cefoxitin [Antibiotic]

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Accession ARO:0000008
Synonym(s)FOX mefoxin Mefoxitin
DefinitionCefoxitin is a cephamycin antibiotic often grouped with the second generation cephalosporins. Cefoxitin is bactericidal and acts by inhibiting the synthesis of the peptidoglycan layer of bacterial cell walls. The peptidoglycan layer is important for cell wall structural integrity, especially in Gram-positive organisms. Cefoxitin's 7-alpha-methoxy group and 3' leaving group make it a poor substrate for most beta-lactamases.
SMILESCO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21
PubChem441199
ChEBI209807
CAS35607-66-0
ChEMBLCHEMBL996
Drug Classcephalosporin
Classification4 ontology terms | Show
Parent Term(s)1 ontology terms | Show
Sub-Term(s)
26 ontology terms | Show
+ beta-lactam sensitive penicillin-binding protein targeted_by_antibiotic
+ CfxA confers_resistance_to_antibiotic
+ CAM-1 confers_resistance_to_antibiotic
+ Serratia marcescens Omp1 confers_resistance_to_antibiotic
+ Klebsiella pneumoniae OmpK37 confers_resistance_to_antibiotic
+ Burkholderia pseudomallei Omp38 confers_resistance_to_antibiotic
+ CMY-42 confers_resistance_to_antibiotic
+ NDM-5 confers_resistance_to_antibiotic
+ NmcA confers_resistance_to_antibiotic
+ CMY-2 confers_resistance_to_antibiotic
+ blaS1 confers_resistance_to_antibiotic
+ CTX-M-3 confers_resistance_to_antibiotic
+ PDC-3 confers_resistance_to_antibiotic
+ PDC-5 confers_resistance_to_antibiotic
+ Klebsiella pneumoniae OmpK35 confers_resistance_to_antibiotic
+ blaC confers_resistance_to_antibiotic
+ YRC-1 confers_resistance_to_antibiotic
+ PJM-1 confers_resistance_to_antibiotic
+ SSA confers_resistance_to_antibiotic
+ LAQ-1 confers_resistance_to_antibiotic
+ PSZ-1 confers_resistance_to_antibiotic
+ CDA-1 confers_resistance_to_antibiotic
+ AMZ-1 confers_resistance_to_antibiotic
+ cefoxitin-clavulanate [Antibiotic+Adjuvant] has_part
+ cefoxitin-sulbactam [Antibiotic+Adjuvant] has_part
+ cefoxitin-tazobactam [Antibiotic+Adjuvant] has_part
Publications

Jacoby GA and Munoz-Price LS. 2005. N Engl J Med 352(4): 380-391. The new beta-lactamases. (PMID 15673804)

Bradford PA. 2001. Clin Microbiol Rev 14(4): 933-951. Extended-spectrum beta-lactamases in the 21st century: characterization, epidemiology, and detection of this important resistance threat. (PMID 11585791)

Faraci WS and Pratt RF. 1986. Biochemistry 25(10): 2934-2941. Mechanism of inhibition of RTEM-2 beta-lactamase by cephamycins: relative importance of the 7 alpha-methoxy group and the 3' leaving group. (PMID 3487346)

Curator Acknowledgements
Curator Description Most Recent Edit