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temocillin

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Description

temocillin: beta-lactam antibiotic with unusual spectrum of antibacterial activity & exceptional stability to bacterial beta-lactamases; RN given refers to di-Na salt (2S-(2alpha,5alpha,6alpha))-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

temocillin : A penicillin compound having a 6alpha-methoxy and 6beta-[2-carboxy(thiophen-3-yl)acetamido side-groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID171758
CHEMBL ID1276310
CHEBI ID51817
SCHEMBL ID34084
MeSH IDM0098594

Synonyms (49)

Synonym
brl-17421
temocillin (usan)
D06064
66148-78-5
einecs 266-184-1
temocillin
n-((2s,5r,6s)-2-carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-3-thiophenemalonamic acid
temocillinum [inn-latin]
temocillina [inn-spanish]
temocilline [inn-french]
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6alpha))-
(2s,5r,6s)-6-{[carboxy(thiophen-3-yl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
temocilline
temocillinum
CHEBI:51817 ,
(2s,5r,6s)-6-[2-carboxy(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6beta-[carboxy(thiophen-3-yl)acetamido]-6-methoxy-2,2-dimethylpenam-3alpha-carboxylic acid
temocillina
(2s,5r,6s)-6-{[carboxy(3-thienyl)acetyl]amino}-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2s,5r,6s)-6-[(3-hydroxy-3-oxo-2-thiophen-3-ylpropanoyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
brl 17421 [as sodium]
brl-17421 free acid
CHEMBL1276310
brl 17421 free acid
unii-03qb156w6i
temocillin [usan:inn:ban]
03qb156w6i ,
SCHEMBL34084
temocillin [who-dd]
temocillin [mart.]
temocillin [mi]
temocillin [inn]
n-[(2s,5r,6s)-2-carboxy-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]-3-thiophenemalonamic acid
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxy-3-thienylacetyl)amino)-6-methoxy-3,3-dimethyl-7-oxo-, (2s-(2.alpha.,5.alpha.,6.alpha.))-
temocillin [usan]
BVCKFLJARNKCSS-DWPRYXJFSA-N
DB12343
(2s,5r,6s)-6-(2-carboxy-2-(thiophen-3-yl)acetamido)-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2s,5r,6s)-6-[(2-carboxy-2-thiophen-3-ylacetyl)amino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
negaban
DTXSID201009398
Q3983108
gtpl10926
brl17421
CS-0356857
A900942
(2s,5r,6s)-6-[2-carboxy-2-(thiophen-3-yl)acetamido]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
EN300-19766369
HY-145158

Research Excerpts

Overview

Temocillin is an old 'revived' antibiotic that may play an important role in the treatment of febrile urinary tract infection (UTI) It is a 6-α-methox derivative of ticarcillin that is resilient to ESBLs.

