Carbenicillin

drugbox
IUPAC_name = (2"S",5"R",6"R")-6-{ [carboxy(phenyl)acetyl] amino}-
3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]
heptane-2-carboxylic acid

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CAS_number = 4697-36-3
ATC_prefix = J01
ATC_suffix = CA03
ATC_supplemental =
PubChem = 20824
DrugBank = APRD00846
C = 17 | H = 18 | N = 2 | O = 6 | S = 1
molecular_weight = 378.401 g/mol
bioavailability = 30 to 40%
protein_bound = 30 to 60%
metabolism = Minimal
elimination_half-life = 1 hour
excretion = Renal (30 to 40%)
pregnancy_US = B
pregnancy_category = Passes into breast milk
legal_US = Rx-only
routes_of_administration = Oral

Carbenicillin is an antibiotic belonging to the carboxypenicillin subgroup of the penicillins. It has gram-negative coverage which includes "Pseudomonas aeruginosa" but limited gram-positive coverage. The carboxypenicillins are susceptible to degradation by beta-lactamase enzymes, although they are more resistent than ampicillin to degradation. Carbenicillin is also more stable at lower pH than ampicillin.

The antibiotic is very soluble in water and is acid-labile. Aqueous solutions are short-lived. Working concentration in the lab: up to 100 µg per ml.

It is a semi-synthetic analogue of the naturally occurring penicillin.

In molecular biology, Carbenicillin may be preferred as a selecting agent (see Plasmid stabilisation technology) because its breakdown results in byproducts with a lower toxicity to analogous antibiotics like ampicillin.

Additional Reading:

Carfecillin: antibacterial activity in vitro and in vivo. Basker MJ, Comber KR, Sutherland R, Valler GH. Chemotherapy. 1977;23(6):424-35. PMID: 21771 [http://www.ncbi.nlm.nih.gov/pubmed/21771]

Kinetics of drug decomposition. Part 66. Kinetics of the hydrolysis of carphecillin in aqueous solution. Pawełczyk E, Zajac M, Knitter B, Mikołajczak P. Pol J Pharmacol Pharm. 1981 Oct;33(3):373-86. PMID: 7322950 [http://www.ncbi.nlm.nih.gov/pubmed/7322950]

it is mostly given as sodium saltin a dose of 1-2g i.m or 1-5g i.v.At higher doses Na conc.increase in body and precipitate CHf and causes fluid retension.high doses also causes pletlet dysfunction.