- 関
- cefmetazole
WordNet
- a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11
PrepTutorEJDIC
- ソジウム,ナトリウム(金属元素;化学記号はNa)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/08/29 14:23:27」(JST)
[Wiki en表示]
Cefmetazole
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| Systematic (IUPAC) name |
| (6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| MedlinePlus |
a601206 |
| Legal status |
? |
| Identifiers |
| CAS number |
56796-20-4 Y |
| ATC code |
J01DC09 |
| PubChem |
CID 42008 |
| DrugBank |
DB00274 |
| ChemSpider |
38311 Y |
| UNII |
3J962UJT8H Y |
| KEGG |
D00910 Y |
| ChEBI |
CHEBI:3489 Y |
| ChEMBL |
CHEMBL1201195 N |
| Chemical data |
| Formula |
C15H17N7O5S3 |
| Mol. mass |
471.538 g/mol |
SMILES
- O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O
|
InChI
-
InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1 Y
Key:SNBUBQHDYVFSQF-HIFRSBDPSA-N Y
|
| N (what is this?) (verify) |
Cefmetazole is a cephalosporin antibiotic, usually grouped with the second-generation cephalosporins.
Adverse effects
The chemical structure of cefmetazole, like that of several other cephalosporins, 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]
Spectrum of bacterial susceptibility
Cefmetazole is a broad-spectrum cephalosporin antimicrobial and has been effective in treating bacteria responsible for causing urinary tract and skin infections. The following represents MIC susceptibility data for a few medically significant microorganisms.
- Bacteroides fragilis: 0.06 - >256 µg/ml
- Clostridium difficile: 8 - >128 µg/ml
- Staphylococcus aureus: 0.5 - 256 µg/ml (includes MRSA)
[2]
References
- ^ 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.
- ^ http://www.toku-e.com/Assets/MIC/Cefmetazole%20free%20acid.pdf
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Antibacterials: cell envelope antibiotics (J01C-J01D)
|
|
| Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
|
|
| Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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|
β-lactams/
(inhibit PBP
cross-links) |
|
Penicillins
(penams)
|
|
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
|
|
|
Narrow sp.
|
|
β-lactamase sensitive
|
- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
|
|
|
β-lactamase resistant
|
- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
|
|
|
|
|
Penems
|
|
|
|
Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
|
|
|
Cephalosporins/Cephamycins
(cephems)
|
|
1st (PEcK)
|
- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
|
|
|
2nd (HEN)
|
- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
|
|
|
3rd
|
- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
|
|
|
4th (antipseudomonal)
|
- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
|
|
|
5th
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- Ceftobiprole
- Ceftaroline fosamil
|
|
|
Veterinary
|
- Ceftiofur
- Cefquinome
- Cefovecin
|
|
|
|
Monobactams
|
- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
|
|
|
β-lactamase inh.
|
- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
|
|
|
Combinations
|
- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
|
|
|
| Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (lysozyme)
- Gramicidin
- Isoniazid
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
|
gr+f/gr+a (t)/gr-p (c)/gr-o
|
drug (J1p, w, n, m, vacc)
|
|
|
|
UpToDate Contents
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English Journal
- The Dynamic Observation of Plasma Concentration of Antimicrobial Agents During Balanced Ultrafiltration In Vitro.
- Fang Y, Guan Y, Wan C, Fu Z, Jiang J, Wu C, Zhao J, Sun P, Long C.SourceDepartment of Extracorporeal Circulation, State Key Laboratory of Cardiovascular Disease, Fuwai Hospital, National Center for Cardiovascular Diseases, Chinese Academy of Medical Sciences and Peking Union Medical College, China.
- Artificial organs.Artif Organs.2013 Jul 19. doi: 10.1111/aor.12113. [Epub ahead of print]
- Routine perioperative intravenous antimicrobial agents are administered as surgical prophylaxis. However, whether balanced ultrafiltration during extracorporeal circulation has substantial effect on the concentration of antimicrobial agents remains unclear. The concentrations of antimicrobial agents
- PMID 23865445
- Citrobacter peritoneal dialysis peritonitis: rare occurrence with poor outcomes.
- Chao CT, Lee SY, Yang WS, Chen HW, Fang CC, Yen CJ, Chiang CK, Hung KY, Huang JW.Source1. Department of Traumatology, National Taiwan University Hospital, Taipei, Taiwan; ; 2. Division of Nephrology, Department of Internal Medicine; National Taiwan University Hospital, Taipei, Taiwan;
- International journal of medical sciences.Int J Med Sci.2013 Jul 4;10(9):1092-8. doi: 10.7150/ijms.6251. Print 2013.
- Introduction: Non-Pseudomonas gram-negative bacteria are responsible for an increasing proportion of cases of peritoneal dialysis (PD)-related peritonitis. The role of Citrobacter species in the etiology of PD-related peritonitis is often underestimated. In the present study, we aimed to describe th
- PMID 23869184
- Non-cytotoxic nanomaterials enhance antimicrobial activities of cefmetazole against multidrug-resistant Neisseria gonorrhoeae.
- Li LH, Yen MY, Ho CC, Wu P, Wang CC, Maurya PK, Chen PS, Chen W, Hsieh WY, Chen HW.SourceGraduate Institute of Toxicology, College of Medicine, National Taiwan University, Taipei, Taiwan.
- PloS one.PLoS One.2013 May 21;8(5):e64794. doi: 10.1371/journal.pone.0064794. Print 2013.
- The emergence and spread of antibiotic-resistant Neisseria gonorrhoeae has led to difficulties in treating patients, and novel strategies to prevent and treat this infection are urgently needed. Here, we examined 21 different nanomaterials for their potential activity against N. gonorrhoeae (ATCC 49
- PMID 23705013
Japanese Journal
- 再発を繰り返した Clostridium difficile 関連下痢症の1例 : 分離菌株のPCRリボタイピングによる検討
- 加藤 秀章,西 祐二,大山 展,中村 誠,泉田 さゆり,橋本 政治,加藤 はる
- 日本消化器病學會雜誌 = The Japanese journal of gastro-enterology 103(2), 168-173, 2006-02-05
- Clostridium difficile関連下痢症(CDAD)は，その約20%に再発が認められる.2度の再発を来したCDAD患者より分離された菌株をPCRリボタイピング法を用いて検討した.初発時および再発時の糞便からはタイプsmz菌株が検出され，持続感染株による再燃が，再々発時の糞便からはタイプhr菌株が検出され，新たな菌株による感染が，各々の再発の機序として考えられた.CDADの再発は解決すべ …
- NAID 10017559955
- Preventive Effect of Eye Drops of Liposomes Containing Disulfiram and Cefmetazole on Selenite-Induced Cataract in Rat Pups
- Ito Yoshimasa,Nagai Noriaki,Cai Hong [他],TAKEDA Maki,KOIZUMI Yuichi
- Journal of Oleo Science 55(1), 15-22, 2006
- … Disulfiram (DSF) and cefmetazole (CMZ), which possess with anti-oxidative activities were tested for anti-cataract effect in rats and were compared with pirenoxine (PRX), which is a marketed product used for the treatment of cataract. … The reduced form of glutathione (GSH) content of the lenses was decreased by approximately 60% of normal level 96 h after the sodium selenite-injection and the calcium (Ca2+) content was increased. …
- NAID 130000055608
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- cefmetazole CMZ
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- cefmetazolum
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- セフメタゾールナトリウム cefmetazole sodium
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