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Cefoxitin information


Cefoxitin
Clinical data
Trade namesMefoxin, Renoxitin, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682737
License data
  • US DailyMed: Cefoxitin
Pregnancy
category
  • AU: B1
Routes of
administration
Intravenous
ATC code
  • J01DC01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNING[2]Rx-only[3]
Pharmacokinetic data
Metabolismminimal
Elimination half-life41-59 min
Excretion85% urine
Identifiers
IUPAC name
  • (6R,7S)-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
CAS Number
  • 35607-66-0 checkY
PubChem CID
  • 441199
DrugBank
  • DB01331 ☒N
ChemSpider
  • 389981 checkY
UNII
  • 6OEV9DX57Y
KEGG
  • D02345 ☒N
  • as salt: D00913 ☒N
ChEBI
  • CHEBI:209807 ☒N
ChEMBL
  • ChEMBL996 ☒N
CompTox Dashboard (EPA)
  • DTXSID1022764 Edit this at Wikidata
ECHA InfoCard100.047.841 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O7S2
Molar mass427.45 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point149 to 150 °C (300 to 302 °F) (dec.)
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 checkY
  • Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It was synthesized in order to create an antibiotic with a broader spectrum.[4] It is often grouped with the second-generation cephalosporins.[5] Cefoxitin requires a prescription and as of 2010 is sold under the brand name Mefoxin by Bioniche Pharma, LLC. The generic version of cefoxitin is known as cefoxitin sodium.[6][7]

  1. ^ "Cefoxitin International". Drugs.com. 2 November 2020. Retrieved 8 November 2020.
  2. ^ "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.
  3. ^ Cite error: The named reference Cefoxitin FDA label was invoked but never defined (see the help page).
  4. ^ Gootz TD (January 1990). "Discovery and development of new antimicrobial agents". Clinical Microbiology Reviews. 3 (1): 13–31. doi:10.1128/cmr.3.1.13. PMC 358138. PMID 2404566.
  5. ^ Levy SB (2013-11-11). The Antibiotic Paradox: How Miracle Drugs Are Destroying the Miracle. Springer. ISBN 978-1-4899-6042-9.
  6. ^ "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Retrieved 2017-05-04.
  7. ^ "Supplement Approval" (PDF). Food and Drug Administration. Department of Health and Human Services.

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Cefoxitin

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Cefoxitin is a second-generation cephamycin antibiotic developed by Merck & Co., Inc. from Cephamycin C in the year following its discovery, 1972. It...

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Peritonitis

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and Gram-negative organisms must be covered. Out of the cephalosporins, cefoxitin and cefotetan can be used to cover Gram-positive bacteria, Gram-negative...

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Cephamycin

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is lacking for this indication.[citation needed] Cephamycins include: Cefoxitin Cefotetan Cefmetazole Oreste A. Mascaretti (2003). Bacteria Versus Antibacterial...

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Timeline of antibiotics

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amikacin 1977 – azlocillin 1977 – cefadroxil 1977 – cefamandole 1977 – cefoxitin 1977 – cefuroxime 1977 – mezlocillin 1977 – pivmecillinam 1979 – cefaclor...

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Cephalosporin

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cefapirin, cefradine, and cefadroxil are drugs belonging to this group. Cefoxitin, cefuroxime, cefaclor, cefprozil, and cefmetazole are classed as second-generation...

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Pelvic inflammatory disease

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administered to them as inpatients or outpatients. Typical regimens include cefoxitin or cefotetan plus doxycycline, and clindamycin plus gentamicin. An alternative...

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Capnocytophaga

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third-generation cephalosporins, but remain susceptible to imipenem, cefoxitin, and amoxicillin combined with clavulanic acid. Although resistant strains...

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Bacteroides fragilis

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have displayed increasing resistance to antimicrobial agents such as cefoxitin, clindamycin, metronidazole, carbapenems, & fluoroquinolones. Resistance...

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List of antibiotics

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disrupt the synthesis of the peptidoglycan layer of bacterial cell walls. Cefoxitin Cefotetan Cefotan Cefamandole Cefmetazole Cefonicid Loracarbef Cefprozil...

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Doxycycline

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pelvic inflammatory disease: comparison of cefotetan plus doxycycline and cefoxitin plus doxycycline". American Journal of Obstetrics and Gynecology. 158...

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Bilophila wadsworthia

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This bacterium is susceptible to the β-lactam antibiotics imipenem, cefoxitin, and ticarcillin. B. wadsworthia is a Gram-negative, catalase-positive...

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Benzathine benzylpenicillin

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Cefuroxime axetil Cefamandole‡ Cefonicid‡ Ceforanide‡ Cefuzonam‡ Cephamycin (Cefoxitin Cefotetan Cefminox‡ Cefbuperazone‡ Cefmetazole‡) Carbacephem (Loracarbef‡)...

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Proteus penneri

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resistance of P. penneri to cefuroxime and the marked inhibitory activity of cefoxitin against this species also distinguishes P. penneri from the other Proteus...

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List of infectious diseases

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on symptoms, ultrasound, laparoscopic surgery Typical regimens include cefoxitin or cefotetan plus doxycycline, and clindamycin plus gentamicin. No Bordetella...

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Mycobacterium

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fevers, chills, muscle aches. clarithromycin, azithromycin, amikacin, cefoxitin, imipenem. 3000 (US, Annual estimated) M. abscessus complex Coughing,...

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Side effects of penicillin

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Cefuroxime axetil Cefamandole‡ Cefonicid‡ Ceforanide‡ Cefuzonam‡ Cephamycin (Cefoxitin Cefotetan Cefminox‡ Cefbuperazone‡ Cefmetazole‡) Carbacephem (Loracarbef‡)...

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Veillonella parvula

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Tsai JC, Liaw SJ, Ho SW, Luh KT (September 2002). "High incidence of cefoxitin and clindamycin resistance among anaerobes in Taiwan". Antimicrobial Agents...

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MecA

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gel electrophoresis, which can be costly, tedious, and unpredictable. cefoxitin disc diffusion uses phenotypic resistance to test not only for methicillin...

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Staphylococcus pseudintermedius

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using biochemical or phenotypic methods, such as disc diffusion. Although cefoxitin disks have been used, oxacillin disks are considered to be much more sensitive...

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Pluralibacter gergoviae

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rifampicin, fusidic acid, and fosfomycin. P. gergoviae is also resistant to cefoxitin, likely due to β-lactamase production. Brenner, D. J.; Richard, C.; Steigerwalt...

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Anaerobic infection

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for most infections are metronidazole, clindamycin, chloramphenicol, cefoxitin, a penicillin (i.e. ticarcillin, ampicillin, piperacillin) and a beta-lactamase...

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Acute generalized exanthematous pustulosis

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Penicillin, ampicillin, amoxicillin, clindamycin, cephalexin, cefepime, cefoxitin, cefazolin, various sulfonamides, various quinolones, vancomycin, levofloxacin...

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ATC code J01

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Cefradine J01DB10 Cefacetrile J01DB11 Cefroxadine J01DB12 Ceftezole J01DC01 Cefoxitin J01DC02 Cefuroxime J01DC03 Cefamandole J01DC04 Cefaclor J01DC05 Cefotetan...

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