ceftin

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% on an empty stomach, up to 52% if taken after food
Half-life	80 minutes
Excretion	Urine 66–100% unchanged
Identifiers
CAS number	55268-75-2
ATC code	J01DC02 S01AA27 QJ51DC02
PubChem	CID 5361202
DrugBank	DB01112
ChemSpider	4514699
UNII	O1R9FJ93ED
KEGG	D00262
ChEMBL	CHEMBL466
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 ; Key:JFPVXVDWJQMJEE-SWWZKJRFSA-N ;
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同: Ceftin, Kefurox, Zinacef
関: Cefuroxime

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/08 21:56:57」(JST)

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[Wiki en表示]

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.^[1] The generic form of cefuroxime is also called ceftin. The patent for this antibiotic has now expired in the United States.

In the United States, this antibiotic is also sold as Zinacef by Covis Pharmaceuticals.^[2] In India, it is sold as Supacef by GSK.^[3]

Cefuroxime axetil is an acetoxyetyl-ester-prodrug of cefuroxime which is effective orally.^[4] In Bangladesh, this drug is available as Xorimax by Sandoz and 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 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.^[5]

References

^ "Cefuroxime medical facts from". Drugs.com.
^ http://www.covispharma.ch/assets/pdf/covis-pharma-acquires-portfolio-of-drugs-from-glaxosmithkline.pdf
^ "GlaxoSmithKline Pharmaceuticals.Prescription Medicines – Anti-Infective". Gsk-india.com. 26 March 2013.
^ 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.

UpToDate Contents

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English Journal

Design and characterization of cefuroxime axetil biphasic floating minitablets.

Jammula S, Patra CN, Swain S, Panigrahi KC, Nayak S, Dinda SC, Rao ME.Author information Department of Pharmaceutics, Roland Institute of Pharmaceutical Sciences , Berhampur, Odisha , India .AbstractAbstract Biphasic floating minitablets of cefuroxime axetil were prepared by melt granulation technique using two different grades of gelucire namely 50/13 and 43/01 to maintain constant plasma drug concentration. Loading dose of cefuroxime axetil was formulated as immediate release (IR) minitablets by using hydrophilic grade of gelucire 50/13. Maintenance dose was formulated as floating sustained release (SR) minitablets by using hydrophobic grade of gelucire 43/01. The prepared IR and SR granules were subjected to micromeritic studies and scanning electron microscopy. Fourier transform infrared spectroscopy (FT-IR) study revealed that drug and selected carriers were compatible. In vitro dissolution study of optimized IR minitablets showed more than 85% of loading dose dissolved within 30 min. Optimized SR minitablets showed zero lag time with floating duration more than 12 h. The drug release from SR minitablets was linear with square root of time with non-Fickian diffusion-controlled release. The optimized batch of minitablets was filled into 0 size hard gelatin capsule. In vitro dissolution study for capsule showed an immediate burst release followed by SR up to 12 h. There is no significant change in dissolution data after storage at 40 °C and 75% RH for three months. Microbiological assay of dissolution samples of optimized minitablets filled in capsules showed proportionate increase in inhibition of growth against Escherichia coli up to 12 h samples. In vivo bioavailability study in albino rabbits showed three times improvement in oral bioavailability.
Drug delivery.Drug Deliv.2014 Jan 13. [Epub ahead of print]
Abstract Biphasic floating minitablets of cefuroxime axetil were prepared by melt granulation technique using two different grades of gelucire namely 50/13 and 43/01 to maintain constant plasma drug concentration. Loading dose of cefuroxime axetil was formulated as immediate release (IR) minitablets
PMID 24417642

In vitro/in vivo comparison of cefuroxime release from poly(ε-caprolactone)-calcium sulfate implants for osteomyelitis treatment.

