zinacef

同

Ceftin, Kefurox, Zinacef

関

Cefuroxime

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/14 01:31:26」(JST)

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Cefuroxime

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	Zinacef,TURBOCEF
MedlinePlus	a601206
Pregnancy cat.	B
Legal status	RX only
Routes	intramuscular, intravenous, oral
Pharmacokinetic data
Bioavailability	37 percent on empty stomach, up to 52 percent if taken after food
Half-life	80 minutes
Excretion	Urine 66–100 percent 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
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
Y (what is this?)  (verify)

Cefuroxime is a parenteral or oral second-generation cephalosporin antibiotic. This antibiotic was discovered by the Glaxo company, now GlaxoSmithKline, and it was first marketed in 1978 as Zinacef. Zinacef was approved by the U.S. Food and Drug Administration on Oct 19, 1983. The generic form of cefuroxime is also called "Ceftin". The 17-year patent for this antibiotic has now expired in the United States, hence the patent "rights" to produce this medication are now irrelevant.

In the United States this antibiotic is also sold as "Zinacef" by Covis Pharmaceuticals. In India, this antibiotic is sold as Supacef by GSK.

Cefuroxime axetil is an acetoxyetyl-ester-prodrug of cefuroxime which is effective orally. In Bangladesh, this drug is available as Xorimax by Sandoz, Turbocef by Beximco Pharmaceuticals Limited.

Indications

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 there is a widely-stated crossallergic risk of about 10 percent between cephalosporins and penicillin, recent assessments have shown no increased risk for a crossallergic reaction for cefuroxime and several other second-generation or later cephalosporins.

References

UpToDate Contents

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• 1. セフェム系 cephalosporins
• 2. ライム病の治療 treatment of lyme disease
• 3. 小児における急性中耳炎：治療 acute otitis media in children treatment
• 4. 侵襲性肺炎球菌（Streptococcus pneumoniae）感染症および菌血症 invasive pneumococcal streptococcus pneumoniae infections and bacteremia
• 5. Borrelia miyamotoi感染症 borrelia miyamotoi infection

English Journal

• Design, synthesis and biological evaluation of 4-benzoyl-1-dichlorobenzoylthiosemicarbazides as potent Gram-positive antibacterial agents.

• Paneth A1, Plech T1, Kaproń B1, Hagel D1, Kosikowska U2, Kuśmierz E1, Dzitko K3, Paneth P4.
• Journal of enzyme inhibition and medicinal chemistry.J Enzyme Inhib Med Chem.2016 Jun;31(3):434-40. doi: 10.3109/14756366.2015.1036050. Epub 2015 Apr 21.
• Twelve 4-benzoyl-1-dichlorobenzoylthiosemicarbazides have been tested as potential antibacterials. All the compounds had MICs between 0.49 and 15.63 µg/ml toward Micrococcus luteus, Bacillus cereus, Bacillus subtilis and Staphylococcus epidermidis indicating, in most cases, equipotent or even mor
• PMID 25897586

• Effectiveness and Safety of an Intracameral Injection of Cefuroxime for the Prevention of Endophthalmitis After Cataract Surgery With or Without Perioperative Capsular Rupture.

• Daien V1, Papinaud L2, Gillies MC3, Domerg C2, Nagot N4, Lacombe S5, Daures JP5, Carriere I6, Villain M7.
• JAMA ophthalmology.JAMA Ophthalmol.2016 May 2. doi: 10.1001/jamaophthalmol.2016.1351. [Epub ahead of print]
• Importance: Postoperative endophthalmitis (POE) often results in severe visual impairment. In clinical studies, an intracameral cefuroxime injection at the end of surgery was found to be effective at reducing the incidence of POE. Two important issues are the retinal safety of cefuroxime and its use
• PMID 27136069

• The influence of uncertainty and location-specific conditions on the environmental prioritisation of human pharmaceuticals in Europe.

• Oldenkamp R1, Huijbregts MA2, Ragas AM3.
• Environment international.Environ Int.2016 May;91:301-11. doi: 10.1016/j.envint.2016.01.025. Epub 2016 Mar 19.
• The selection of priority APIs (Active Pharmaceutical Ingredients) can benefit from a spatially explicit approach, since an API might exceed the threshold of environmental concern in one location, while staying below that same threshold in another. However, such a spatially explicit approach is rela
• PMID 26999515

Japanese Journal

• ドプラム注射薬の配合変化試験に関する研究

• 病院薬学 13(4), 244-260, 1987-08-20
• NAID 110001798481

• ドプラム注射薬の配合変化試験に関する研究

• 病院薬学 13(4), 244-260, 1987
• NAID 130004299018

Related Links

• Zinacef - FDA prescribing information, side effects and uses

Zinacef official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... Cefuroxime is approximately 50% bound to serum protein. Microbiology Mechanism of ...

• Zinacef: Indications, Side Effects, Warnings - Drugs.com

Easy to read patient leaflet for Zinacef. Includes indications, proper use, special instructions, precautions, and possible side effects. ... If OVERDOSE is suspected: Contact 1-800-222-1222 (the American Association of Poison ...

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