セフォテタン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/03/15 11:35:11」(JST)
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Cefotetan
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Systematic (IUPAC) name |
(7S)-7-{[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)
1,3-dithietane-2-carbonyl]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 |
Consumer Drug Information |
Legal status |
? |
Identifiers |
CAS number |
69712-56-7 Y |
ATC code |
J01DC05 |
PubChem |
CID 53025 |
DrugBank |
DB01330 |
ChemSpider |
47904 Y |
UNII |
48SPP0PA9Q Y |
KEGG |
D00260 N |
ChEBI |
CHEBI:3499 N |
ChEMBL |
CHEMBL474579 N |
Chemical data |
Formula |
C17H17N7O8S4 |
Mol. mass |
575.623 g/mol |
SMILES
- O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)C3S/C(S3)=C(/C(=O)N)C(=O)O)CSc4nnnn4C)C(=O)O
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InChI
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InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15-,17+/m1/s1 Y
Key:SRZNHPXWXCNNDU-IXOPCIAXSA-N Y
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N (what is this?) (verify) |
Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.
Cefotetan was developed by Yamanouchi. It is marketed outside Japan by AstraZeneca with the brand names Apatef and Cefotan.
Contents
- 1 Adverse effects
- 2 Spectrum of bacterial susceptibility
- 3 References
- 4 External links
Adverse effects[edit]
The chemical structure of cefotetan, 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[edit]
Cefotetan has a broad spectrum of activity and has been used to treat bacterial infections of the bone, skin, urinary tract, and lower respiratory tract. Notable species include Bacteroides, Streptococcus, and Escherichia. The following represents MIC susceptibility data for a few medically significant bacteria.
- Escherichia coli: 0.06 µg/mL
- Bacteroides fragilis: ≤0.06 µg/mL - 512 µg/mL
- Clostridium perfringins: 1 µg/mL - 4 µg/mL
[2]
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.
- ^ http://www.toku-e.com/Assets/MIC/Cefotetan.pdf
External links[edit]
- Cefotan official web site run by AstraZeneca US
- Cefotetan entry in 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) |
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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|
|
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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
- The identification, typing, and antimicrobial susceptibility of Pseudomonas aeruginosa isolated from mink with hemorrhagic pneumonia.
- Qi J1, Li L2, Du Y1, Wang S3, Wang J1, Luo Y2, Che J4, Lu J4, Liu H5, Hu G5, Li J6, Gong Y6, Wang G7, Hu M8, Shiganyan8, Liu Y9.
- Veterinary microbiology.Vet Microbiol.2014 Jun 4;170(3-4):456-61. doi: 10.1016/j.vetmic.2014.02.025. Epub 2014 Feb 25.
- The biological characteristics and molecular epidemiology of Pseudomonas aeruginosa associated with mink hemorrhagic pneumonia from Shandong province of eastern China were determined in this study. From 2010 to 2011, 30 mink P. aeruginosa isolates were identified from lung, fecal and feed samples of
- PMID 24629901
- The changes of PCR ribotype and antimicrobial resistance of Clostridium difficile in a tertiary care hospital in Korea over 10 years.
- Lee JH1, Lee Y, Lee K, Riley TV, Kim H.
- Journal of medical microbiology.J Med Microbiol.2014 Apr 2. doi: 10.1099/jmm.0.072082-0. [Epub ahead of print]
- The aims of this study were to investigate any change in PCR ribotypes and to determine the antimicrobial resistance of common PCR ribotypes over a 10-year period in a tertiary care hospital. We conducted PCR ribotyping, antimicrobial susceptibility testing, and DNA gyrase sequencing to identify cha
- PMID 24696516
- Microbiological Spectrum and Antibiotic Sensitivity in Endophthalmitis: A 25-Year Review.
- Gentile RC1, Shukla S2, Shah M3, Ritterband DC2, Engelbert M4, Davis A5, Hu DN3.
- Ophthalmology.Ophthalmology.2014 Apr 2. pii: S0161-6420(14)00105-5. doi: 10.1016/j.ophtha.2014.02.001. [Epub ahead of print]
- PURPOSE: To identify the spectrum and susceptibility pattern of pathogens responsible for culture-positive endophthalmitis referred to a single institution and investigate possible trends in both pathogens and antibiotic sensitivities over the past 25 years.DESIGN: A retrospective, laboratory-based
- PMID 24702755
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