Cefoxitin

Cefoxitin

Systematic (IUPAC) name
(6S,7R)-4-(carbamoyloxymethyl)-7-methoxy- 8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia- 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Mefoxin
AHFS/Drugs.com	monograph
MedlinePlus	a682737
Pregnancy cat.	B
Legal status	?
Routes	IV
Pharmacokinetic data
Metabolism	minimal
Half-life	41-59 min
Excretion	85% urine
Identifiers
CAS number	35607-66-0 Y
ATC code	J01DC01
PubChem	CID 441199
DrugBank	DB01331
ChemSpider	389981 Y
UNII	6OEV9DX57Y Y
KEGG	D02345 N
ChEBI	CHEBI:209807 N
ChEMBL	CHEMBL996 N
Chemical data
Formula	C16H17N3O7S2
Mol. mass	427.454 g/mol
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 Y Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-N Y
N (what is this?)  (verify)

Cefoxitin is a cephamycin antibiotic developed by Merck & Co., Inc., often grouped with the second−generation cephalosporins. It is sold under the brand name 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 inhibitor, as are certain other antibiotics (such as imipenem).