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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 50 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、黄色ブドウ球菌用ペニシリン、広域ペニシリン penicillin antistaphylococcal penicillins and broad spectrum penicillins
2. ペニシリンアレルギーのある入院患者への抗菌薬の選択 choice of antibiotics in penicillin allergic hospitalized patients
3. 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
4. Causes of hypokalemia in adults
5. プレジオモナス・シゲロイデス感染症 plesiomonas shigelloides infections

English Journal

SERS investigation and high sensitive detection of carbenicillin disodium drug on the Ag substrate.

Jiang X1, Chen Y1, Du J1, Yang M1, Shen Y1, Li X1, Han X2, Yang L3, Zhao B4.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2018 Nov 5;204:241-247. doi: 10.1016/j.saa.2018.06.059. Epub 2018 Jun 18.
PMID 29936221

Relation to enterocins of variable Aeromonas species isolated from trouts of Slovakian aquatic sources and detected by MALDI-TOF mass spectrometry.

Lauková A1, Kubašová I2, Kandričáková A2, Strompfová V2, Žitňan R3, Simonová MP2.
Folia microbiologica.Folia Microbiol (Praha).2018 Nov;63(6):749-755. doi: 10.1007/s12223-018-0616-1. Epub 2018 May 28.
PMID 29808450

Do plastics serve as a possible vector for the spread of antibiotic resistance? First insights from bacteria associated to a polystyrene piece from King George Island (Antarctica).

Laganà P1, Caruso G2, Corsi I3, Bergami E4, Venuti V5, Majolino D6, La Ferla R7, Azzaro M8, Cappello S9.
International journal of hygiene and environmental health.Int J Hyg Environ Health.2018 Aug 30. pii: S1438-4639(18)30425-5. doi: 10.1016/j.ijheh.2018.08.009. [Epub ahead of print]
PMID 30174218

Japanese Journal

緑膿菌感染症に対する Geopen-U の臨床治験 : 第46回山陰地方会

日本泌尿器科學會雜誌 74(2), 263, 1983
NAID 110003081759

慢性難治性尿路感染症におけるCarbenicillin indanyl Sodium(Geopen U錠)の経口投与による臨床経験--主としてPseudomonas,Proteus属による感染症として

泌尿器科紀要 24(12), p1087-1093, 1978-12
NAID 120002233369

Geopen URとAlclofenacの急性膀胱炎に対する効果

泌尿器科紀要 23(3), p255-257, 1977-04
NAID 120002233175

Related Pictures

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★リンクテーブル★

リンク元	「カルベニシリン」
関連記事	「geopen」

「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; category	US: B (No risk in non-human studies); Passes into breast milk;
Legal status	US: ℞-only;
Routes of; administration	Oral, parenteral
Pharmacokinetic data
Bioavailability	30 to 40%
Protein binding	30 to 60%
Metabolism	Minimal
Biological half-life	1 hour
Excretion	Renal (30 to 40%)
Identifiers
CAS Registry 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
Molecular 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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