ExcerptReferenceRelevance
"Temocillin is a useful alternative to other broad-spectrum anti-Gram-negative agents currently utilised in the OPAT setting and supports the wider antimicrobial stewardship agenda."( Evaluation of the stability of temocillin in elastomeric infusion devices used for outpatient parenteral antimicrobial therapy in accordance with the requirements of the UK NHS Yellow Cover Document.
Drummond, F; Gilchrist, M; Hills, T; Jamieson, C; Roberts, J; Santillo, M; Seaton, RA; Sime, FB; Wallis, S, 2023
)
1.92
"Temocillin is an interesting alternative to carbapenems for susceptible Enterobacteriaceae. "( Stability of temocillin in outpatient parenteral antimicrobial therapy: is it a real option?
De Alarcón, A; Fernández-Polo, A; Fernández-Rubio, B; Gil-Navarro, MV; Gutiérrez-Urbón, JM; Gutiérrez-Valencia, A; Herrera-Hidalgo, L; López-Cortés, LE; Luque-Márquez, R; Luque-Pardos, S; Rodríguez-Baño, J, 2023
)
2.72
"Temocillin is a carboxypenicillin antibiotic indicated in complicated urinary tract infections due to susceptible ESBL-producing Enterobacteriaceae. "( Temocillin dosage adjustment in a preterm infant with severe renal disease: a case report.
Brenkman, M; Charmillon, A; Dumangin, G; Gambier, N; Kolodziej, A; Pape, E; Scala-Bertola, J; Vrillon, I, 2020
)
3.44
"Temocillin is an alternative to treat urinary tract infections with bacteria producing extended spectrum beta-lactamase (ESBL). "( [Temocillin and urinary tract infections].
Brureau, L; Bruyère, F; Roblot, F; Vallée, M, 2017
)
2.81
"Temocillin is an old 'revived' antibiotic that may play an important role in the treatment of febrile urinary tract infection (UTI). "( Temocillin against Enterobacteriaceae isolates from community-acquired urinary tract infections: low rate of resistance and good accuracy of routine susceptibility testing methods.
Alexandre, K; Caron, F; Dahyot, S; Delbos, V; Etienne, M; Fabre, R; Pestel-Caron, M; Réveillon-Istin, M, 2018
)
3.37
"Temocillin is a 6α-methoxy derivative of ticarcillin that is resilient to ESBLs. "( Activity of temocillin in a murine model of urinary tract infection due to Escherichia coli producing or not producing the ESBL CTX-M-15.
Chau, F; Couffignal, C; Fantin, B; Lepeule, R; Massias, L; Mentre, F; Rossi, B; Ruppé, E; Soubirou, JF, 2015
)
2.24
"Temocillin is a β-lactam antibiotic with a long half-live and enhanced activity against most Gram-negative bacteria, including extended-spectrum β-lactamase-producers, thus making it an ideal candidate for use in this setting."( Thrice-weekly temocillin administered after each dialysis session is appropriate for the treatment of serious Gram-negative infections in haemodialysis patients.
Capron, A; Miranda Bastos, AC; Spinewine, A; Tulkens, PM; Van Bambeke, F; Vandecasteele, SJ, 2015
)
1.5
"Temocillin is a 6-α-methoxy derivative of ticarcillin that shows in vitro activity against Enterobacteriaceae producing Klebsiella pneumoniae carbapenemase (KPC). "( Activity of temocillin in a lethal murine model of infection of intra-abdominal origin due to KPC-producing Escherichia coli.
Alexandre, K; Cattoir, V; Chau, F; Fantin, B; Guérin, F; Lefort, A; Massias, L, 2016
)
2.26
"Temocillin is a semi-synthetic 6-alpha-methoxy derivative of ticarcillin. "( In vitro activity of temocillin against extended spectrum beta-lactamase-producing Escherichia coli.
de Mendonça, R; Frankard, J; Malaviolle, V; Nonhoff, C; Rodriguez-Villalobos, H; Struelens, MJ, 2006
)
2.1
"Temocillin is a narrow spectrum penicillin with high stability to most beta-lactamases including AmpC types and extended-spectrum types (ESBLs). "( In vitro activity of temocillin against prevalent extended-spectrum beta-lactamases producing Enterobacteriaceae from Belgian intensive care units.
Berhin, C; Claeys, G; Delmée, M; Glupczynski, Y; Huang, TD; Ide, L; Ieven, G; Pierard, D; Rodriguez-Villalobos, H; Struelens, M; Vaneldere, J, 2007
)
2.1
"Temocillin is a carboxypenicillin; a methoxy group in the 6-alpha position should confer to the molecule greater stability to beta-lactamases. "( [In vitro study of the bacteriostatic and bactericidal activity of temocillin (BRL 17421)].
Chanal, M; Cluzel, M; Glanddier, Y; Joly, B; Sirot, J, 1983
)
1.94
"Temocillin is a 6 alpha-methoxy penicillin which shows poor affinity for the penicillin-binding proteins (PBPs) of Escherichia coli K-12 when tested by competition with [14C]penicillin G or [125I]penicillin X. "( Affinity of temocillin for Escherichia coli K-12 penicillin-binding proteins.
Baron, P; Cole, M; Hill, G; Labia, R; Masson, JM, 1984
)
2.09
"Temocillin is a new penicillin combining activity against Gram-positive organisms, beta-lactamase stability and an exceptionally long half-life. "( Temocillin elimination in patients with varying degrees of renal failure.
Price, JD; Wise, R; Wright, N, 1983
)
3.15
"Temocillin is a beta-lactamase-stable penicillin with a selective. "( Temocillin in the treatment of pyelonephritis in children.
Lauwers, S; Pintens, H; Verboven, M, 1987
)
3.16
"Temocillin is a recently developed penicillin with a methoxy group in the 6-alpha position. "( Temocillin. In vitro activity compared with other antibiotics.
Bouza, E; Gomez-Alferez, A; Loza, E; Martinez-Beltran, J; Romero-Vivas, J, 1985
)
3.15
"Temocillin is a novel injectable beta-lactam antibiotic designed for parenteral use. "( Temocillin. Summary of safety studies.
Cockburn, A; Jackson, D; Mellows, G; White, DJ, 1985
)
3.15
"Temocillin is a new semisynthetic beta-lactam antibiotic with a spectrum of activity against most aerobic Gram-negative bacteria. "( Biliary concentrations of temocillin.
Greengrass, A; Moryson, CJ; Poston, GJ, 1985
)
2.01

Effects

Temocillin has been shown to be a good option for phenotypic screening. It is hydrolysed by the OXA-48-group enzymes, whereas ESBLs, AmpC and some other carbapenemases have a lower hydrolytic effect.

