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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.

Pharmacology

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

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

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

^ http://www.toku-e.com/Assets/MIC/Carbenicillin%20disodium%20USP.pdf

UpToDate Contents

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1. ペニシリン penicillins
2. アミノグリコシドによる腎毒性の症状および危険因子 manifestations of and risk factors for aminoglycoside nephrotoxicity
3. プレジオモナス・シゲロイデス感染症 plesiomonas shigelloides infections
4. アエロモナス感染症 aeromonas infections
5. 嫌気性細菌感染 anaerobic bacterial infections

English Journal

Use of lavage fluids in arthroplasty to prevent postoperative infections.

Kruckenhauser EM1, Nogler M1, Coraça-Huber D1.
Drug research.Drug Res (Stuttg).2014 Mar;64(3):166-8. doi: 10.1055/s-0033-1354367. Epub 2013 Aug 28.
PMID 23986306

Carinatumins A-C, new alkaloids from Lycopodium carinatum inhibiting acetylcholinesterase.

Choo CY1, Hirasawa Y, Karimata C, Koyama K, Sekiguchi M, Kobayashi J, Morita H.
Bioorganic & medicinal chemistry.Bioorg Med Chem.2007 Feb 15;15(4):1703-7. Epub 2006 Dec 15.
PMID 17188496

Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model.

Li YH1, Tanno M, Itoh T, Yamada H.
International journal of pharmaceutics.Int J Pharm.1999 Nov 30;191(2):151-9.
PMID 10564841

Related Pictures

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リンク元	「カルベニシリン」
関連記事	「geocillin」「GEOCILLIN」

「カルベニシリン」

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
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
ATC code	J01CA03
PubChem	CID 20824
DrugBank	DB00578
ChemSpider	19599
UNII	G42ZU72N5G
ChEBI	CHEBI:3393
ChEMBL	CHEMBL1214
Chemical data
Formula	C17H18N2O6S
Mol. mass	378.401 g/mol
	SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)C(c1ccccc1)C(=O)O)[C@H]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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