Yaprakci V, Erdemli O, Kayabolen A, Tezcaner A, Bozkurt F, Keskin D.Author information Department of Veterinary Medicine, Afyon Kocatepe University, Afyon, Turkey.AbstractThis study aimed to investigate the release of cefuroxime axetil (CF) and calcium from poly(ε-caprolactone) (PCL)-calcium sulfate (CaS) implants (PCL:CaS 2:1-10% CF; PCL:CaS 2:1-20% CF; PCL:CaS 1:1-10% CF) for treating infectious bone diseases. Bioactivity, crystallinity and strength, and release profiles under standard and pressurized release conditions were studied. PCL:CaS 2:1-20% CF had slower release than 10% loading. These groups had no significant change in CF and Ca release in response to pressure. The PCL:CaS 1:1 group had the slowest release despite having higher CaS, probably due to more compaction of discs. In contrast, pressure caused significant differentiation of CF and Ca(2+) release. The presence of CaS enhanced mechanical properties and bioactivity of discs. SEM and XPS results showed calcium-phosphate containing accumulations on surfaces upon SBF incubation. CF-loaded implants were applied in a rabbit osteomyelitis model. In vivo CF release was enhanced with increased CaS proportions, suggesting that in vivo release conditions are closer to pressurized in vitro conditions. In the control group, there was still some inflammation in the bone and no complete coverage with bone was achieved in the defect site. Discs provided a suitable surface for regeneration of bone. However, bone formation in the PCL:CaS 1:1 disc implanted group was more complete and regular than in the 2:1 group.
Biotechnology and applied biochemistry.Biotechnol Appl Biochem.2013 Nov-Dec;60(6):603-16. doi: 10.1002/bab.1118. Epub 2013 Aug 26.
This study aimed to investigate the release of cefuroxime axetil (CF) and calcium from poly(ε-caprolactone) (PCL)-calcium sulfate (CaS) implants (PCL:CaS 2:1-10% CF; PCL:CaS 2:1-20% CF; PCL:CaS 1:1-10% CF) for treating infectious bone diseases. Bioactivity, crystallinity and strength, and release p
PMID 23586705

Fosfomycin trometamol: a review of its use as a single-dose oral treatment for patients with acute lower urinary tract infections and pregnant women with asymptomatic bacteriuria.

Keating GM.Author information Adis, 41 Centorian Drive, Private Bag 65901, Mairangi Bay, North Shore, 0754, Auckland, New Zealand, demail@springer.com.AbstractFosfomycin trometamol (fosfomycin tromethamine) [Monuril(®), Monurol(®), Monural(®)] is approved in numerous countries worldwide, mainly for the treatment of uncomplicated urinary tract infections (UTIs). Fosfomycin has good in vitro activity against common uropathogens, such as Escherichia coli (including extended-spectrum β-lactamase-producing E. coli), Proteus mirabilis, Klebsiella pneumoniae and Staphylococcus saprophyticus, and the susceptibility of uropathogens to fosfomycin has remained relatively stable over time. A single oral dose of fosfomycin trometamol 3 g (the approved dosage) achieves high concentrations in urine. Results of recent randomized trials indicate that single-dose fosfomycin trometamol had similar clinical and/or bacteriological efficacy to 3- to 7-day regimens of ciprofloxacin, norfloxacin, cotrimoxazole or nitrofurantoin in women with uncomplicated lower UTIs. In addition, single-dose fosfomycin trometamol had similar bacteriological efficacy to a 5-day course of cefuroxime axetil or a 7-day course of amoxicillin/clavulanic acid in pregnant women with asymptomatic bacteriuria, and similar clinical and/or bacteriological efficacy to a 5-day course of cefuroxime axetil or amoxicillin/clavulanic acid or a 3-day course of ceftibuten in pregnant women with a lower UTI. Single-dose fosfomycin trometamol was generally well tolerated, with gastrointestinal adverse events (e.g. diarrhoea, nausea) reported most commonly. In conclusion, single-dose fosfomycin trometamol is an important option for the first-line empirical treatment of uncomplicated lower UTIs.
Drugs.Drugs.2013 Nov;73(17):1951-66. doi: 10.1007/s40265-013-0143-y.
Fosfomycin trometamol (fosfomycin tromethamine) [Monuril(®), Monurol(®), Monural(®)] is approved in numerous countries worldwide, mainly for the treatment of uncomplicated urinary tract infections (UTIs). Fosfomycin has good in vitro activity against common uropathogens, such as Escherichia coli
PMID 24202878

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[1] "Cefuroxime medical facts from". Drugs.com.

[2] ttp://www.covispharma.ch/assets/pdf/covis-pharma-acquires-portfolio-of-drugs-from-glaxosmithkline.pdf

[3] "GlaxoSmithKline Pharmaceuticals.Prescription Medicines – Anti-Infective". Gsk-india.com. 26 March 2013.

[4] Walter Sneader. "Drug Discovery: History".

[pmid16451776-5] Pichichero ME (2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of family practice 55 (2): 106–12. PMID 16451776.

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