ExcerptReferenceRelevance
"Temocillin has a strong bactericidal effect, along with high tolerability and a good safety profile."( Budget impact analysis of temocillin insurance coverage for urinary tract infections caused by ESBL-producing pathogens in Iran.
Ghasemi, H; Sabouri, M; Seyedifar, M; Soodi, O, 2023
)
1.93
"Temocillin has a strong bactericidal effect, along with high tolerability and a good safety profile."( Budget impact analysis of temocillin insurance coverage for urinary tract infections caused by ESBL-producing pathogens in Iran.
Ghasemi, H; Sabouri, M; Seyedifar, M; Soodi, O, 2023
)
1.93
"Temocillin has been shown to be a good option for phenotypic screening as it is hydrolysed by the OXA-48-group enzymes, whereas ESBLs, AmpC and some other carbapenemases have a lower hydrolytic effect on this antimicrobial."( Evaluation of temocillin for phenotypic carbapenemase screening of Escherichia coli and Salmonella enterica isolates in relation to the presence of genes encoding ESBLs and carbapenemase production.
Cavaco, LM; Hammerum, AM; Hansen, F; Hasman, H; Hendriksen, RS; Hill, RLR; Le Hello, S; Mushtaq, S; Woodford, N, 2019
)
1.6
"Temocillin has pronounced in vitro activity against both penicillin-sensitive and penicillinase-producing gonococci. "( Single dose therapy with temocillin in acute gonorrhoea.
Hulla, FW; Kammacher, D; Milbradt, R; Reimer, G, 1985
)
2.02

Pharmacokinetics

Temocillin appears to be a penicillin with a prolonged half-life and high AUC. Pharmacokinetic parameters of temocillin were similar both for the three iv doses and for the im dose.

ExcerptReferenceRelevance
" The values of the pharmacokinetic parameters were as follows: AUC 509."( Pharmacokinetics of temocillin after intravenous and intramuscular administration.
Dvorácek, K; Janků, I; Krebs, V; Modr, Z; Morávek, J; Sechser, T, 1986
)
0.59
" The R-epimer was twice as rapidly cleared, had a 23% larger volume of distribution and a 60% shorter beta half-life than the S-epimer."( Human pharmacokinetics of temocillin (BRL 17421) side chain epimers.
Guest, EA; Horton, R; Mellows, G; Slocombe, B; Swaisland, AJ; Tasker, TC, 1985
)
0.57
"7-fold increase in the beta half-life and the area under the curve (AUC), respectively."( Effect of renal function and dialysis on temocillin pharmacokinetics.
Boelaert, J; Daneels, R; Lambert, AM; Mellows, G; Schurgers, M; Swaisland, AJ; Van Landuyt, HW, 1985
)
0.54
" The R epimer had a 2-fold greater total plasma clearance, a 23% larger volume of distribution and a shorter beta half-life than the S epimer."( Human pharmacokinetics and antimicrobial activities of the temocillin epimers.
Guest, EA; Horton, R; Mellows, G; Slocombe, B; Swaisland, AJ; Tasker, TC; White, AR, 1985
)
0.51
" Thus, temocillin appears to be a penicillin with a prolonged half-life and high AUC."( Pharmacokinetics of temocillin in volunteers.
Feike, M; Hampel, B; Koeppe, P; Lode, H, 1985
)
1.05
" Pharmacokinetic parameters of temocillin were similar both for the three iv doses and for the im dose."( Pharmacokinetics of temocillin (BRL 17421) in subjects with normal and impaired renal function.
Borsa, F; Fillastre, JP; Godin, M; Humbert, G; Leroy, A, 1983
)
0.88
"(i) In vitro evaluation of temocillin stability and compatibility with other drugs under conditions pertinent of CI in IC patients; (ii) pharmacokinetic study in patients treated by CI (4 g/day; n = 6) versus [twice daily (2 g every 12 h); n = 6]; (iii) population pharmacokinetic analysis of twice daily with Monte Carlo simulations to determine 95% probability of target attainment (PTA(95)) versus MIC (based on time above MIC > or = 40% for measured free drug)."( Continuous versus intermittent infusion of temocillin, a directed spectrum penicillin for intensive care patients with nosocomial pneumonia: stability, compatibility, population pharmacokinetic studies and breakpoint selection.
Basma, V; Carryn, S; De Jongh, R; Hens, R; Mouton, JW; Tulkens, PM, 2008
)
0.91
" With twice daily, Cmax (total drug) was 147 +/- 12."( Continuous versus intermittent infusion of temocillin, a directed spectrum penicillin for intensive care patients with nosocomial pneumonia: stability, compatibility, population pharmacokinetic studies and breakpoint selection.
Basma, V; Carryn, S; De Jongh, R; Hens, R; Mouton, JW; Tulkens, PM, 2008
)
0.61
" After intravenous infusion, temocillin showed a prolonged elimination half-life of approximately 5 h."( Pharmacokinetics and Pharmacodynamics of Temocillin.
Alexandre, K; Fantin, B, 2018
)
1.04
" However, some aspects of the pharmacokinetic (PK) profile of the drug are still to be elucidated: subcutaneous administration of temocillin might be of interest as an alternative to the intravenous route in selected patients."( Single-dose pharmacokinetics of temocillin in plasma and soft tissues of healthy volunteers after intravenous and subcutaneous administration: a randomized crossover microdialysis trial.
Capron, A; Duchek, M; Lackner, E; Matzneller, P; Mouton, JW; Ngougni Pokem, P; Nussbaumer-Pröll, A; Österreicher, Z; Van Bambeke, F; Van de Velde, S; Wallemacq, PE; Wulkersdorfer, B; Zeitlinger, M, 2020
)
1.05

