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Carbenicillin

Clinical data
Trade names	Geocillin
AHFS/Drugs.com	Monograph
Pregnancy category	Passes into breast milk
Routes of administration	Oral
ATC code	J01CA03 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	30 to 40%
Protein binding	30 to 60%
Metabolism	Minimal
Elimination half-life	1 hour
Excretion	Renal (30 to 40%)
Identifiers
IUPAC name (2S,5R,6R)-6-{amino}- 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo heptane-2-carboxylic acid
CAS Number	4697-36-3
PubChem CID	20824
DrugBank	DB00578
ChemSpider	19599
UNII	G42ZU72N5G
ChEBI	CHEBI:3393
ChEMBL	ChEMBL1214
CompTox Dashboard (EPA)	DTXSID6048464
ECHA InfoCard	100.022.882
Chemical and physical data
Formula	C17H18N2O6S
Molar mass	378.401 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(O)2N3C(=O)(NC(=O)C(c1ccccc1)C(=O)O)3SC2(C)C
InChI 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 Key:FPPNZSSZRUTDAP-UWFZAAFLSA-N
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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.

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. Carbenicillin is more stable than ampicillin and results in less 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.

Additional reading

• 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

• Pawełczyk E, Zajac M, Knitter B, Mikołajczak P (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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