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）』「2013/11/26 16:12:15」(JST)
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Carbenicillin
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| 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
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InChI
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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
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Y (what is this?) (verify)
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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.
Contents
- 1 Pharmacology
- 2 Spectrum of bacterial susceptibility and resistance
- 3 Additional reading
- 4 Reference
Pharmacology[edit]
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[edit]
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 Susceptibility and Resistance data sheet.[1]
Additional reading[edit]
- 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[edit]
- ^ "Carbenicillin Susceptibility and Resistance data". Retrieved 14 July 2013.
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Antibacterials: cell envelope antibiotics (J01C-J01D)
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| Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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| Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
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Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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|
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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| Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
- Isoniazid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- Effect of tannic and gallic acids alone or in combination with carbenicillin or tetracycline on Chromobacterium violaceum CV026 growth, motility, and biofilm formation.
- Dusane DH1,2, O'May C2,2, Tufenkji N2,2.
- Canadian journal of microbiology.Can J Microbiol.2015 Jun 3:1-8. [Epub ahead of print]
- Chromobacterium violaceum is an opportunistic pathogen that causes infections that are difficult to treat. The goal of this research was to evaluate the effect of selected tannins (tannic acid (TA) and gallic acid (GA)) on bacterial growth, motility, antibiotic (carbenicillin, tetracycline) suscepti
- PMID 26039903
- CARB-17 Family of β-Lactamases Mediates Intrinsic Resistance to Penicillins in Vibrio parahaemolyticus.
- Chiou J1, Li R1, Chen S2.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Jun;59(6):3593-5. doi: 10.1128/AAC.00047-15. Epub 2015 Mar 23.
- Vibrio parahaemolyticus is commonly resistant to ampicillin, yet the mechanisms underlying this phenomenon are not clear. In this study, a novel class A carbenicillin-hydrolyzing β-lactamase (CARB) family of β-lactamases, blaCARB-17, was identified and found to be responsible for the intrinsic pen
- PMID 25801555
- Synthetic dendrimeric peptide active against biofilm and persister cells of Pseudomonas aeruginosa.
- Bahar AA1, Liu Z, Totsingan F, Buitrago C, Kallenbach N, Ren D.
- Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2015 May 27. [Epub ahead of print]
- Antimicrobial dendrimeric peptides (AMDP) are a relatively new class of agents displaying repetitive functional groups on a branched core. Previously, we have investigated the length requirement for antimicrobial activity of peptides consisting of repeated arginine (R) and tryptophan (W) side chains
- PMID 26012420
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
- 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
- 東福寺 英之
- 泌尿器科紀要 24(12), p1087-1093, 1978-12
- … Geopen U, an orally administered carbenicillin indanyl sodium belonging to the synthetic penicillin group, was administered to 34 cases of Pseudomonas infection and 5 cases of proteus group infection of the urinary tract with definite predisposing factors and the following results were obtained. …
- NAID 120002233369
- Geopen URとAlclofenacの急性膀胱炎に対する効果
- 和志田 裕人,上田 公介,渡辺 秀輝
- 泌尿器科紀要 23(3), p255-257, 1977-04
- Indanyl carbenicillin and alclofenac were administered to 42 female patients with acute cystitis at Department of Urology, Kosei Hospital, Anjo. 1. The clinical effects were as follows: excellent 28 c …
- NAID 120002233175
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