Cefoxitin

Cefoxitin
Clinical data
Trade names	Mefoxin, Renoxitin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682737
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: ℞-only;
Pharmacokinetic data
Metabolism	minimal
Elimination half-life	41-59 min
Excretion	85% 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 ;
PubChem CID	441199;
DrugBank	DB01331 ;
ChemSpider	389981 ;
UNII	6OEV9DX57Y;
KEGG	D02345 ; as salt: D00913 ;
ChEBI	CHEBI:209807 ;
ChEMBL	ChEMBL996 ;
CompTox Dashboard (EPA)	DTXSID1022764 ;
ECHA InfoCard	100.047.841
Chemical and physical data
Formula	C16H17N3O7S2
Molar mass	427.45 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	149 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 ; Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N ;
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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 was synthesized in order to create an antibiotic with a broader spectrum.^[3] It is often grouped with the second-generation cephalosporins.^[4] 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.^[5]^[6]

^ "Cefoxitin International". Drugs.com. 2 November 2020. Retrieved 8 November 2020.
^ Cite error: The named reference Cefoxitin FDA label was invoked but never defined (see the help page).
^ 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.
^ Levy SB (2013-11-11). The Antibiotic Paradox: How Miracle Drugs Are Destroying the Miracle. Springer. ISBN 978-1-4899-6042-9.
^ "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Archived from the original on November 1, 2021. Retrieved 2017-05-04.
^ "Supplement Approval" (PDF). Food and Drug Administration. Department of Health and Human Services. Archived from the original (PDF) on February 17, 2017.

[1] "Cefoxitin International". Drugs.com. 2 November 2020. Retrieved 8 November 2020.

[Cefoxitin_FDA_label-2] Cite error: The named reference Cefoxitin FDA label was invoked but never defined (see the help page).

[3] 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.

[4] Levy SB (2013-11-11). The Antibiotic Paradox: How Miracle Drugs Are Destroying the Miracle. Springer. ISBN 978-1-4899-6042-9.

[5] "Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations". www.accessdata.fda.gov. Archived from the original on November 1, 2021. Retrieved 2017-05-04.

[6] "Supplement Approval" (PDF). Food and Drug Administration. Department of Health and Human Services. Archived from the original (PDF) on February 17, 2017.

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