Compound-Compound Interactions

Mice were treated for 24 h with fosfomycin alone or in combination with temocillin. Amoxycillin, clavulanic acid and ticarcillin displaced bilirubin at concentrations higher than those found clinically.

ExcerptReferenceRelevance
" Amoxycillin, clavulanic acid in combination with either amoxycillin or ticarcillin, temocillin and cloxacillin displaced bilirubin at concentrations much higher than those found clinically."( Displacement of bilirubin from cord serum by sulphadimethoxine, amoxycillin, clavulanic acid in combination with either amoxycillin or ticarcillin, temocillin and cloxacillin.
Davies, BE, 1985
)
0.69
" The combination beta-lactam-ciprofloxacin-tobramycin was the combination with the most consistently synergistic effect."( Comparative in vitro activities of meropenem, imipenem, temocillin, piperacillin, and ceftazidime in combination with tobramycin, rifampin, or ciprofloxacin against Burkholderia cepacia isolates from patients with cystic fibrosis.
Bingen, E; Bonacorsi, S; Fitoussi, F; Lhopital, S, 1999
)
0.55
" Mice were treated for 24 h with fosfomycin alone or in combination with temocillin."( Activity of fosfomycin alone or combined with temocillin in vitro and in a murine model of peritonitis due to KPC-3- or OXA-48-producing Escherichia coli.
Berleur, M; Cattoir, V; Chau, F; de Lastours, V; Fantin, B; Guérin, F; Massias, L; Poujade, J, 2018
)
0.97

Bioavailability

ExcerptReferenceRelevance
"BRL 20330 is the o-methyl phenyl ester of temocillin which is well absorbed after oral administration and converted to temocillin in the body."( BRL 20330, an oral prodrug of temocillin: bioavailability studies in man.
Basker, MJ; Merrikin, DJ; Ponsford, RJ; Slocombe, B; Tasker, TC, 1986
)
0.82
" BRL 17421 was poorly absorbed after oral administration."( BRL 17421, a novel beta-lactam antibiotic, highly resistant to beta-lactamases, giving high and prolonged serum levels in humans.
Basker, MJ; Bentley, PH; Clayton, JP; Cole, M; Comber, KR; Dixon, RA; Edmondson, RA; Jackson, D; Merrikin, DJ; Slocombe, B; Sutherland, R, 1981
)
0.26

Dosage Studied

Temocillin dosing adjustment performed in the present reported case allowed safe and effective treatment. Considering <5% degradation, the current data supports twice daily dosing of temocillin within the OPAT setting. Temocillin dosage adjustments in renal failure are proposed.

