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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/22 20:59:13」(JST)

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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 penicillins
2. プレジオモナス・シゲロイデス感染症 plesiomonas shigelloides infections
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. アエロモナス感染症 aeromonas infections
5. 嫌気性細菌感染 anaerobic bacterial infections

English Journal

Purification and characterization of a new β-lactamase OXA-205 from Pseudomonas aeruginosa.

Krasauskas R1, Labeikytė D2, Markuckas A3, Povilonis J4,5, Armalytė J6, Plančiūnienė R7, Kavaliauskas P8, Sužiedėlienė E9.
Annals of clinical microbiology and antimicrobials.Ann Clin Microbiol Antimicrob.2015 Nov 26;14(1):52. doi: 10.1186/s12941-015-0113-1.
BACKGROUND: We have identified a novel class 1 integron (1503 bp), named In671 in a clinical Pseudomonas aeruginosa isolate. Integron sequence analysis revealed two gene cassettes, one coding for a new OXA-type β-lactamase designated as OXA-205 and the other coding for the aadB gene that is respon
PMID 26611758

Physiological Function of Rac Prophage During Biofilm Formation and Regulation of Rac Excision in Escherichia coli K-12.

Liu X1, Li Y1,2, Guo Y1, Zeng Z1,2, Li B1,2, Wood TK3,4, Cai X1, Wang X1.
Scientific reports.Sci Rep.2015 Nov 4;5:16074. doi: 10.1038/srep16074.
Rac or rac-like prophage harbors many genes with important physiological functions, while it remains excision-proficient in several bacterial strains including Escherichia coli, Salmonella spp. and Shigella spp. Here, we found that rac excision is induced during biofilm formation, and the isogenic s
PMID 26530864

Utility of surface enhanced Raman spectroscopy (SERS) for elucidation and simultaneous determination of some penicillins and penicilloic acid using hydroxylamine silver nanoparticles.

El-Zahry MR1, Refaat IH2, Mohamed HA2, Rosenberg E3, Lendl B3.
Talanta.Talanta.2015 Nov 1;144:710-6. doi: 10.1016/j.talanta.2015.07.015. Epub 2015 Jul 10.
Elucidation and quantitative determination of some of commonly used penicillins (ampicillin, penicillin G and carbenicillin) in the presence of their main degradation product (penicilloic acid) were developed. Forced acidic and basic degradation processes were applied at different time intervals. Th
PMID 26452881

Japanese Journal

Agrobacterium-Mediated Transformation of Euphorbia tirucalli Callus

UCHIDA Hidenobu,YAMASHITA Hirofumi,ANAI Toyoaki,MURANAKA Toshiya,OHYAMA Kanji
Bioscience, biotechnology, and biochemistry 74(4), 851-853, 2010-04-23
… petroleum plant Euphorbia tirucalli, the callus of the plant was infected with Agrobacterium, washed with distilled water, sterilized with distilled water containing 100 mg/l of carbenicillin, selected on solidified B5 medium containing 13 mg/l of G418 and 100 mg/l of carbenicillin, and then on solidified B5 medium containing 25 mg/l of G418 and 100 mg/l of carbenicillin for the transgenic calli, and then the callus lines were subcultured successively on solidified B5 medium containing 50 mg/l of …
NAID 10027554214

リンゴの形質転換におけるAgrobacterium除菌用抗生物質の検討

小森貞男,渡邉麻紗乃,渡邉学 [他]
園芸学研究 8(4), 419-426, 2009-10-15
… Agrobacterium法によるリンゴの形質転換体作出の際に用いる除菌用抗生物質の検討を行った．供試した抗生物質はCarbenicillin（CBPC），Clavulanic acid/Amoxicillin（CVA/AMPC），Cefotaxime（CTX），Meropenem（MEPM），Vancomycin（VCM）およびDoxycycline（DOXY）の6種類である．Agrobacterium tumefaciens EHA101の増殖はCBPCが1,500 mg・L−1，CVA/AMPC 750 mg・L−1，CTX 500 mg・L−1以下，MEPM 50 mg・L−1，DOXY 200 mg・L−1で抑制され，VCMでは1500 mg・L−1でも抑制できなか …
NAID 120001904617

Related Pictures

★リンクテーブル★

リンク元	「カルベニシリン」「geocillin」「geopen」
拡張検索	「carbenicillin sodium」

「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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