セフチブテン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/06 07:46:38」(JST)
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Ceftibuten
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| Systematic (IUPAC) name |
| (6R,7R)-7-([(Z)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino) -8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Clinical data |
| Trade names |
Cedax |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a698023 |
| Pregnancy cat. |
? |
| Legal status |
? |
| Identifiers |
| CAS number |
97519-39-6 Y |
| ATC code |
J01DD14 |
| PubChem |
CID 5282242 |
| DrugBank |
DB01415 |
| ChemSpider |
4445419 Y |
| UNII |
IW71N46B4Y Y |
| KEGG |
D00922 Y |
| ChEBI |
CHEBI:3510 Y |
| ChEMBL |
CHEMBL1605 Y |
| Chemical data |
| Formula |
C15H14N4O6S2 |
| Mol. mass |
410.427 g.mol-1 |
SMILES
- O=C2N1/C(=C\CS[C@@H]1[C@@H]2NC(=O)C(=C/CC(=O)O)\c3nc(sc3)N)C(=O)O
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InChI
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InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1 Y
Key:UNJFKXSSGBWRBZ-BJCIPQKHSA-N Y
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Y (what is this?) (verify)
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Ceftibuten is a third-generation cephalosporin antibiotic. It is an orally-administered agent, with 2 dosage forms, capsule or oral suspension. It is marketed by Pernix Therapeutics under the trade name Cedax.
It is active against Haemophilus influenzae, Moraxella catarrhalis, Escherichia coli (K. pneumoniae, K. oxytoca), Proteus vulgaris, P. mirabils, P. providence, Salmonella sp., Shigella sp., Enterobacter sp. and Streptococcus sp.
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Contents
- 1 Clinical use
- 1.1 Indications
- 1.2 Adverse reactions
- 1.3 Formulations
- 2 External links
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Clinical use
Main article: Cephalosporin
Indications
Ceftibuten is used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis. It is also indicated for pneumonia, infections of the urinary tract, enteritis and gastroenteritis.[citation needed]
Adverse reactions
In studies made in 3,000 patients ceftibuten was well tolerated. Most frequent reactions were gastrointestinal and nauseas.
Formulations
Ceftibuten is available as capsules containing 400 mg, and a powder for oral suspension containing 180 mg per 5 ml.
External links
- Manufacturer's website
- Drug information from RxList
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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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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
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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
- In vitro activity of beta-lactam antibiotics against CTX-M-producing Escherichia coli.
- Tärnberg M, Ostholm-Balkhed A, Monstein HJ, Hällgren A, Hanberger H, Nilsson LE.SourceDepartment of Clinical and Experimental Medicine, Faculty of Health Sciences, Linköping University, 581 85, Linköping, Sweden. maria.tarnberg@liu.se
- European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology.Eur J Clin Microbiol Infect Dis.2011 Aug;30(8):981-7. Epub 2011 Feb 6.
- Beta-lactam antibiotics have been discussed as options for the treatment of infections caused by multiresistant extended-spectrum beta-lactamase (ESBL)-producing bacteria if the minimum inhibitory concentration (MIC) is low. The objective of this study was to investigate the in vitro activity of dif
- PMID 21298459
- Strategies to overcome extended-spectrum β-lactamases (ESBLs) and AmpC β-lactamases in shigellae.
- Livermore DM, Mushtaq S, Nguyen T, Warner M.SourceAntibiotic Resistance Monitoring & Reference Laboratory, Health Protection Agency Microbiology Services-Colindale, 61 Colindale Avenue, London NW9 5EQ, UK. david.livermore@hpa.org.uk
- International journal of antimicrobial agents.Int J Antimicrob Agents.2011 May;37(5):405-9. Epub 2011 Jan 26.
- Oral cephalosporins and mecillinam are used to treat Shigella infections, but are compromised by extended-spectrum β-lactamases (ESBLs) and plasmid AmpC β-lactamases. Potential solutions include combining an oral or intravenous cephalosporin with a β-lactamase inhibitor (BLI) or using an oral pen
- PMID 21276715
- Evidence-based treatment limitations prevent any therapeutic recommendation for acute poststreptococcal glomerulonephritis in children.
- Zaffanello M, Cataldi L, Franchini M, Fanos V.SourceDepartment of Mother-Child and Biology-Genetics, University of Verona, 37134 Verona, Italy. marco.zaffanello@univr.it
- Medical science monitor : international medical journal of experimental and clinical research.Med Sci Monit.2010 Apr;16(4):RA79-84.
- The majority of children with the epidemic form of acute post-streptococcal glomerulonephritis (APSGN) have an excellent prognosis, which contrasts with the poor long-term outcome of sporadic cases. Therapy is largely supportive. Rarely, the disease shows long-term complications, worsening to chroni
- PMID 20357732
Related Links
- Learn about the prescription medication Cedax (Ceftibuten), drug uses, dosage, side effects, drug interactions, warnings, reviews and patient labeling. ... What are the possible side effects of ceftibuten (Cedax)? Get emergency ...
- Pediatric patients weighing more than 45 kg should receive the maximum daily dose of 400 mg. Renal Impairment CEDAX (ceftibuten) Capsules and CEDAX (ceftibuten) Oral Suspension may be administered at normal doses in the ...
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- 英
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- セフテム、Cedax
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