Carbenicillin

Carbenicillin
Clinical data
Trade namesGeocillin; Pyopen
Other namesCB[1]
AHFS/Drugs.comMonograph
Pregnancy
category
Routes of
administration		Oral, parenteral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30 to 40%
Protein binding30 to 60%
MetabolismMinimal
Elimination half-life1 hour
ExcretionRenal (30 to 40%)
Identifiers
  • (2S,5R,6R)-6-{[carboxy(phenyl)acetyl]amino}-
    3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]
    heptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.022.882 Edit this at Wikidata
Chemical and physical data
FormulaC17H18N2O6S
Molar mass378.40 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)O)[C@H]3SC2(C)C
  • InChI=1S/C17H18N2O6S/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25)/t9?,10-,11+,14-/m1/s1 checkY
  • Key:FPPNZSSZRUTDAP-UWFZAAFLSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Carbenicillin is a bactericidal antibiotic belonging to the carboxypenicillin subgroup of the penicillins.[2] 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

The antibiotic is highly soluble in water and is acid-labile. A typical lab working concentration is 50 to 100 μg per mL.[citation needed]

It is a semi-synthetic analogue of the naturally occurring benzylpenicillin. 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.[citation needed]

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.[citation needed]

Spectrum of bacterial susceptibility and resistance

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.[3] 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

References

  1. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  2. ^ 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.
  3. ^ "Carbenicillin Disodium, USP Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). January 6, 2020.

Further reading

  • 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.