ExcerptRelevanceReference
"An in-vitro kinetic model was used to demonstrate the bactericidal activity of concentrations of temocillin achieved in extravascular body fluids following a 1 g intravenous dosage in man."( Activity of human extravascular temocillin concentrations simulated in an in-vitro kinetic model against beta-lactamase producing gram-negative bacilli.
Cooper, CE; Slocombe, B; White, AR, 1991
)
0.78
" Based on available temocillin pharmacokinetics and recommended dosage schedules, the minimum inhibitory concentration breakpoints chosen were: greater than or equal to 32 micrograms/ml = resistant and less than or equal to 16 micrograms/ml = susceptible."( Interpretive criteria for temocillin disk diffusion susceptibility testing.
Barry, AL; Fuchs, PC; Jones, RN; Thornsberry, C, 1985
)
0.89
" Over an 8-hour period, the serum and blister fluid concentrations exceeded the MIC90 of susceptible bacteria by 2-fold or greater, suggesting that twice or even once daily dosing with temocillin may be sufficient."( Pharmacokinetics and tissue penetration of temocillin.
Brown, RM; Lockley, MR; Wise, R, 1985
)
0.72
" Temocillin dosage adjustments in renal failure are proposed."( Effect of renal function and dialysis on temocillin pharmacokinetics.
Boelaert, J; Daneels, R; Lambert, AM; Mellows, G; Schurgers, M; Swaisland, AJ; Van Landuyt, HW, 1985
)
1.45
" Dose-reduction factors were derived which allowed the determination of the dosing regimen necessary to achieve approximately the same high plasma concentrations (and the same AUCs) in patients with impaired renal function as in healthy subjects."( Temocillin pharmacokinetics in normal and impaired renal function.
Höffler, D; Koeppe, P, 1985
)
1.71
"Temocillin was given to 33 patients with urinary tract infection as a once daily dosage regimen of 500mg intramuscularly or Ig intravenously for 7 to 10 days."( The treatment of complicated and uncomplicated urinary tract infections with temocillin.
Kosmidis, J, 1985
)
1.94
"Temocillin, a new beta-lactamase-stable penicillin, was administered in a dosage of 2g twice daily to 25 biliary surgery patients in whom potential septic complications were a concern."( Therapeutic results and tissue concentrations of temocillin in surgical patients.
Adam, D; Klein, HE; Wittke, RR, 1985
)
1.97
" This relationship has been used to suggest dosage schedules for temocillin in patients with renal insufficiency."( The pharmacokinetics of temocillin in patients with normal and impaired renal function.
Boelaert, J; Daneels, R; Lambert, AM; Mellows, G; Schurgers, M; Swaisland, AJ; Van Landuyt, HW; Wolf, J, 1983
)
0.81
" It is suggested that unlike other penicillins this compound may give adequate antibacterial concentration with once daily dosing in subjects with normal renal function; this will certainly require reduction in subjects with severely impaired renal function."( Temocillin elimination in patients with varying degrees of renal failure.
Price, JD; Wise, R; Wright, N, 1983
)
1.71
" Pharmacokinetic/pharmacodynamic analysis, aided by Monte-Carlo simulations, suggests a breakpoint of 8 mg/L for the registered maximum dosage of 4 g daily."( Temocillin revived.
Livermore, DM; Tulkens, PM, 2009
)
1.8
" Aims To assess temocillin clinical and microbiological cure rates (CCR and MCR) in infection caused by ESBL/dAmpC-producing Enterobacteriaceae and the effects of different dosage regimens."( Temocillin use in England: clinical and microbiological efficacies in infections caused by extended-spectrum and/or derepressed AmpC β-lactamase-producing Enterobacteriaceae.
Aali, A; Awad-El-Kariem, FM; Balakrishnan, I; Brudney, D; Carryn, S; Ghazy, A; Iyer, S; Khan, I; Kumari, P; Ladenheim, D; Mulla, R; Tan, B; Van de Velde, S; Virgincar, N, 2011
)
2.16
" Significantly higher CCR and MCR occurred in patients treated with temocillin at optimal dosage [2 g twice daily or renally adjusted equivalent (ORAE)] compared with those treated with a suboptimal dosage (<2 g twice daily ORAE) (CCR 91% and MCR 92% versus CCR 73% and MCR 63%)."( Temocillin use in England: clinical and microbiological efficacies in infections caused by extended-spectrum and/or derepressed AmpC β-lactamase-producing Enterobacteriaceae.
Aali, A; Awad-El-Kariem, FM; Balakrishnan, I; Brudney, D; Carryn, S; Ghazy, A; Iyer, S; Khan, I; Kumari, P; Ladenheim, D; Mulla, R; Tan, B; Van de Velde, S; Virgincar, N, 2011
)
2.05
" Mean, median and range of percentages of the dosing interval during which the free drug concentration remained >16 mg/L were 76."( Temocillin (6 g daily) in critically ill patients: continuous infusion versus three times daily administration.
Carryn, S; Dugernier, T; Laterre, PF; Mouton, JW; Muller, AE; Tulkens, PM; Van de Velde, S; Wittebole, X, 2015
)
1.86
" The free temocillin concentration remained >16 mg/L (MIC90 threshold for most Enterobacteriaceae) during 48%, 67% and 71% of the dosing interval for patients receiving 1 g q24h, 2 g q48h and 3 g q72h, respectively, suggesting appropriate exposure for the two latter therapeutic schemes."( Thrice-weekly temocillin administered after each dialysis session is appropriate for the treatment of serious Gram-negative infections in haemodialysis patients.
