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Revision as of 14:11, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Latest revision as of 04:10, 2 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Alter: doi. Add: s2cid. 
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{{cs1 config|name-list-style=vanc}}
⚫ {{Drugbox| verifiedrevid = 401949915
{{short description|Chemical to treat chronic bronchitis}}
|
{{Drugbox
⚫ |IUPAC_name = (6''R'',7''R'')-7-(amino) -8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
⚫ | verifiedrevid = 443510665
⚫ | image=Ceftibuten-Formulae.png
⚫ | IUPAC_name = (6''R'',7''R'')-7-(amino)-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
⚫ | width=300
⚫ | image = Ceftibuten.svg
⚫ | width = 200
<!--Clinical data-->
| tradename = Cedax
| Drugs.com = {{drugs.com|monograph|ceftibuten}}
| MedlinePlus = a698023
⚫ | pregnancy_category =
⚫ | legal_status =
⚫ | routes_of_administration =
<!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | metabolism =
⚫ | excretion =
<!--Identifiers-->
⚫ | CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 97519-39-6
⚫ | ATC_prefix = J01
⚫ | ATC_suffix = DD14
⚫ | PubChem = 5282242
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫ | DrugBank = DB01415
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4445419 | ChemSpiderID = 4445419
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IW71N46B4Y | UNII = IW71N46B4Y
⚫ | KEGG_Ref = {{keggcite|correct|kegg}}
| InChI = 1/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
⚫ | KEGG = D00922
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 3510
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 1605
<!--Chemical data-->
⚫ | C=15 | H=14 | N=4 | O=6 | S=2
| smiles = O=C2N1/C(=C\CS12NC(=O)C(=C/CC(=O)O)\c3nc(sc3)N)C(=O)O | smiles = O=C2N1/C(=C\CS12NC(=O)C(=C/CC(=O)O)\c3nc(sc3)N)C(=O)O
| InChIKey = UNJFKXSSGBWRBZ-BJCIPQKHBU
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 1605
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UNJFKXSSGBWRBZ-BJCIPQKHSA-N | StdInChIKey = UNJFKXSSGBWRBZ-BJCIPQKHSA-N
⚫ | CAS_number=97519-39-6
⚫ | ATC_prefix=J01
⚫ | ATC_suffix=DD14
| ATC_supplemental=
⚫ | ChEBI = 3510
⚫ | PubChem=5282242
⚫ | DrugBank=DB01415
⚫ | KEGG = D00922
⚫ | C=15 | H=14 | N=4 | O=6 | S=2
| molecular_weight = 410.427 g.mol<sup>-1</sup>
⚫ | bioavailability=
⚫ | metabolism =
| elimination_half-life=
⚫ | excretion =
⚫ | pregnancy_category =
⚫ | legal_status =
⚫ | routes_of_administration=
}} }}


'''Ceftibuten''' is a third-generation ] ]. It is an orally-administered agent, with 2 dosage forms, capsule or oral suspension. It is marketed by Shionogi USA under the trade name '''Cedax'''. '''Ceftibuten''' is a third-generation ] ].<ref name="Owens_1997">{{cite journal | vauthors = Owens RC, Nightingale CH, Nicolau DP | title = Ceftibuten: an overview | journal = Pharmacotherapy | volume = 17 | issue = 4 | pages = 707–20 | date = 1997 | pmid = 9250548 | doi = 10.1002/j.1875-9114.1997.tb03746.x| s2cid = 32735943 | url = }}</ref><ref name="Guay_1997">{{cite journal | vauthors = Guay DR | title = Ceftibuten: a new expanded-spectrum oral cephalosporin | journal = The Annals of Pharmacotherapy | volume = 31 | issue = 9 | pages = 1022–33 | date = September 1997 | pmid = 9296244 | doi = 10.1177/106002809703100913 | s2cid = 39852306 }}</ref> It is an orally administered agent, with two dosage forms, capsule or oral suspension. It is marketed by ] under the trade name '''Cedax'''.


==Medical uses==
It is active against ], ], ] (K. pneumoniae, K. oxytoca), ], P. mirabils, P. providence, ] sp., ] sp., ] sp. and ] sp.
⚫ {{main article|Cephalosporin}}


Ceftibuten is used to treat acute bacterial ]s of ] (ABECB), acute bacterial ], ], and ]. It is also indicated for ], infections of the ], ], and ].{{Citation needed|date=May 2009}}


==Clinical use== ==Adverse effects==
⚫ In 3,000 patients, ceftibuten was well tolerated. The most frequent reactions were gastrointestinal and nausea.{{cn|date=March 2023}}
⚫ {{main|Cephalosporin}}


===Indications=== ==Susceptibility==
Ceftibuten is used to treat acute bacterial ]s of ] (ABECB), acute bacterial ], ], and ]. It is also indicated for ], infections of the ], ] and ].{{Fact|date=May 2009}} Ceftibuten is active against '']'', '']'', '']'', ''Klebsiella pneumoniae'', ''K. oxytoca'', '']'', ''P. mirabilis'', ''P. providence'', '']'' sp., '']'' sp., '']'' sp., and '']'' sp.{{cn|date=March 2023}}


The following represents ] (MIC) susceptibility data for a few clinically significant microorganisms:
===Adverse reactions===
* ''Haemophilus influenzae'': 0.015–1.0&nbsp;μg/ml
⚫ In studies made in 3,000 patients ceftibuten was well tolerated. Most frequent reactions were gastrointestinal and nauseas.
* ''Moraxella catarrhalis'': 0.5–4.0 &nbsp;μg/ml
* ''Streptococcus pneumoniae'': 0.5–256&nbsp;μg/ml <ref>{{cite web | title = Ceftibuten Susceptibility and Minimum Inhibitory Concentration Range (MIC) Data | url = http://www.toku-e.com/Assets/MIC/Ceftibuten.pdf | date = June 2020 | work = TOKU-E }}</ref>


===Formulations=== ==References==
{{Reflist}}
Ceftibuten is available as capsules containing 400 mg, and a powder for oral suspension containing 90 mg per 5 ml.


==External links== ==External links==
* *
* *


{{CephalosporinAntiBiotics}} {{CephalosporinAntiBiotics}}
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