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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/07/08 11:51:59」(JST)
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Cefoxitin
|
Systematic (IUPAC) name |
(6 S,7 R)-3-(carbamoyloxymethyl)-7-methoxy-
8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-
1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
|
Clinical data |
Trade names |
Mefoxin |
AHFS/Drugs.com |
Monograph |
MedlinePlus |
a682737 |
Pregnancy
category |
|
Routes of
administration |
IV |
Pharmacokinetic data |
Metabolism |
minimal |
Biological half-life |
41-59 min |
Excretion |
85% urine |
Identifiers |
CAS Number |
35607-66-0 Y |
ATC code |
J01DC01 (WHO) |
PubChem |
CID 441199 |
DrugBank |
DB01331 N |
ChemSpider |
389981 Y |
UNII |
6OEV9DX57Y Y |
KEGG |
D02345 N |
ChEBI |
CHEBI:209807 N |
ChEMBL |
CHEMBL996 N |
Chemical data |
Formula |
C16H17N3O7S2 |
Molar mass |
427.454 g/mol |
SMILES
-
O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)Cc3sccc3)COC(=O)N)C(=O)O
|
InChI
-
InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1 Y
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Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N Y
|
NY (what is this?) (verify) |
Cefoxitin is a cephamycin antibiotic developed by Merck & Co., Inc., often grouped with the second−generation cephalosporins. It is sold under the brand name Mefoxin.
Microbiology
Cefoxitin acts by interfering with cell wall synthesis. Its activity spectrum includes a broad range of gram-negative and gram-positive bacteria including anaerobes. It is inactive in vitro to most strains of Pseudomonas aeruginosa and many strains of Enterobacter cloacae. Staphylococci resistant to methicillin/oxacillin should be considered resistant to cefoxitin.[1]
Cefoxitin is considered to be a strong beta-lactamase inducer, as are certain other antibiotics (such as imipenem).[2]
Spectrum of Bacterial Susceptibility
Cefoxitin has a broad spectrum of activity and has been used in the treatment of skin, bone, respiratory and urinary tract infections. Susceptible bacteria include some Staphylococci, Enterococci, Streptococci, and others. The following represents MIC susceptibility data for a few medically significant microorganisms.
- Escherichia coli: 0.2 μg/ml – 64 μg/ml
- Haemophilus influenzae: 0.5 μg/ml – 12.5 μg/ml
- Streptococcus pneumoniae: 0.2 μg/ml – 1 μg/ml
[3]
References
- ^ Mefoxin Official FDA information at Drugs.com
- ^ Phillips I, Shannon K (1993). "Importance of beta-lactamase induction". Eur J Clin Microbiol Infect Dis. 12 Suppl 1: S19–26. PMID 8477758.
- ^ http://www.toku-e.com/Assets/MIC/Cefoxitin.pdf
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
|
|
β-lactams/
(Inhibit PBP
cross-links) |
|
|
Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
UpToDate Contents
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English Journal
- Staphylococci isolated from ready-to-eat meat - Identification, antibiotic resistance and toxin gene profile.
- Fijałkowski K1, Peitler D2, Karakulska J2.
- International journal of food microbiology.Int J Food Microbiol.2016 Dec 5;238:113-120. doi: 10.1016/j.ijfoodmicro.2016.09.001. Epub 2016 Sep 5.
- The aim of this study was to analyse the staphylococci isolated from ready-to-eat meat products, including pork ham, chicken cold cuts, pork sausage, salami and pork luncheon meat, sliced in the store to the consumer's specifications, along with species identification and determination of antibiotic
- PMID 27614422
- Methicillin-resistant Staphylococcus aureus isolates with SCCmec type V and spa types t437 or t1081 associated to discordant susceptibility results between oxacillin and cefoxitin, Central Taiwan.
- Ho CM1, Lin CY2, Ho MW3, Lin HC4, Chen CJ5, Lin LC6, Lu JJ7.
- Diagnostic microbiology and infectious disease.Diagn Microbiol Infect Dis.2016 Dec;86(4):405-411. doi: 10.1016/j.diagmicrobio.2016.08.025. Epub 2016 Aug 28.
- Staphylococcus aureus isolates with discordant susceptibility results between oxacillin and cefoxitin obtained using automated microbiology systems are infrequently observed. From April 2013 to December 2014, 1956 methicillin-resistant S. aureus (MRSA) and 1761 methicillin-susceptible S. aureus isol
- PMID 27650515
- Disk Diffusion Testing for Detection of Methicillin-Resistant Staphylococci: Does Moxalactam Improve upon Cefoxitin?
- Bonjean M1, Hodille E1,2,3, Dumitrescu O1,2,3, Dupieux C1,2,3, Nkoud Mongo C1, Allam C1, Beghin M1, Paris M1, Borrel O1, Chardon H4, Laurent F1,2,3, Rasigade JP1,2,3, Lina G5,2,3.
- Journal of clinical microbiology.J Clin Microbiol.2016 Dec;54(12):2905-2909. Epub 2016 Sep 14.
- Disk diffusion testing is widely used to detect methicillin resistance in staphylococci, and cefoxitin is currently considered the best marker for mecA-mediated methicillin resistance. In low-inoculum diffusion testing (colony suspension at 106 CFU/ml), the addition of moxalactam in combination with
- PMID 27629897
Japanese Journal
- Characterization of methicillin-resistant Staphylococcus spp. isolated from dogs in Korea
- Jang Yunho,Bae Dong hwa,Cho Jae-Keun,Bahk Gyung Jin,Lim Suk-Kyung,Lee Young Ju
- Japanese Journal of Veterinary Research 62(4), 163-170, 2014-11
- … Among the 36 MRS isolates tested, 100% were resistant to oxacillin and penicillin, and at least 50% were resistant to sulfamethoxazole/trimethoprim (69.4%), erythromycin (63.9%), tetracycline (58.3%), cefoxitin (55.6%), clindamycin (50.0%) or pirlimycin (50.0%). …
- NAID 120005517704
- In Vitro Antibiotic Susceptibility of Francisella tularensis Isolates from Japan
- , , [他], , , , ,
- Japanese Journal of Infectious Diseases 66(6), 534-536, 2013
- … The susceptibility to seven other β-lactams (aztreonam, cefotaxime, cefoxitin, ceftriaxone, cefuroxime, imipenem, and meropenem) varied among the isolates. …
- NAID 130003390336
- Clostridium difficile Isolated from the Fecal Contents of Swine in Japan
- , , , , ,
- Journal of Veterinary Medical Science 75(4), 539-541, 2013
- … A total of 250 fecal content samples were collected from 25 farrow-to-finish pig farms and examined for the prevalence of Clostridium difficile by using ethanol treatment followed by plating onto selective media-cycloserine-cefoxitin-mannitol agar-for the isolation of Clostridium difficile. …
- NAID 130002502188
Related Links
- セフォキシチン(Cefoxitin; Mefoxin®, Mefoxitin®); セフォテタン(Cefotetan; Apacef®, Cefotan®, Yamatetan®); セフメタゾール(Cefmetazole; Cefmeazon®, ... セフォキシチン, cefoxitin, CFX, セフォキシチンナトリウム, マーキシン, 第二世代 セフェム ...
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