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)』「2016/06/30 22:54:38」(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
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Clinical data |
Trade names |
Cedax |
AHFS/Drugs.com |
Monograph |
MedlinePlus |
a698023 |
Identifiers |
CAS Number |
97519-39-6 Y |
ATC code |
J01DD14 (WHO) |
PubChem |
CID 5282242 |
DrugBank |
DB01415 Y |
ChemSpider |
4445419 Y |
UNII |
IW71N46B4Y Y |
KEGG |
D00922 Y |
ChEBI |
CHEBI:3510 Y |
ChEMBL |
CHEMBL1605 Y |
Chemical data |
Formula |
C15H14N4O6S2 |
Molar mass |
410.427 g.mol−1 |
SMILES
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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
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Key:UNJFKXSSGBWRBZ-BJCIPQKHSA-N Y
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(verify) |
Ceftibuten is a third-generation cephalosporin antibiotic. It is an orally administered agent, with two dosage forms, capsule or oral suspension. It is marketed by Pernix Therapeutics under the trade name Cedax.
Contents
- 1 Clinical use
- 1.1 Indications
- 1.2 Adverse reactions
- 1.3 Formulations
- 2 Spectrum of susceptibility
- 3 References
- 4 External links
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 3,000 patients, ceftibuten was well tolerated. The 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.
Spectrum of susceptibility
Ceftibuten is active against Haemophilus influenzae, Moraxella catarrhalis, Escherichia coli, Klebsiella pneumoniae, K. oxytoca, Proteus vulgaris, P. mirabilis, P. providence, Salmonella sp., Shigella sp., Enterobacter sp., and Streptococcus sp.
The following represents minimum inhibitory concentration (MIC) susceptibility data for a few clinically significant microorganisms:
- Haemophilus influenzae: 0.015–1.0 µg/ml
- Moraxella catarrhalis: 0.5–4.0 µg/ml
- Streptococcus pneumoniae: 0.5–256 µg/ml [1]
References
- ^ http://www.toku-e.com/Assets/MIC/Ceftibuten.pdf
External links
- Manufacturer's website
- Drug information from RxList
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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Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- Pediatric Round Pneumonia.
- Liu YL, Wu PS, Tsai LP, Tsai WH.SourceDepartment of Pediatrics, Buddhist Tzu Chi General Hospital, Taipei Branch, Xindian, New Taipei, Taiwan; Degree Program of Translational Medicine, Academia Sinica-National Taiwan University, Taipei, Taiwan.
- Pediatrics and neonatology.Pediatr Neonatol.2013 Mar 13. pii: S1875-9572(13)00015-6. doi: 10.1016/j.pedneo.2013.01.014. [Epub ahead of print]
- "Round pneumonia," or "spherical pneumonia," is a well-characterized clinical entity that seems to be less addressed by pediatricians in Taiwan. We herein report the case of a 7-year-old boy who presented with prolonged fever, cough, and chest X-rays showing a well-demarcated round mass measuring 5.
- PMID 23597522
- [Preventive antibacterial treatment in oral bone augmentation procedures.]
- Chuvilkin VI, Chuvilkina EI, Tsarev VN, Shirokov IE.SourceMoskovskiĭ gosudarstvennyĭ mediko-stomatologicheskiĭ universitet Minzdrava Rossii.
- Stomatologiia.Stomatologiia (Mosk).2013;92(3):84-87.
- The paper contains clinical and microbiological base for the use of Ceftibuten for prevention of inflammatory complications after bone augmentation and dental implant placement.
- PMID 23752848
- Surveillance of gonococcal antimicrobial susceptibility resulting in early detection of emerging resistance.
- Lo JY, Ho KM, Lo AC.SourcePublic Health Laboratory Services Branch, Centre for Health Protection, Department of Health, Hong Kong Special Administrative Region, China. janicelo@dh.gov.hk
- The Journal of antimicrobial chemotherapy.J Antimicrob Chemother.2012 Jun;67(6):1422-6. doi: 10.1093/jac/dks036. Epub 2012 Feb 14.
