone by broth dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
Comparison of the efficacies of oral beta-lactams in selection of Haemophilus influenzae transformants with mutated ftsI genes.
AID567472Antimicrobial activity against gBLNAR Haemophilus influenzae by agar dilution method2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID1871991Antimycobacterial activity against extensively drug-resistant Mycobacterium tuberculosis2022European journal of medicinal chemistry, Feb-05, Volume: 229Tuberculosis drug discovery: Progression and future interventions in the wake of emerging resistance.
AID567476Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 4 hrs by time-kill analysis2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567485Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 6 hrs by time-kill analysis in presence of 10% human serum2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567475Antimicrobial activity against gBLPACR-2 Haemophilus influenzae by agar dilution method2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567479Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 4 hrs by time-kill analysis in presence of 10% human serum2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID521324Antimicrobial activity against beta lactamase-nonproducing ampicillin-resistant Haemophilus influenzae MSC06647 isolate harboring Asn526Lys mutation in penicillin-binding protein 3 by broth dilution method2008Antimicrobial agents and chemotherapy, May, Volume: 52, Issue:5
Comparison of the efficacies of oral beta-lactams in selection of Haemophilus influenzae transformants with mutated ftsI genes.
AID1311377Antibacterial activity against Mycobacterium tuberculosis2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
An evolved oxazolidinone with selective potency against Mycobacterium tuberculosis and gram positive bacteria.
AID1311364Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 29213 measured after 18 hrs by broth microdilution assay2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
An evolved oxazolidinone with selective potency against Mycobacterium tuberculosis and gram positive bacteria.
AID567474Antimicrobial activity against gBLPACR-1 Haemophilus influenzae by agar dilution method2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID438297Inhibition of penicillin-sensitive Streptococcus pneumoniae R6 PBP2X preincubated for 1 hr before addition of substrate (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Discovery of new inhibitors of resistant Streptococcus pneumoniae penicillin binding protein (PBP) 2x by structure-based virtual screening.
AID567477Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 6 hrs by time-kill analysis2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID772174Apparent permeability of the compound in pig LLC-PK1 cells2013ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8
Design, synthesis, and evaluation of prodrugs of ertapenem.
AID567483Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 2 hrs by time-kill analysis in presence of 10% human serum2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567484Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 4 hrs by time-kill analysis in presence of 10% human serum2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID567482Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 6 hrs by time-kill analysis2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
AID438298Inhibition of penicillin-resistant Streptococcus pneumoniae 5204 PBP2X preincubated for 4 hrs before addition of substrate (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Discovery of new inhibitors of resistant Streptococcus pneumoniae penicillin binding protein (PBP) 2x by structure-based virtual screening.
AID567478Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 2 hrs by time-kill analysis in presence of 10% human serum2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
In vitro activity of tebipenem, a new oral carbapenem antibiotic, against beta-lactamase-nonproducing, ampicillin-resistant Haemophilus influenzae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (71)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (1.41)18.2507
2000's15 (21.13)29.6817
2010's36 (50.70)24.3611
2020's19 (26.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.25

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index47.25 (24.57)
Research Supply Index4.39 (2.92)
Research Growth Index5.96 (4.65)
Search Engine Demand Index68.99 (26.88)
Search Engine Supply Index1.98 (0.95)

This Compound (47.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (11.11%)5.53%
Reviews6 (8.33%)6.00%
Case Studies1 (1.39%)4.05%
Observational0 (0.00%)0.25%
Other57 (79.17%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]