セフォペラゾン
WordNet
- a parenteral cephalosporin (trade name Cefobid) used for severe infections (同)Cefobid
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/06/21 01:20:17」(JST)
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Cefoperazone
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Systematic (IUPAC) name |
(6R,7R)-7-[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
MedlinePlus |
a601206 |
Pregnancy cat. |
? |
Legal status |
? |
Pharmacokinetic data |
Excretion |
Hepatic |
Identifiers |
CAS number |
62893-19-0 |
ATC code |
J01DD12 QJ51DD12 |
PubChem |
CID 44185 |
DrugBank |
DB01329 |
ChemSpider |
40206 Y |
UNII |
7U75I1278D Y |
KEGG |
D07645 Y |
ChEMBL |
CHEMBL507674 Y |
Chemical data |
Formula |
C25H27N9O8S2 |
Mol. mass |
645.67 g/mol |
SMILES
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)NC(=O)N4C(=O)C(=O)N(CC)CC4)CSc5nnnn5C)C(=O)O
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InChI
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InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1 Y
Key:GCFBRXLSHGKWDP-XCGNWRKASA-N Y
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Y (what is this?) (verify)
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Cefoperazone is a third generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid, and also marked by pharco B international under the name of Cefazone and also marketed by "sigmatec" under the name "cefoperazone". It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.
Cefina-SB is a combination of sulbactam and cefoperazone. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis, and sulbactam acts as a beta-lactamase inhibitor, to increase the antibacterial activity of cefoperazone against beta-lactamase producing organisms. In some countries, the combination is sold as Sulperazone. Gepach International markets this combination of Cefoperazone with Sulbactam under the brand name Bacperazone
Adverse effects[edit]
Cefoperazone contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[1]
References[edit]
- ^ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
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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UpToDate Contents
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- 1. セフェム系 cephalosporins
- 2. 緑膿菌感染症に対する抗菌薬治療の原則 principles of antimicrobial therapy of pseudomonas aeruginosa infections
- 3. 鼻疽の治療および予後 treatment and prognosis of melioidosis
- 4. 眼、耳、尿路、胃腸管、および中枢神経系における緑膿菌感染症 pseudomonas aeruginosa infections of the eye ear urinary tract gastrointestinal tract and central nervous system
- 5. 水曝露後の軟部組織感染 soft tissue infections following water exposure
English Journal
- Influence of hybrid inorganic/organic mesoporous and nanostructured materials on the cephalosporins' efficacy on different bacterial strains.
- Carmen Chifiriuc M, Mihaiescu D, Ilinca E, Marutescu L, Mihaescu G, Mihai Grumezescu A.SourceUniversity of Bucharest, Faculty of Biology, Department of Microbiology and Immunology, Bucharest, Romania.
- IET nanobiotechnology / IET.IET Nanobiotechnol.2012 Dec;6(4):156-61. doi: 10.1049/iet-nbt.2011.0066.
- The aim of this study was to investigate the effect of different hybrid inorganic-organic micro- and nanomaterials (Fe(3)O(4)/PEG(600), Fe(3)O(4)/C(12), ZSM-5) on the antibacterial activity of different cephalosporins against Gram-positive and Gram-negative bacterial strains. The synergic effect of
- PMID 23101869
- A pilot study on water pollution and characterization of multidrug-resistant superbugs from Byramangala tank, Ramanagara district, Karnataka, India.
- Skariyachan S, Lokesh P, Rao R, Kumar AU, Vasist KS, Narayanappa R.SourceR & D Centre, Department of Biotechnology, Dayananda Sagar College of Engineering, Bangalore, 560-078, Karnataka, India, sinoshskariya@gmail.com.
