Cefoxitin

Cefoxitin
Clinical data
Trade namesMefoxin, Renoxitin, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682737
License data
Pregnancy
category
  • AU: B1
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolismminimal
Elimination half-life41-59 min
Excretion85% urine
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.047.841 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O7S2
Molar mass427.45 g·mol−1
3D model (JSmol)
Melting point149 to 150 °C (300 to 302 °F) (dec.)
  • O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)Cc3sccc3)COC(=O)N)C(=O)O
  • 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.