セフブペラゾン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/05/15 10:16:22」(JST)
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Cefbuperazone
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Systematic (IUPAC) name |
(6R,7S)-7-([(2R,3S)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-3-hydroxybutanoyl]amino)-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
℞ Prescription only |
Routes |
IM, IV |
Identifiers |
CAS number |
76610-84-9 Y |
ATC code |
J01DC13 |
PubChem |
CID 127527 |
ChemSpider |
26355342 N |
UNII |
T0785J3X40 Y |
KEGG |
D03423 Y |
Chemical data |
Formula |
C22H29N9O9S2 |
Mol. mass |
627.65 g/mol |
SMILES
- CCN1CCN(C(=O)C1=O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]2([C@@H]3N(C2=O)C(=C(CS3)CSc4nnnn4C)C(=O)O)O
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InChI
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InChI=1S/C21H27N9O9S2/c1-4-28-5-6-29(15(34)14(28)33)19(38)22-11(9(2)31)13(32)23-21(39)17(37)30-12(16(35)36)10(7-40-18(21)30)8-41-20-24-25-26-27(20)3/h9,11,18,31,39H,4-8H2,1-3H3,(H,22,38)(H,23,32)(H,35,36)/t9-,11+,18+,21-/m0/s1 N
Key:RMYHXMFWMQQUSC-FATMUFLPSA-N N
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N (what is this?) (verify) |
Cefbuperazone (INN) is a second-generation cephalosporin antibiotic.[1][2]
References
- ^ Izumi, K.; Kawazoe, K.; Mikamo, H.; Ito, K.; Tamaya, T. (1995). "In vivo bacterial regrowth-inhibition effect of cefbuperazone and amikacin in puerperal uterine cavity". Journal of chemotherapy (Florence, Italy). 7 Suppl 4: 173–176. PMID 8904147. edit
- ^ US 4754030 "Cefbuperazone crystalline triethylamine salt"
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) |
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
- Isoniazid
|
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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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English Journal
- Pharmacokinetic profile of cefbuperazone in healthy Chinese volunteers after single and multiple drip intravenous infusion by HPLC-MS/MS.
- Liu D1, Geng T1, Wang Y2, Ding L3.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2016 Sep 10;129:28-33. doi: 10.1016/j.jpba.2016.06.029. Epub 2016 Jun 23.
- A selective and reproducible HPLC-MS/MS method was developed and fully validated for the determination of cefbuperazone in human plasma and urine. Samples were prepared using protein precipitation and separated on a Zorbax Eclipse Plus C18 column (2.1×50mm, 3.5μm). The API-4000 mass spectrometer w
- PMID 27394175
- Suspected Anaphylactic Reaction Prior to Induction of Anesthesia.
- Lee KH1, Lim HK1, Park JH1, Do HJ1, Jeon YG1.
- Journal of lifestyle medicine.J Lifestyle Med.2015 Mar;5(1):26-9. doi: 10.15280/jlm.2015.5.1.26. Epub 2015 Mar 30.
- Although uncommon, anaphylactic reactions during surgery are very dangerous and can result in serious morbidity. Various anesthetics can trigger anaphylactic reactions, and incidents with cephalosporin antibiotics are on the rise. In the case presented, an 84-year-old woman scheduled for calcaneus f
- PMID 26528427
- (2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonyl-amino]-3-hydroxy-butyric acid monohydrate.
- Ji CX, Cui YT, Yang DL, Guo C.
- Acta crystallographica. Section E, Structure reports online.Acta Crystallogr Sect E Struct Rep Online.2008 Jun 19;64(Pt 7):o1292. doi: 10.1107/S1600536808017832.
- In the title compound, C(11)H(17)N(3)O(6)·H(2)O, an important building block of the medicine cefbuperazone sodium, the piperazine ring adopts a screw-boat conformation. Inter-molecular O-H⋯O and intra-molecular N-H⋯O hydrogen bonds are observed. The water mol-ecule participates as both donor an
- PMID 21202922
Japanese Journal
- Effects of antineoplastics, antibiotics and antidiabetics on acetaldehyde metabolism after alcohol ingestion.
- Kan Shin,Moriya Fumio,Ishizu Hideo
- Acta Medica Okayama 52(1), 1998-02
- … Furthermore, daily administration of cephem antibiotics containing the MTT group, latamoxef, cefamandole, cefoperazone and cefbuperazone, significantly increased blood acetaldehyde concentrations. …
- NAID 120002312418
- Prevotella intermedia MA 1とMA 1-V 2由来β-lactamaseの基質特異性
- 船岡 勝博
- 歯科医学 60(3), g1-g2, 1997-09-25
- … このうち阻害効果が検出された抗菌薬は4種 (cefoxitin, cefmetazole, cefbuperazoneおよびlatamoxef)で, 残り5抗菌薬では阻害効果はみられなかった。 …
- NAID 110001723281
- Decrease in Surface Charge Density of Klebsiella pneumoniae Treated with Cefodizime and Enhancement of the Phagocytic Function of Human Polymorphonuclear Leucocytes Stimulated by the Drug-Treated Bacteria
- 邨次 誠,三宅 美行,石田 直文,兵頭 昭夫,寺山 和幸
- Biological & pharmaceutical bulletin 18(9), 1259-1263, 1995-09-15
- … Treatment of Klebsiella pneumoniae 109 with cefodizime, ceftazidime, cefbuperazone, cefotaxime or flomoxef at a sub-minimum inhibitory concentration (sub-MIC) (1/4 MIC) for 1 h altered its morphology. … pneumoniae, more easily than ceftazidime, cefbuperazone, cefotaxime or flomoxef, followed by an increase in the phagocytic activity of PMNs. …
- NAID 110003641034
Related Links
- Cefbuperazone [CBPZ] セフブペラゾン, セフェム系(Cephamycin型 ureid型 MTT基) 1. 商品名 先発品 トミポラン静注用1g 【富山化学工業, 大正富山医薬品】 2. 日本における発売年 1985(昭和60)年 3. 特長 グラム陽性、陰性菌から ...
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- 関
- ハフニア属、腸内細菌科
参考
- http://www.antibiotic-books.jp/germs/30?q=Hafnia+alvei
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- セフブペラゾンナトリウム cefbuperazone sodium
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