 | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | International Drug Names |
| ATC code | |
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| ChemSpider |
|
| UNII | |
| KEGG |
|
| ChEBI | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.060.148 |
| Chemical and physical data | |
| Formula | C16H18N2O7S2 |
| Molar mass | 414.45 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Temocillin is aβ-lactamase-resistantpenicillin[1][2] introduced byBeecham, marketed by Eumedica Pharmaceuticals as Negaban. It is used primarily for the treatment of multiple drug-resistant,Gram-negative bacteria.
It is actually a 6-methoxyTicarcillin; it is also acarboxypenicillin.[3]
Temocillin is a β-lactamase-resistant penicillin. It is not active againstGram-positive bacteria or bacteria with alteredpenicillin-binding proteins.[citation needed]
It is normally active againstMoraxella catarrhalis,Brucella abortus,Burkholderia cepacia,Citrobacter species,Escherichia coli,Haemophilus influenzae,Klebsiella pneumoniae,Pasteurella multocida,Proteus mirabilis,Salmonella typhimurium, andYersinia enterocolitica. It is also active against someEnterobacter species,Morganella morganii, andSerratia species. Temocillin has no useful activity againstAcinetobacter species orPseudomonas aeruginosa.[4]
Its primary use is againstEnterobacteriaceae, and in particular against strains producingextended-spectrum β-lactamase orAmpC β-lactamase.[5] Temocillin is also usually active against KPC-producingK. pneumoniae, and synergistic activity has been demonstrated when administered alongside fosfomycin.[6]
Temocillin has also been reported in the management of urinary tract, bloodstream and intra-abdominal infections, with a favorable safety and ecological profile. It has additionally been used in outpatient parenteral antimicrobial therapy (OPAT), including administration by the subcutaneous route.[7]
The common dose is 2 g intravenously every 12 hours and the high dose, notably in critically ill patients, is 2g every 8 hours. Theoretical reasons exist for giving temocillin as a continuous intravenous infusion in severe disease[8][9] a single loading dose of 2 g is given intravenously followed by a 4-g or 6-g infusion over 24 hours. According to the SPC, chemical and physical in-use stability has been demonstrated for 24 hours at 25 °C for the following solvents: water for injection, physiological saline (0.9% sodium chloride), dextrose 5%, sodium chloride compound (Ringer's solution), Hartmann solution (sodium lactate compound + Ringer's lactate solution). Temocillin for intravenous injection is diluted in 10 to 20 ml of sterile water; it is diluted in less than 2 ml of sterile water when being prepared for intramuscular injection; the continuous infusion is diluted in 48 ml of sterile water for ease of administration (2 ml per hour). To reduce pain, the intramuscular injection may be made up using sterile 1% lignocaine instead of sterile water.[citation needed]Subcutaneous administration of temocillin, although off-label, has been investigated in selected patients, showing lower peak concentrations but sustained plasma exposure above pharmacokinetic/pharmacodynamic targets over the dosing interval, with limited clinical data suggesting feasibility and tolerability in outpatient parenteral antimicrobial therapy (OPAT) settings.[10]
Temocillin may be given to patients with impaired renal function after the dose has been adapted:
| Creatinine clearance (mL/min) | Dosage per administration | Interval between administrations |
|---|---|---|
| More than 60 | 2 g | 12 h |
| 60 to 30 | 1 g | 12 h |
| 30 to 10 | 1 g | 24 h |
In case of intermittent high-flux hemodialysis: 1 g (I.V. injection) per 24 h of inter-dialytic session, preferably at the end of the hemodialysis (1 g q24 h, 2 g q48 h, 3 g q72 h).In case of continuous peritoneal dialysis in ambulatory patients: 1 g every 24 hours.
No oral preparation of temocillin is licensed.
The undesirable effects of temocillin are those of any β-lactam antibiotic. In particular, it has been associated with angioedema and anaphylaxis in penicillin-allergic patients. Animal studies have not shown any induction ofClostridioides difficile infection.[11] As with any other penicillin, convulsions can occur if very high doses are given.[citation needed]
