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Cefoxitin

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This is an old revision of this page, as edited by Beetstra (talk | contribs) at 13:11, 12 December 2010 (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 13:11, 12 December 2010 by Beetstra (talk | contribs) (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Cefoxitin
Clinical data
Pregnancy
category
  • B
Routes of
administration		IV
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolismminimal
Elimination half-life41-59 min
Excretion85% urine
Identifiers
IUPAC name
  • (6S,7R)-4-(carbamoyloxymethyl)-7-methoxy-
    8-oxo-7--5-thia-
    1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.047.841 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O7S2
Molar mass427.454 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS12(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
  • Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
  (verify)

Cefoxitin is a cephamycin antibiotic developed by Merck & Co., Inc., often grouped with the second−generation cephalosporins. It is also known as 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 enterococci and many strains of Enterobacter cloacae. Staphylococci resistant to methicillin/oxacillin should be considered resistant to cefoxitin.

Cefoxitin is considered a strong beta-lactamase inducer, as are certain other antibiotics (such as imipenem).

References

  1. "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. Mefoxin Official FDA information at Drugs.com
  3. Phillips I, Shannon K (1993). "Importance of beta-lactamase induction". Eur J Clin Microbiol Infect Dis. 12 Suppl 1: S19–26. PMID 8477758.
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
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