Capron, A; Miranda Bastos, AC; Spinewine, A; Tulkens, PM; Van Bambeke, F; Vandecasteele, SJ, 2015
)
1.18
" Data regarding actual wild-type MIC distribution, clinical efficacy, PK profiling in volunteers or patients, and PD targets are scarce, and further studies are required to support appropriate dosing recommendations and determination of clinical breakpoints."( Pharmacokinetics and Pharmacodynamics of Temocillin.
Alexandre, K; Fantin, B, 2018
)
0.75
" The dosage recommended is currently, in the normo-renal patient, 4g per day by intermittent infusion or continuously after a loading dose of 2g."( [Temocillin and urinary tract infections].
Brureau, L; Bruyère, F; Roblot, F; Vallée, M, 2017
)
1.37
"To develop a population model describing temocillin pharmacokinetics (PK) in patients undergoing haemodialysis and investigate how pharmacokinetic/pharmacodynamic (PD) targets can be met with different dosage regimens."( Temocillin dosing in haemodialysis patients based on population pharmacokinetics of total and unbound concentrations and Monte Carlo simulations.
Miranda Bastos, AC; Spinewine, A; Tulkens, PM; Van Bambeke, F; Vandecasteele, SJ, 2018
)
2.19
"Sixteen patients received the currently licenced dosing of 1, 2 or 3 g of temocillin (total of 61 doses) corresponding to an inter-dialytic period of 20, 44 or 68 h, respectively, and a dialysis period of 4 h."( Temocillin dosing in haemodialysis patients based on population pharmacokinetics of total and unbound concentrations and Monte Carlo simulations.
Miranda Bastos, AC; Spinewine, A; Tulkens, PM; Van Bambeke, F; Vandecasteele, SJ, 2018
)
2.15
" The currently licenced dosing achieved a 90% PTA for an MIC up to 8 mg/L."( Temocillin dosing in haemodialysis patients based on population pharmacokinetics of total and unbound concentrations and Monte Carlo simulations.
Miranda Bastos, AC; Spinewine, A; Tulkens, PM; Van Bambeke, F; Vandecasteele, SJ, 2018
)
1.92
"Currently licensed dosage regimen is suboptimal for MICs >8 mg/L (frequently found in clinical isolates)."( Temocillin dosing in haemodialysis patients based on population pharmacokinetics of total and unbound concentrations and Monte Carlo simulations.
Miranda Bastos, AC; Spinewine, A; Tulkens, PM; Van Bambeke, F; Vandecasteele, SJ, 2018
)
1.92
"To investigate the feasibility and plasma PK of subcutaneous dosing as well as soft tissue PK of temocillin after intravenous administration to healthy volunteers."( Single-dose pharmacokinetics of temocillin in plasma and soft tissues of healthy volunteers after intravenous and subcutaneous administration: a randomized crossover microdialysis trial.
Capron, A; Duchek, M; Lackner, E; Matzneller, P; Mouton, JW; Ngougni Pokem, P; Nussbaumer-Pröll, A; Österreicher, Z; Van Bambeke, F; Van de Velde, S; Wallemacq, PE; Wulkersdorfer, B; Zeitlinger, M, 2020
)
1.06
"Subcutaneous dosing caused some infusion site discomfort but resulted in sustained drug concentrations over time with only slightly decreased overall exposure compared with intravenous dosing."( Single-dose pharmacokinetics of temocillin in plasma and soft tissues of healthy volunteers after intravenous and subcutaneous administration: a randomized crossover microdialysis trial.
Capron, A; Duchek, M; Lackner, E; Matzneller, P; Mouton, JW; Ngougni Pokem, P; Nussbaumer-Pröll, A; Österreicher, Z; Van Bambeke, F; Van de Velde, S; Wallemacq, PE; Wulkersdorfer, B; Zeitlinger, M, 2020
)
0.84
"Temocillin dosing adjustment performed in the present reported case allowed safe and effective treatment."( Temocillin dosage adjustment in a preterm infant with severe renal disease: a case report.
Brenkman, M; Charmillon, A; Dumangin, G; Gambier, N; Kolodziej, A; Pape, E; Scala-Bertola, J; Vrillon, I, 2020
)
3.44
" Considering <5% degradation, the current data supports twice daily dosing of temocillin within the OPAT setting."( Evaluation of the stability of temocillin in elastomeric infusion devices used for outpatient parenteral antimicrobial therapy in accordance with the requirements of the UK NHS Yellow Cover Document.
Drummond, F; Gilchrist, M; Hills, T; Jamieson, C; Roberts, J; Santillo, M; Seaton, RA; Sime, FB; Wallis, S, 2023
)
1.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
penicillinAny member of the group of substituted penams containing two methyl substituents at position 2, a carboxylate substituent at position 3 and a carboxamido group at position 6.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID529577Ratio of Kcat to Km for Pseudomonas maltophilia ULA-511 beta-Lactamase L-12008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID562334Antimicrobial activity against Escherichia coli DH5alpha harboring plasmid pBC-SK after 18 hrs by broth microdilution method2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
IND-6, a highly divergent IND-type metallo-beta-lactamase from Chryseobacterium indologenes strain 597 isolated in Burkina Faso.
