Carbenicillin

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Carbenicillin
Carbenicillin.svg
Systematic (IUPAC) name
(2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-
3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]
heptane-2-carboxylic acid
Clinical data
Trade names Geocillin
AHFS/Drugs.com monograph
Pregnancy cat. B (US) Passes into breast milk
Legal status -only (US)
Routes Oral, parenteral
Pharmacokinetic data
Bioavailability 30 to 40%
Protein binding 30 to 60%
Metabolism Minimal
Half-life 1 hour
Excretion Renal (30 to 40%)
Identifiers
CAS number 4697-36-3 YesY
ATC code J01CA03
PubChem CID 20824
DrugBank DB00578
ChemSpider 19599 YesY
UNII G42ZU72N5G YesY
ChEBI CHEBI:3393 YesY
ChEMBL CHEMBL1214 YesY
Chemical data
Formula C17H18N2O6S 
Mol. mass 378.401 g/mol
 YesY (what is this?)  (verify)

Carbenicillin is a bacteriolytic antibiotic belonging to the carboxypenicillin subgroup of the penicillins. It was discovered by scientists at Beecham and marketed as Pyopen. 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 resistant than ampicillin to degradation. Carbenicillin is also more stable at lower pH than ampicillin.

Pharmacology[edit]

The antibiotic is highly soluble in water and is acid-labile. A typical lab working concentration is 100 µg per ml.

It is a semi-synthetic analogue of the naturally occurring benzyl-penicillin. Carbenicillin at high doses can cause bleeding. Use of carbenicillin can cause hypokalemia by promoting potassium loss at the distal convoluted tubule of the kidney.

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 than analogous antibiotics like ampicillin. Carbenicillin is more stable than ampicillin and results in fewer satellite colonies on selection plates. However, in most situations this is not a significant problem so ampicillin is sometimes used due to its lower cost.

Spectrum of bacterial susceptibility and resistance[edit]

Carbenicillin has been shown to be effective against bacteria responsible for causing urinary tract infections including Pseudomonas aeruginosa, Escherichia coli, and some Proteus species. The following represents carbenicillin susceptibility data for a few medically significant organisms. This is not representative of all species of bacteria susceptible to carbenicillin exposure.

  • Escherichia coli 1.56 μg/ml - 64 μg/ml
  • Proteus mirabilis 1.56 μg/ml - 3.13 μg/ml
  • Pseudomonas aeruginosa 3.13 μg/ml - >1024 μg/ml

[1]

Additional reading[edit]

  • Basker MJ, Comber KR, Sutherland R, Valler GH (1977). "Carfecillin: antibacterial activity in vitro and in vivo". Chemotherapy 23 (6): 424–35. doi:10.1159/000222012. PMID 21771. 
  • Pawełczyk E, Zajac M, Knitter B, Mikołajczak P (October 1981). "Kinetics of drug decomposition. Part 66. Kinetics of the hydrolysis of carphecillin in aqueous solution". Polish journal of pharmacology and pharmacy 33 (3): 373–86. PMID 7322950. 

References[edit]