- Environmental monitoring and assessment.Environ Monit Assess.2012 Nov 1. [Epub ahead of print]
- Urbanization and industrialization has increased the strength and qualities of municipal sewage in Bangalore, India. The disposal of sewage into natural water bodies became a serious issue. Byramangala reservoir is one such habitat enormously polluted in South India. The water samples were collected
- PMID 23114918
Japanese Journal
- Nosocomial pneumonia: Search for an empiric and effective antibiotic regimen in high burden tertiary care centre
- Gupta Nitin,Soneja Manish,Ray Yogiraj,Sahu Monalisa,Vinod Kutty Sharada,Kapil Arti,Biswas Ashutosh,Wig Naveet,Sood Rita
- Drug Discoveries & Therapeutics 12(2), 97-100, 2018
- … Cefoperazone-sulbactam (43%) had the best sensitivity pattern overall. … Cefoperazone-sulbactam plus amikacin (56%) was the combination with the best combined sensitivity overall. …
- NAID 130006734045
- Molecular characteristics and virulence analysis of eight <i>Aeromonas hydrophila</i> isolates obtained from diseased Amur sturgeon <i>Acipenser schrenckii</i> Brandt, 1869
- ZHOU Yong,FAN Yuding,JIANG Nan,LIU Wenzhi,SHI Yuheng,ZHAO Jianqing,ZENG Lingbing
- The Journal of Veterinary Medical Science 80(3), 421-426, 2018
- … The antibiotics ceftazidime, cefuroxime, cefoperazone, cefotaxime, ceftriaxone, aztreonam, and cefepime appeared effective against them. …
- NAID 130006539120
- High Rates of Contamination of Poultry Meat Products with Drug-Resistant <i>Campylobacter</i> in Metro Manila, Philippines
- Lim Patrick Wilson N.,Tiam-Lee Daphne C.,Paclibare Phyllis Anne P.,Subejano Ma. Socorro Edden P.,Cabero-Palma Juvy Ann S.,Penuliar Gil M.
- Japanese Journal of Infectious Diseases 70(3), 311-313, 2017
- … was isolated on modified charcoal cefoperazone deoxycholate agar plates and identified through biochemical tests and PCR amplification of genus- and species-specific genes. …
- NAID 130005671812
Related Links
- Cefoperazone [CPZ] セフォペラゾン, セフェム系(ureid型 MTT基) 1. 商品名 先発品 セフォビッド注射用1g 【ファイザー】 セフォペラジン筋注用1g 【富山化学工業, 大正富山医薬品】 セフォペラジン注射用0.5g/セフォペラジン注射用 1g ...
- Sulbactam / Cefoperazone [SBT/CPZ] スルバクタム/セフォペラゾン, セフェム系(ureid型 MTT基 β-ラクタマーゼ阻害剤配合) 1. 商品名 先発品 スルペラゾン静注用0.5g/スルペラゾン静注用1g/スルペラゾンキット静注用1g 【ファイザー】 ...
Related Pictures
★リンクテーブル★
[★]
- 英
- ceftazidime, CAZ
- 商
- Fortaz, Ceptaz, Tazicer, Taxidime。セパダシン、モダケミン、モダシン、モベンゾシン
- 関
- セファロスポリン系抗菌薬
-
-
抗菌スペクトル
効果・効能
- モダシン静注用
適応菌種
- 本剤に感性のブドウ球菌属、レンサ球菌属、肺炎球菌、大腸菌、シトロバクター属、クレブシエラ属、エンテロバクター属、セラチア属、プロテウス属、モルガネラ・モルガニー、プロビデンシア属、インフルエンザ菌、シュードモナス属、緑膿菌、バークホルデリア・セパシア、ステノトロホモナス(ザントモナス)・マルトフィリア、アシネトバクター属、ペプトストレプトコッカス属、バクテロイデス属、プレボテラ属(プレボテラ・ビビアを除く)
適応症
- 敗血症、感染性心内膜炎、外傷・熱傷及び手術創等の二次感染、咽頭・喉頭炎、扁桃炎(扁桃周囲炎、扁桃周囲膿瘍を含む)、急性気管支炎、肺炎、肺膿瘍、膿胸、慢性呼吸器病変の二次感染、膀胱炎、腎盂腎炎、前立腺炎(急性症、慢性症)、腹膜炎、胆嚢炎、胆管炎、肝膿瘍、バルトリン腺炎、子宮内感染、子宮付属器炎、子宮旁結合織炎、化膿性髄膜炎、中耳炎、副鼻腔炎
[★]
- 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
- cefoperazone CPZ
- ラ
- cefoperazonum
- 化
- cefoperazone sodium セフォペラゾンナトリウム
- 商
- CEFOBID。スペルゾン、スルタムジン、スルペゾール、スルペラゾン、セフォセフ、セフォビッド、セフォペラジン、セフォン、セフロニック、ナスパルン、バクフォーゼ、ワイスタール
- 関
- セファロスポリン系抗菌薬
-
-
抗菌スペクトル
[★]
- 関
- ハフニア属、腸内細菌科
参考
- http://www.antibiotic-books.jp/germs/30?q=Hafnia+alvei
[★]
- 関
- cefoperazone
- 同
- Cefobid