AID587732Activity of Pseudomonas aeruginosa strain PS 297 metallo-beta-lactamase IMP-1 expressed in Escherichia coli BL21(DE3) assessed as substrate hydrolysis using 100 uM nitrocefin2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID529575Activity of Erwinia carotovora subsp. atroseptica DSM 30184 beta-lactamase CAR-12008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID529576Ratio of Kcat to Km for Erwinia carotovora subsp. atroseptica DSM 30184 beta-Lactamase CAR-12008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID587731Ratio of Kcat to Km for Pseudomonas aeruginosa strain PS 297 metallo-beta-lactamase IMP18 expressed in Escherichia coli BL21(DE3) assessed as substrate hydrolysis using 100 uM nitrocefin2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID559103Antimicrobial activity against Escherichia coli DH10B by agar dilution method2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID559100Antimicrobial activity against Klebsiella pneumoniae expressing beta-lactamase KPC gene by agar dilution method2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID587728Antimicrobial activity against Escherichia coli DH5alpha carrying Pseudomonas aeruginosa strain PS 297 IMP-1-pLBII after 18 hrs by microdilution broth method2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID529572Antimicrobial activity against Erwinia carotovora subsp. atroseptica DSM 30184 after 24 hrs by broth microdilution method2008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID559102Antimicrobial activity against Escherichia coli DH10B harboring pBCSK plasmid expressing beta-lactamase KPC gene by agar dilution method2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID587729Antimicrobial activity against Escherichia coli DH5alpha carrying empty pBC-SK after 18 hrs by microdilution broth method2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID529574Antimicrobial activity against Escherichia coli DH5alpha harboring plasmid BC-SK after 24 hrs by broth microdilution method2008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID559107Drug level in human urine at 500 mg, im bid for 3 days2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID587730Activity of Pseudomonas aeruginosa strain PS 297 metallo-beta-lactamase IMP-18 expressed in Escherichia coli BL21(DE3) assessed as substrate hydrolysis using 100 uM nitrocefin2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID559104Cmax in human serum at 1 gram, iv2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID529582Ratio of Kcat to Km for Bradyrhizobium japonicum beta-Lactamase BJP-12008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID587727Antimicrobial activity against Escherichia coli DH5alpha carrying Pseudomonas aeruginosa strain PS 297 IMP-18-pLBII after 18 hrs by microdilution broth method2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID559101Antimicrobial activity against Escherichia coli clinical isolates expressing beta-lactamase KPC gene by agar dilution method2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID562331Antimicrobial activity against Escherichia coli DH5alpha harboring metallo-beta-lactamase IND-6 after 18 hrs by broth microdilution method2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
IND-6, a highly divergent IND-type metallo-beta-lactamase from Chryseobacterium indologenes strain 597 isolated in Burkina Faso.
AID559105Protein binding in human serum at 1 gram, iv2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID559106Half life in human serum at 1 gram, iv2009Antimicrobial agents and chemotherapy, Jun, Volume: 53, Issue:6
Activity of temocillin against KPC-producing Klebsiella pneumoniae and Escherichia coli.
AID529573Antimicrobial activity against Escherichia coli DH5alpha harboring plasmid pLBII carrying beta-lactamase CAR-1 gene after 24 hrs by broth microdilution method2008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID587733Ratio of Kcat to Km for Pseudomonas aeruginosa strain PS 297 metallo-beta-lactamase IMP-1 expressed in Escherichia coli BL21(DE3) assessed as substrate hydrolysis using 100 uM nitrocefin2011Antimicrobial agents and chemotherapy, Jan, Volume: 55, Issue:1
Genetic context and biochemical characterization of the IMP-18 metallo-beta-lactamase identified in a Pseudomonas aeruginosa isolate from the United States.
AID529579Ratio of Kcat to Km for Legionella gormanii ATCC 33297T beta-Lactamase FEZ-12008Antimicrobial agents and chemotherapy, Jul, Volume: 52, Issue:7
Functional diversity among metallo-beta-lactamases: characterization of the CAR-1 enzyme of Erwinia carotovora.
AID562328Antimicrobial activity against Chryseobacterium indologenes 597 expressing metallo-beta-lactamase IND-6 after 18 hrs by broth microdilution method2009Antimicrobial agents and chemotherapy, Oct, Volume: 53, Issue:10
IND-6, a highly divergent IND-type metallo-beta-lactamase from Chryseobacterium indologenes strain 597 isolated in Burkina Faso.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (212)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990105 (49.53)18.7374
1990's9 (4.25)18.2507
2000's17 (8.02)29.6817
2010's55 (25.94)24.3611
2020's26 (12.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 49.76

