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Temocillin

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Dec 15, 2021

Temocillin is a β-lactamase-resistant penicillin[1][2] introduced by Beecham, marketed by Eumedica Pharmaceuticals as Negaban. It is used primarily for the treatment of multiple drug-resistant, Gram-negative bacteria.
It is a 6-methoxy penicillin; it is also a carboxypenicillin.[3]

Temocillin
Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Identifiers
  • (2S,5R,6S)-6-[(Carboxy-3-thienylacetyl)amino]- 6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylic acid,
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)
  • O=C(O)[C@@H]2N3C(=O)[C@@](OC)(NC(=O)C(c1ccsc1)C(=O)O)[C@H]3SC2(C)C
  • InChI=1S/C16H18N2O7S2/c1-15(2)9(12(22)23)18-13(24)16(25-3,14(18)27-15)17-10(19)8(11(20)21)7-4-5-26-6-7/h4-6,8-9,14H,1-3H3,(H,17,19)(H,20,21)(H,22,23)/t8?,9-,14+,16-/m0/s1 Y
  • Key:BVCKFLJARNKCSS-DWPRYXJFSA-N Y

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. . . Temocillin . . .

Temocillin is a β-lactamase-resistant penicillin. It is not active against Gram-positive bacteria or bacteria with altered penicillin-binding proteins.

It is normally active against Moraxella catarrhalis, Brucella abortus, Burkholderia cepacia, Citrobacter species, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Pasteurella multocida, Proteus mirabilis, Salmonella typhimurium, and Yersinia enterocolitica. It is also active against some Enterobacter species, Morganella morganii, and Serratia species. Temocillin has no useful activity against Acinetobacter species or Pseudomonas aeruginosa.

Its primary use is against Enterobacteriaceae, and in particular against strains producing extended-spectrum β-lactamase or AmpC β-lactamase.[4]

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:[5][6] 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.

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.

. . . Temocillin . . .

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. . . Temocillin . . .