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Carbenicillin
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
Identifiers
CAS number 4697-36-3
ATC code J01CA03
PubChem 20824
DrugBank APRD00846
ChemSpider 19599
Chemical data
Formula C 17H18N2O6S 
Mol. mass 378.401 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability 30 to 40%
Protein binding 30 to 60%
Metabolism Minimal
Half life 1 hour
Excretion Renal (30 to 40%)
Therapeutic considerations
Pregnancy cat. B(US) Passes into breast milk
Legal status -only (US)
Routes Oral
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Carbenicillin is a bactericidal and 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.

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 benzyl-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 than analogous antibiotics like ampicillin. However, in most situations this is not a significant problem so ampicillin is used due to its lower cost.

Additional reading

  • Basker MJ, Comber KR, Sutherland R, Valler GH (1977). "Carfecillin: antibacterial activity in vitro and in vivo". Chemotherapy 23 (6): 424–35. 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.  







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