Cefoxitin

Cefoxitin

Systematic (IUPAC) name
(6S,7R)-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
Clinical data
Trade names	Mefoxin
AHFS/Drugs.com	monograph
MedlinePlus	a682737
Pregnancy category	B
Routes of administration	IV
Pharmacokinetic data
Metabolism	minimal
Biological half-life	41-59 min
Excretion	85% urine
Identifiers
CAS Number	35607-66-0
ATC code	J01DC01 (WHO)
PubChem	CID 441199
DrugBank	DB01331
ChemSpider	389981
UNII	6OEV9DX57Y
KEGG	D02345
ChEBI	CHEBI:209807
ChEMBL	CHEMBL996
Chemical data
Formula	C16H17N3O7S2
Molar 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 Key:WZOZEZRFJCJXNZ-ZBFHGGJFSA-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 many strains of Enterobacter cloacae. Staphylococci resistant to methicillin/oxacillin should be considered resistant to cefoxitin.^[1]

Cefoxitin is considered to be a strong beta-lactamase inducer, as are certain other antibiotics (such as imipenem).^[2]

Spectrum of Bacterial Susceptibility

Cefoxitin has a broad spectrum of activity and has been used in the treatment of skin, bone, respiratory and urinary tract infections. Susceptible bacteria include some Staphylococci, Enterococci, Streptococci, and others. The following represents MIC susceptibility data for a few medically significant microorganisms.

• Escherichia coli: 0.2 μg/ml – 64 μg/ml
• Haemophilus influenzae: 0.5 μg/ml – 12.5 μg/ml
• Streptococcus pneumoniae: 0.2 μg/ml – 1 μg/ml

^[3]

References

1. Mefoxin Official FDA information at Drugs.com
2. Phillips I, Shannon K (1993). "Importance of beta-lactamase induction". Eur J Clin Microbiol Infect Dis. 12 Suppl 1: S19–26. PMID 8477758.
3. http://www.toku-e.com/Assets/MIC/Cefoxitin.pdf