- OBJECTIVES: To undertake laboratory and clinical surveillance of gonococcal antimicrobial susceptibility to various therapeutic agents in Hong Kong, so as to monitor for emerging resistance and to inform on appropriate choice of empirical therapy.METHODS: Trends in susceptibility of gonococci to cef
- PMID 22334602
Japanese Journal
- ラットにおけるペプチドトランスポータを介するβ-ラクタム抗生物質セフチブテンの吸収に及ぼす亜鉛の阻害効果
- OKAMURA Miyako,TERADA Tomohiro,KATSURA Toshiya,INUI Ken-ichi
- Drug metabolism and pharmacokinetics 23(6), 464-468, 2008-12-25
- NAID 10025722201
- Purification by p-aminobenzoic acid (PABA)-affinity chromatography and the functional reconstitution of the nateglinide/H+ cotransport system in the rat intestinal brush-border membrane
- Saito Yoshitaka,Itagaki Shirou,Kubo Sayaka,Kobayashi Masaki,Hirano Takeshi,Iseki Ken
- Biochemical and Biophysical Research Communications 340(3), 879-886, 2006-02-17
- … Recently, we have shown that nateglinide transport occurs via the ceftibuten/H+ cotransport system, which is distinct from PepT1, and that the fluorescein/H+ cotransport system is involved in the uptake of nateglinide. … In the first part of this study, we demonstrated that the ceftibuten/H+ cotransport system is identical to the fluorescein/H+ cotransport system. … We demonstrated that nateglinide, ceftibuten, and fluorescein are transported by the same transporter in the intestine. …
- NAID 120000958068
- ANTIBIOTIC PROPHYLAXIS FOR TRANSRECTAL NEEDLE BIOPSY OF THE PROSTATE
- OYAMA NOBUO,MOMOSE HITOSHI
- Journal of Nara Medical Association 56(1), 31-36, 2005-02-28
- … In the first 30 cases constituting Group 1, ceftibuten (CETB) was administered orally at 200 mg b.i.d. …
- NAID 110004599230
Related Links
- Ceftibuten [CETB] セフチブテン, セフェム系 1. 商品名 先発品 セフテムカプセル100mg/セフテムカプセル200mg 【塩野義製薬】 2. 日本における発売年 1992(平成4)年 3. 特長 インフルエンザ菌,大腸菌等のグラム陰性菌に対し抗菌 力 ...
- Keep all appointments with your doctor and the laboratory. Your doctor will order certain lab tests to check your response to ceftibuten. If you are diabetic, use Clinistix or TesTape (not Clinitest) to test your urine for sugar ...
Related Pictures
★リンクテーブル★
[★]
- 英
- cephalosporin antibiotics, cephalosporin, cephalosporins
- 同
- セフェム系抗菌薬?、セフェム系抗生物質? cephem antibiotic? cephem antibiotics
- 関
- 抗菌薬、βラクタム系抗菌薬 、第三世代抗生物質
特徴
- グラム陽性菌、グラム陰性菌
構造
副作用
- 過敏症(ペニシリン系抗菌薬と同様であるが、頻度はペニシリン系に比べ低い)
- (1)ジスルフィラム様作用、(2)ビタミンK依存性の凝固因子の産生低下(cefotetanとcefoperazoneに特徴的。共通点はN-methylthiotetrazole(NMTT) side chainを持つこと)。(PPC.612)
セフェム系抗菌薬
[★]
- 同
- 第3世代セフェム、第三世代抗生物質 antibiotics of third generation、第三世代セフェム系抗生物質 cephem antibiotics of third generation、第3世代セファロスポリン
- 関
- セファロスポリン系抗菌薬
特徴
- 第3世代セフェム以上は口腔内嫌気性細菌をカバーできる ・・・ わざわざABPC/SBTを選択しなくて良い。
第三世代セフェム
[★]
- 英
- ceftibuten
- 商
- セフテム、Cedax
- 関
- 第三世代セフェム、セファロスポリン系抗菌薬