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Carbenicillin


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
Chemical data
Formula	C₁₇H₁₈N₂O₆S
Mol. mass	378.401 g/mol
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

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.

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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. Although much more expensive than ampicillin, it is much more stable.

v • d • e Antibacterials for systemic use: beta-lactam antibiotics - penicillins (J01C)
Antibiotics	Amoxicillin • Ampicillin • Azlocillin • Carbenicillin • Cloxacillin • Dicloxacillin • Flucloxacillin • Mezlocillin • Nafcillin • Piperacillin • Pivampicillin • Ticarcillin
Beta-lactamase inhibitors	Sulbactam • Tazobactam • Clavulanic acid
Combinations	Ampicillin/sulbactam (Sultamicillin) • Co-amoxiclav