セフロキシム
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/01/10 14:58:58」(JST)
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Cefuroxime
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Systematic (IUPAC) name |
(6R,7R)-3-{[(aminocarbonyl)oxy]methyl}-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino) acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
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Clinical data |
Trade names |
Zinacef, Ceftin |
MedlinePlus |
a601206 |
Pregnancy
category |
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Legal status |
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Routes of
administration |
intramuscular, intravenous |
Pharmacokinetic data |
Bioavailability |
37% on an empty stomach, up to 52% if taken after food |
Biological half-life |
80 minutes |
Excretion |
Urine 66–100% unchanged |
Identifiers |
CAS Number |
55268-75-2 Y |
ATC code |
J01DC02 S01AA27 QJ51DC02 |
PubChem |
CID: 5361202 |
DrugBank |
DB01112 Y |
ChemSpider |
4514699 Y |
UNII |
O1R9FJ93ED Y |
KEGG |
D00262 Y |
ChEMBL |
CHEMBL466 Y |
Chemical data |
Formula |
C16H16N4O8S |
Molecular mass |
424.386 g/mol |
SMILES
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O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3occc3)COC(=O)N)C(=O)O
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InChI
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InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9+/t10-,14-/m1/s1 Y
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Key:JFPVXVDWJQMJEE-SWWZKJRFSA-N Y
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(verify) |
Cefuroxime is an enteral second-generation cephalosporin antibiotic. It was discovered by the Glaxo, now GlaxoSmithKline and first marketed in 1978 as Zinacef. It received approval from the U.S. Food and Drug Administration in October of 1983.[1]
Cefuroxime axetil is an acetoxyetyl-ester-prodrug of cefuroxime which is effective orally.[2]
Contents
- 1 Medical uses
- 2 Side effects
- 3 Trade names
- 4 See also
- 5 References
Medical uses
As with the other cephalosporins, although as a second-generation variety, it is less susceptible to beta-lactamase. Hence, it may have greater activity against Haemophilus influenzae, Neisseria gonorrhoeae, and Lyme disease. Unlike most other second-generation cephalosporins, cefuroxime can cross the blood-brain barrier.
Side effects
Cefuroxime is generally well-tolerated and its side effects are usually transient. If ingested after food, this antibiotic is both better absorbed and less likely to cause its most common side effects of diarrhea, nausea, vomiting, headaches/migraines, dizziness, and abdominal pain compared to most antibiotics in its class.[citation needed]
Although a widely stated cross-allergic risk of about 10% exists between cephalosporins and penicillin, recent assessments have shown no increased risk for a cross-allergic reaction for cefuroxime and several other second-generation or later cephalosporins.[3]
Trade names
In US it is available as Zinacef by Covis Pharmaceuticals as the company acquired the US rights of the product from GSK.[4] In Bangladesh it is available as Xorimax by Sandoz. In India it is available as Supacef by GSK.[5] In Poland it is available as Zamur by Mepha, subsidiary of Teva Pharmaceutical Industries.[6]
See also
References
- ^ "Cefuroxime medical facts from". Drugs.com.
- ^ Walter Sneader. "Drug Discovery: History".
- ^ Pichichero ME (2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of family practice 55 (2): 106–12. PMID 16451776.
- ^ http://www.covispharma.ch/assets/pdf/covis-pharma-acquires-portfolio-of-drugs-from-glaxosmithkline.pdf
- ^ "GlaxoSmithKline Pharmaceuticals Limited – Prescription Medicines – Anti-Infective". Gsk-india.com. 26 March 2013.
- ^ "Charakterystyka produktu lecznicznego" (PDF). Urząd Rejestracji Produktów Leczniczych, Wyrobów Medycznych i Produktów Biobójczych. 12 November 2015.
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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Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of bacterial disease
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Description |
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Disease |
- Gram-positive firmicutes
- Gram-positive actinobacteria
- Gram-negative proteobacteria
- Gram-negative non-proteobacteria
- Cholera
- Tuberculosis
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Treatment |
- Antibiotics
- cell wall
- nucleic acid
- mycobacteria
- protein synthesis
- other
- Antibodies
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GlaxoSmithKline
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Subsidiaries |
- GlaxoSmithKline Pakistan
- GlaxoSmithKline Pharmaceuticals Ltd
- Stiefel Laboratories
- ViiV Healthcare (85%)
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Predecessors,
acquisitions |
- Allen & Hanburys
- Beecham Group
- Block Drug
- Burroughs Wellcome
- Glaxo
- Glaxo Wellcome
- Human Genome Sciences
- Recherche et Industrie Thérapeutiques
- Reliant Pharmaceuticals
- S. E. Massengill Company
- SmithKline Beecham
- Smith, Kline & French
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Products |
Current
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Pharmaceuticals
|
- Advair
- Alli
- Augmentin
- Avandia
- Beconase
- Boniva
- Flixonase
- Hycamtin
- Lamictal
- Paxil/Seroxat
- Serlipet
- Tagamet
- Ventolin
- Wellbutrin/Zyban
- Zantac … more
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Vaccines
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- Hepatyrix
- Pandemrix
- Twinrix
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Other
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- Aquafresh
- Horlicks
- Nicoderm
- Nicorette
- NiQuitin
- Sensodyne
- Tums … more
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|
|
Former
|
- BC Powder
- Geritol
- Goody's Powder
- Lucozade
- Ribena
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People |
Governance
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- Chris Gent (chair)
- Andrew Witty (CEO)
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Other
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- Thomas Beecham
- Silas M. Burroughs
- Mahlon Kline
- John K. Smith
- Henry Wellcome
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Litigation |
- Canada v. GlaxoSmithKline Inc.