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 Index49.76 (24.57)
Research Supply Index5.46 (2.92)
Research Growth Index5.02 (4.65)
Search Engine Demand Index78.39 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (49.76)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials17 (7.87%)5.53%
Reviews9 (4.17%)6.00%
Case Studies9 (4.17%)4.05%
Observational0 (0.00%)0.25%
Other181 (83.80%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (11)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Randomised Controlled Trial of Temocillin vs Meropenem for the Targeted Treatment of Bacteraemia Due to Enterobacteriaceae Showing Resistance to Third Generation Cephalosporins [NCT04478721]Phase 3334 participants (Anticipated)Interventional2020-12-15Recruiting
Practical Use of Temocillin in Enterobacteriaceae Resistant to Third Generation of Cephalosporins: Experience of Two French University Hospitals [NCT05413772]29 participants (Actual)Observational2022-10-20Completed
Population Pharmacokinetics and Pharmacodynamics of Beta-lactams of Interest in Adult Patients From Intensive Care Units [NCT03440216]20 participants (Anticipated)Interventional2018-03-15Recruiting
Plasma Protein Binding and Population Pharmacokinetics and Pharmacodynamics of Total and Unbound Temocillin in Patients With Complicated Urinary Tract Infection or Pyelonephritis, Lower Respiratory Tract Infection, or Abdominal Infection. [NCT03557840]60 participants (Anticipated)Interventional2019-04-01Recruiting
Temocillin Pharmacokinetics in Paediatrics [NCT02260102]Phase 445 participants (Anticipated)Interventional2016-02-17Recruiting
Temocillin Versus a Carbapenem as Initial Intravenous Treatment for Extended-spectrum Beta-lactamase Related Urinary Tract Infections, a Non-inferiority Study [NCT03543436]Phase 329 participants (Actual)Interventional2019-01-04Completed
Efficacy of Temocillin in Urinary Tract Infection Due to ESBL Producing and AmpC Hyperproducing Enterobacteriaceae [NCT02681263]Phase 425 participants (Actual)Interventional2016-04-30Active, not recruiting
A Randomized, Controlled, Multicentre Trial of Collateral Damage on the Intestinal Microbiota Inferred by Temocillin Versus Cefotaxime in Patients Receiving Empirical Treatment for Febrile Urinary Tract Infections [NCT02959957]Phase 4157 participants (Actual)Interventional2016-05-20Completed
Temocillin Use in Complicated Urinary Tract Infections Due to Extended Spectrum Beta-Lactamases (ESBL) Producing and AmpC Hyperproducing Enterobacteriaceae in United Kingdom [NCT01543347]Phase 40 participants (Actual)Interventional2012-02-29Withdrawn(stopped due to No patient has been included in 9 months because of strict incl/excl criteria)
A Clinical Pharmacokinetic Study: Is Three Times Weekly Temocillin Appropriate for the Treatment of Severe Gram-negative Infections in Patients With ESRD Treated With Intermittent Hemodialysis? [NCT02285075]Phase 416 participants (Actual)Interventional2011-06-30Completed
Piperacillin-tazobactam and Temocillin as Carbapenem-alternatives for the Treatment of Severe Infections Due to Extended-spectrum Beta-lactamase-Producing Gram-negative Enterobacteriaceae in the Intensive Care Unit [NCT05565222]Phase 3600 participants (Anticipated)Interventional2023-03-11Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]