geocillin

カルベニシリン carbenicillin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/26 18:02:21」(JST)

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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 Y
ATC code	J01CA03
PubChem	CID 20824
DrugBank	DB00578
ChemSpider	19599 Y
UNII	G42ZU72N5G Y
ChEBI	CHEBI:3393 Y
ChEMBL	CHEMBL1214 Y
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 Y Key:FPPNZSSZRUTDAP-UWFZAAFLSA-N Y
Y (what is this?)  (verify)

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 very 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 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.

Spectrum of bacterial susceptibility and resistance

Most of the bacteria like Burkholderia,Escherichia coli,Pseudomonas and Salmonella have developed resistance toward Carbenicillin. Some of Staphylococcus developed resistance to Carbenicillin and some of them are susceptible to it. For the detailed information about the MIC of Carbenicillin, please refer to Carbenicillin Susceptibilty and Resistance data sheet.

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. 

Reference

UpToDate Contents

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• 1. ペニシリン penicillins
• 2. アエロモナス感染症 aeromonas infections
• 3. プレジオモナス・シゲロイデス感染症 plesiomonas shigelloides infections
• 4. 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
• 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.
• OBJECTIVE: Lavage techniques are used every day all over the world to clean wounds and surgical approaches. The solutions used vary depending on the application range; there are, for instance, normal saline, antibiotic or antiseptic solutions. This review describes the lavage solutions actually used
• 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.
• Three new Lycopodium alkaloids, carinatumins A-C (1-3), have been isolated from the club moss Lycopodium carinatum. Structures and stereochemistry of 1-3 were elucidated on the basis of 2D NMR correlations. Carinatumins A (1) and B (2) exhibited a potent inhibitory activity against acetylcholinester
• 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.
• Transport of carbenicillin (CBPC) and its orally active prodrug (carindacillin, CIPC) was studied with rat intestinal brush border membrane vesicles (BBMV). CIPC was transported uphill into BBMV in the presence of a H(+) gradient, indicating that CIPC absorption is carrier-mediated. Indeed, CIPC was
• PMID 10564841

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