- Christopher v. SmithKline Beecham Corp.
- GlaxoSmithKline Services Unlimited v Commission
- United States v. Glaxo Group Ltd.
- United States v. GlaxoSmithKline
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Other |
- Drug Industry Document Archive
- GlaxoSmithKline Prize
- Side Effects
- Study 329
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UpToDate Contents
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English Journal
- In vitro susceptibility of European human Borrelia burgdorferi sensu stricto strains to antimicrobial agents.
- Veinović G, Cerar T, Strle F, Lotrič-Furlan S, Maraspin V, Cimperman J, Ružić-Sabljić E.SourceDepartment of Microbiology and Immunology, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11221 Belgrade, Serbia.
- International journal of antimicrobial agents.Int J Antimicrob Agents.2013 Mar;41(3):288-91. doi: 10.1016/j.ijantimicag.2012.11.016. Epub 2013 Jan 9.
- Broth microdilution and macrodilution assays were used to determine minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) of six antimicrobial agents (ceftriaxone, cefuroxime sodium, azithromycin, amoxicillin, doxycycline and amikacin) for nine European human isolat
- PMID 23312603
- An 11-year analysis of the prevalent uropathogens and the changing pattern of Escherichia coli antibiotic resistance in 38,530 community urinary tract infections, Dublin 1999-2009.
- Cullen IM, Manecksha RP, McCullagh E, Ahmad S, O'Kelly F, Flynn R, McDermott TE, Murphy P, Grainger R, Fennell JP, Thornhill JA.SourceDepartment of Urology, AMNCH, Tallaght, Dublin 24, Ireland. imcullen@gmail.com
- Irish journal of medical science.Ir J Med Sci.2013 Mar;182(1):81-9. doi: 10.1007/s11845-012-0834-5. Epub 2012 Jun 6.
- BACKGROUND: Knowledge of local antimicrobial resistance patterns is essential for evidence-based empirical antibiotic prescribing, and a cutoff point of 20% has been suggested as the level of resistance at which an agent should no longer be used empirically. We sought to identify the changing incide
- PMID 22669684
- Analysis of the effect of integrons on drug-resistant Staphylococcus aureus by multiplex PCR detection.
- Ren C, Zhao Y, Shen Y.SourceDepartment of Clinical Laboratory, The First Affiliated Hospital of Zhengzhou University, Zhengzhou, Henan 450052, P.R. China.
- Molecular medicine reports.Mol Med Rep.2013 Mar;7(3):719-24. doi: 10.3892/mmr.2013.1284. Epub 2013 Jan 21.
- The aim of this study was to detect class Ⅰ, II and III integrons using multiplex PCR, and to analyze the role that these integrons play in mediating multidrug-resistant Staphylococcus aureus (SA). The sensitivity of SA to 20 types of antibiotics was examined
- PMID 23337960
Japanese Journal
- 村瀬 勢津子,落合 かおり,青木 路恵,朝長 文弥
- 病院薬学 13(4), 244-260, 1987-08-20
- … Mixing with following injections should be avoided: Neophylin, Soldactone, Lasix, Horizone, Solu-cortef, Hydrocortone, Decadron, Predonine, Solu-medorol, Ravonal, Nutrase, Foliamin, Viscorin, Aspara-K, Futraful, Pentcillin, Pansporin, Bestcall, Cefortax, Cefoperazin, Yamatetan, Cefametazone, Shiomarin, Suncefal, Viccilin-S and Zinacef. …
- NAID 110001798481
Related Links
- Zin·a·cef (zĭn′ə-sĕf′) A trademark for the drug cefuroxime. Zinacef, trademark for a cephalosporin antibiotic (cefuroxime sodium). cefuroxime sodium Zinacef Pharmacologic class: Second-generation cephalosporin Therapeutic class: Anti-infective
- Zinacef official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... Zinacef - Clinical Pharmacology After intramuscular (IM) injection of a 750-mg dose of ...
Related Pictures
★リンクテーブル★
[★]
- 英
- cefuroxime CXM
- ラ
- cefuroximum
- 化
- セフロキシムアキセチル cefuroxime axetil、セフロキシムピボキセチル cefuroxime pivoxetil、セフロキシムナトリウム cefuroxime sodium
- 商
- オラセフ、Ceftin, Kefurox, Zinacef
[★]
- 同
- Ceftin, Kefurox, Zinacef
- 関
- Cefuroxime