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)』「2013/04/12 15:17:59」(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 |
Clinical data |
Trade names |
Ceftin, Zinacef |
MedlinePlus |
a601206 |
Pregnancy cat. |
Not known to be harmful (BNF) |
Legal status |
Prescription Only Medicine |
Routes |
intramuscular, intravenous |
Pharmacokinetic data |
Bioavailability |
37% on empty stomach, up to 52% if taken after food |
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 |
ChemSpider |
4514699 Y |
UNII |
O1R9FJ93ED Y |
KEGG |
D00262 Y |
ChEMBL |
CHEMBL466 Y |
Chemical data |
Formula |
C16H16N4O8S |
Mol. mass |
424.386 g/mol |
SMILES
- 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
-
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
Key:JFPVXVDWJQMJEE-SWWZKJRFSA-N Y
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Y (what is this?) (verify)
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Cefuroxime is an oral and parenteral second generation cephalosporin antibiotic. It was discovered by Glaxo now GlaxoSmithKline and introduced in 1978 as Zinacef.[1] It was approved by FDA on Oct 19, 1983.[2] In US it is available as Zinacef by Covis Pharmaceuticals as the company acquired the US rights of the product from GSK.[3] In India it is available as Supacef by GSK.[4] Cefuroxime axetil is an acetoxyetyl ester prodrug of cefuroxime which is effective orally.[5]
Indications
As for the other cephalosporins, although as a second-generation it is less susceptible to beta-lactamase and so may have greater activity against Haemophilus influenzae, Neisseria gonorrhoeae and Lyme disease. Unlike other second generation cephalosporins, cefuroxime can cross the blood-brain-barrier.
Side effects
Cefuroxime is generally well tolerated and side effects are usually transient. Cefuroxime, if ingested after food, 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 there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, recent assessments have shown no increased risk for cross-allergy for cefuroxime and several other 2nd generation or later cephalosporins.[6]
References
- ^ http://www.gsk.com/about/history.htm
- ^ http://www.drugs.com/mtm/cefuroxime.html
- ^ http://www.covispharma.ch/assets/pdf/covis-pharma-acquires-portfolio-of-drugs-from-glaxosmithkline.pdf,
- ^ http://www.gsk-india.com/product-antiinfective.html
- ^ http://books.google.co.in/books?id=Cb6BOkj9fK4C&pg=PA326&lpg=PA326&dq=discovery+of+cefuroxime+axetil&source=bl&ots=NNaeE7Ai9Y&sig=m3WYseJk5-5vzxK0QCyHsYnHw0w&hl=en&sa=X&ei=SftcT5TfCIOnrAeNpO2VCQ&ved=0CE4Q6AEwBg#v=onepage&q=discovery%20of%20cefuroxime%20axetil&f=false
- ^ Pichichero ME (2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of family practice 55 (2): 106–12. PMID 16451776.
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) |
Penicillins
(penams)
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Extended sp.
