tebipenem: an oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae; structure in first source
ID Source | ID |
---|---|
PubMed CID | 9800194 |
CHEMBL ID | 576981 |
SCHEMBL ID | 14769588 |
MeSH ID | M0484285 |
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 |
Tebipenem is an orally bioavailable carbapenem in development for the treatment of patients with complicated urinary tract infections.
Excerpt | Reference | Relevance |
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"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 |
Excerpt | Reference | Relevance |
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"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 |
Excerpt | Reference | Relevance |
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"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 |
Excerpt | Reference | Relevance |
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" 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 |
Excerpt | Reference | Relevance |
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"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 |
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.
Excerpt | Reference | Relevance |
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" 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 |
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.
Excerpt | Relevance | Reference |
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" 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 |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1311365 | Antibacterial activity against Enterococcus faecalis ATCC 19433 measured after 18 hrs by broth microdilution assay | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | An evolved oxazolidinone with selective potency against Mycobacterium tuberculosis and gram positive bacteria. |
AID521325 | Antimicrobial 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 method | 2008 | Antimicrobial 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. |
AID567480 | Bactericidal 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 serum | 2010 | Antimicrobial 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. |
AID567473 | Antimicrobial activity against gBLPAR-TEM1 Haemophilus influenzae by agar dilution method | 2010 | Antimicrobial 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. |
AID567470 | Antimicrobial activity against gBLNAS Haemophilus influenzae by agar dilution method | 2010 | Antimicrobial 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. |
AID567481 | Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 4 hrs by time-kill analysis | 2010 | Antimicrobial 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. |
AID567471 | Antimicrobial activity against gLow-BLNAR Haemophilus influenzae by agar dilution method | 2010 | Antimicrobial 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. |
AID521323 | Antimicrobial activity against rifampin-resistant Haemophilus influenzae Rd clone by broth dilution method | 2008 | Antimicrobial 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. |
AID567472 | Antimicrobial activity against gBLNAR Haemophilus influenzae by agar dilution method | 2010 | Antimicrobial 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. |
AID1871991 | Antimycobacterial activity against extensively drug-resistant Mycobacterium tuberculosis | 2022 | European journal of medicinal chemistry, Feb-05, Volume: 229 | Tuberculosis drug discovery: Progression and future interventions in the wake of emerging resistance. |
AID567476 | Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 4 hrs by time-kill analysis | 2010 | Antimicrobial 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. |
AID567485 | Bactericidal 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 serum | 2010 | Antimicrobial 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. |
AID567475 | Antimicrobial activity against gBLPACR-2 Haemophilus influenzae by agar dilution method | 2010 | Antimicrobial 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. |
AID567479 | Bactericidal 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 serum | 2010 | Antimicrobial 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. |
AID521324 | Antimicrobial activity against beta lactamase-nonproducing ampicillin-resistant Haemophilus influenzae MSC06647 isolate harboring Asn526Lys mutation in penicillin-binding protein 3 by broth dilution method | 2008 | Antimicrobial 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. |
AID1311377 | Antibacterial activity against Mycobacterium tuberculosis | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | An evolved oxazolidinone with selective potency against Mycobacterium tuberculosis and gram positive bacteria. |
AID1311364 | Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC 29213 measured after 18 hrs by broth microdilution assay | 2016 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15 | An evolved oxazolidinone with selective potency against Mycobacterium tuberculosis and gram positive bacteria. |
AID567474 | Antimicrobial activity against gBLPACR-1 Haemophilus influenzae by agar dilution method | 2010 | Antimicrobial 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. |
AID438297 | Inhibition of penicillin-sensitive Streptococcus pneumoniae R6 PBP2X preincubated for 1 hr before addition of substrate (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid | 2009 | Journal 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. |
AID567477 | Bactericidal activity against gBLNAR Haemophilus influenzae JPH002 assessed as reduction in bacterial load at MIC after 6 hrs by time-kill analysis | 2010 | Antimicrobial 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. |
AID772174 | Apparent permeability of the compound in pig LLC-PK1 cells | 2013 | ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8 | Design, synthesis, and evaluation of prodrugs of ertapenem. |
AID567483 | Bactericidal 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 serum | 2010 | Antimicrobial 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. |
AID567484 | Bactericidal 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 serum | 2010 | Antimicrobial 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. |
AID567482 | Bactericidal activity against gBLNAR Haemophilus influenzae JPH1306 assessed as reduction in bacterial load at MIC after 6 hrs by time-kill analysis | 2010 | Antimicrobial 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. |
AID438298 | Inhibition of penicillin-resistant Streptococcus pneumoniae 5204 PBP2X preincubated for 4 hrs before addition of substrate (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid | 2009 | Journal 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. |
AID567478 | Bactericidal 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 serum | 2010 | Antimicrobial 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 1 (1.41) | 18.2507 |
2000's | 15 (21.13) | 29.6817 |
2010's | 36 (50.70) | 24.3611 |
2020's | 19 (26.76) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (47.25) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 8 (11.11%) | 5.53% |
Reviews | 6 (8.33%) | 6.00% |
Case Studies | 1 (1.39%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 57 (79.17%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |