Synonyms: BRL-2064; Carbenicilina sódica; Carbenicillin Disodium (USAN); Carbénicilline sodique; Carbenicillinum natricum; zylpenicillin Sodium; CP-15-6392; GS-3159 (carbenicillin potassium); Karbenicillin-nátrium; Karbenicylina sodowa; Natrii Carbenicillinum; NSC-111071. The disodium salt of (6R)-6-(2-carboxy2-phenylacetamido)penicillanic acid .
Cyrillic synonym: Натрий Карбенициллин.
💊 Chemical information
Chemical formula: C17H16N2Na2O6S = 422.4.
CAS — 4697-36-3 (carbenicillin); 4800-94-6 (carbenicillin disodium); 17230-86-3 (carbenicillin potassium).
ATC — J01C A03.
ATC Vet — QJ01CA03.
Pharmacopoeias.In Pol. and US.
USP 31(Carbenicillin Disodium). A white to off-white crystalline powder. Freely soluble in water; soluble in alcohol; practically insoluble in chloroform and in ether. pH of a solution in water containing the equivalent of carbenicillin 1% is between 6.5 and 8.0. Store in airtight containers.
Incompatibility.Carbenicillin sodium has been reported to be incompatible with aminoglycosides, tetracyclines, and a number of other drugs including other antimicrobials and these drugs should therefore be given separately.
💊 Adverse Effects
As for Benzylpenicillin. Hypersensitivity reactions have been reported to be less frequent and less severe with carbenicillin than with benzylpenicillin. Pain at the injection site and phlebitis may occur. Electrolyte disturbances, particularly hypokalaemia or hypernatraemia, may follow large doses of carbenicillin sodium. A dose-dependent coagulation defect has been reported, especially in patients with renal impairment. Carbenicillin appears to interfere with platelet function thereby prolonging bleeding time; purpura and haemorrhage from mucous membranes and elsewhere may result.
As for Benzylpenicillin.
Sodium content.Each g of carbenicillin sodium contains about 4.7 mmol of sodium. Carbenicillin sodium should therefore be given with caution to patients on a restricted sodium diet.
As for Benzylpenicillin.
💊 Antimicrobial Action
Carbenicillin has a bactericidal mode of action similar to that of benzylpenicillin, but with an extended spectrum of activity against Gram-negative bacteria. The most important feature of carbenicillin is its activity against Pseudomonas aeruginosa, although high concentrations are generally necessary. Activity against Ps. aeruginosa and some other organisms can be enhanced by gentamicin and other aminoglycosides. Carbenicillin is also active against Proteus, including indole-positive spp. such as Pr. vulgaris. It is comparable with ampicillin against other Gram-negative bacteria. Sensitive organisms include some Enterobacteriaceae, for example Escherichia coli and Enterobacter spp.; Haemophilus influenzae; and Neisseria spp. Klebsiella spp. are usually not susceptible. Its activity against Gram-positive bacteria is less than that of benzylpenicillin. Anaerobic organisms are generally susceptible to carbenicillin, but high concentrations are required for Bacteroides fragilis. Resistance. Carbenicillin is inactivated by penicillinases and some other beta-lactamases, although it is more stable to the chromosomally mediated beta-lactamases produced by some Gram-negative organisms, including Ps. aeruginosa and some Proteus spp. Resistance to carbenicillin may develop in Ps. aeruginosa during treatment with carbenicillin or other beta lactams. This resistance may be intrinsic where there are changes in cell wall permeability or penicillin-binding proteins, or it may be due to plasmid-mediated beta-lactamase production that may be transferred to and from certain strains of Enterobacteriaceae. There may be cross-resistance between carbenicillin and other antipseudomonal penicillins. Outbreaks of pseudomonal resistance to carbenicillin have been associated with extensive use in, for example, hospital burns units.
Carbenicillin is not absorbed from the gastrointestinal tract and has therefore been given either intramuscularly or intravenously. The half-life of carbenicillin is reported to be about 1 to 1.5 hours; it is increased in patients with renal impairment, especially if there is also hepatic impairment, and also in neonates. Halflives of 10 to 18 hours have been reported in renal impairment. Clearance is enhanced in patients with cystic fibrosis. Carbenicillin is about 50% bound to plasma proteins. Distribution of carbenicillin in the body is similar to that of other penicillins. Small amounts have been detected in breast milk. There is little diffusion into the CSF except when the meninges are inflamed. Relatively high concentrations have been reported in bile, but carbenicillin is excreted principally by renal tubular secretion and glomerular filtration. Probenecid increases and prolongs plasma concentrations of carbenicillin. Carbenicillin is removed by haemodialysis and, to some extent, by peritoneal dialysis.
💊 Uses and Administration
Carbenicillin is a carboxypenicillin that has been given by injection as the disodium salt, often with gentamicin, in the treatment of infections due to Pseudomonas aeruginosa; however, other antipseudomonal penicillins such as ticarcillin or piperacillin are now preferred. It has also been given to treat serious infections due to non-penicillinase-producing strains of Proteus spp. Esters of carbenicillin, such as carfecillin and carindacillin, have been given orally in the treatment of urinarytract infections.
USP 31: Carbenicillin for Injection.
Proprietary PreparationsMex.: Carbecin†.
Published December 11, 2018.