|
- 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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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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|
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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
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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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GlaxoSmithKline
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Subsidiaries |
- GlaxoSmithKline Pakistan
- GlaxoSmithKline Pharmaceuticals Ltd
- Stiefel Laboratories
- ViiV Healthcare (85%)
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Predecessors and fully
integrated acquisitions |
- Allen & Hanburys
- Beecham Group
- Block Drug
- Burroughs Wellcome
- Glaxo
- Glaxo Wellcome
- Human Genome Sciences
- Recherche et Industrie Thérapeutiques
- SmithKline Beecham
- Smith, Kline & French
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|
Products
(List) |
Current
|
Pharmaceuticals
|
- Advair
- Albenza
- Alli
- Amerge
- Amoxil
- Arixtra
- Arranon/Atriance
- Augmentin
- Avamys/Veramyst
- Avandia
- Avodart
- AZT1
- Beconase
- Boniva
- Ceftin
- Combivir1
- Coreg
- Dexedrine
- Dyazide
- Epivir/Epivir-HBV/Heptovir/Zeffix1
- Flixonase
- Imitrex/Treximet
- Jayln
- Lamictal
- Lanoxin
- Levitra2
- Lovaza
- Parnate
- Paxil/Seroxat/Aropax
- Promacta
- Relenza
- Requip
- Rescriptor1
- Serlipet
- Tagamet
- Treximet
- Trizivir1
- Tykerb/Tyverb
- Valtrex/Zelitrex
- Ventolin HFA
- Viracept1
- Wellbutrin
- Zantac
- Ziagen1
- Zofran
- Zovirax
|
|
Vaccines
|
- Hepatyrix
- Pandemrix
- Twinrix
|
|
Other
|
- Aquafresh
- Boost
- Eno
- Horlicks
- Lucozade
- Maxinutrition
- Nicoderm
- Nicorette
- NiQuitin
- Panadol
- Panadol night
- Ralgex
- Ribena
- Sensodyne
- Solpadeine
- Synthol
- Tums
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|
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Former
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- BC Powder
- Geritol
- Goody's Powder
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|
|
People |
Current directors
|
- Chris Gent
- Andrew Witty
- Roy Anderson
- Stephanie Burns
- Stacey Cartwright
- Lawrence Culp
- Crispin Davis
- Simon Dingemans
- Judy Lewent
- Deryck Maughan
- James Murdoch
- Daniel Podolsky
- Moncef Slaoui
- Tom de Swaan
- Robert Wilson
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Other
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- Thomas Beecham
- Silas M. Burroughs
- Mahlon Kline
- John K. Smith
- Henry Wellcome
|
|
|
Other |
- Canada v. GlaxoSmithKline Inc.
- GlaxoSmithKline Prize
- Side Effects
- United States v. GlaxoSmithKline
|
|
- 1Products of ViiV Healthcare 2Co-marketed with Bayer Pharmaceuticals
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|
UpToDate Contents
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English Journal
- Uveitis attack and drug reaction due to cefuroxime axetil.
- Akman C1, Duran A2, Kalafat UM1, Ocak T2.
- Cutaneous and ocular toxicology.Cutan Ocul Toxicol.2016 Sep;35(3):254-6. doi: 10.3109/15569527.2015.1067817. Epub 2015 Jul 23.
- Antibiotics are natural or synthetic substances that are used to control bacterial infections because antibiotics are by definition only effective against bacteria. A 30-year-old female came to our emergency clinic complaining rubor in both eyes, especially in the left eye, with swelling, rubor and
- PMID 26203731
- [Lyme disease--clinical manifestations and treatment].
- Stock I.
- Medizinische Monatsschrift für Pharmazeuten.Med Monatsschr Pharm.2016 May;39(5):197-204; quiz 205-6.
- Lyme disease (Lyme borreliosis) is a systemic infectious disease that can present in a variety of clinical manifestations. The disease is caused by a group of spirochaetes--Borrelia burgdorferi sensu lato or Lyme borrelia--that are transmitted to humans by the bite of Ixodes ticks. Lyme disease is t
- PMID 27348896
- Diagnosis, Treatment, and Prevention of Lyme Disease, Human Granulocytic Anaplasmosis, and Babesiosis: A Review.
- Sanchez E1, Vannier E1, Wormser GP2, Hu LT3.
- JAMA.JAMA.2016 Apr 26;315(16):1767-77. doi: 10.1001/jama.2016.2884.
- IMPORTANCE: Lyme disease, human granulocytic anaplasmosis (HGA), and babesiosis are emerging tick-borne infections.OBJECTIVE: To provide an update on diagnosis, treatment, and prevention of tick-borne infections.EVIDENCE REVIEW: Search of PubMed and Scopus for articles on diagnosis, treatment, and p
- PMID 27115378
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- オラセフ、Ceftin, Kefurox, Zinacef
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