Cefoxitin

Title: Cefoxitin
CAS Registry Number: 35607-66-0
CAS Name: (6R,7S)-3-[[(Aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 3-(hydroxymethyl)-7-methoxy-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid carbamate (ester); 3-carbamoyloxymethyl-7a-methoxy-7-[2-(2-thienyl)acetamido]-3-cephem-4-carboxylic acid
Molecular Formula: C16H17N3O7S2
Molecular Weight: 427.45
Percent Composition: C 44.96%, H 4.01%, N 9.83%, O 26.20%, S 15.00%
Literature References: Semi-synthetic antibiotic derived from cephamycin C, q.v., possessing high resistance to b-lactamase inactivation. Synthesis: B. G. Christensen et al., DE 2129675; DE 2203653; eidem, US 4297488 (1971, 1972, 1981 all to Merck & Co.); Karady et al., J. Am. Chem. Soc. 94, 1410 (1972); Ratcliffe, Christensen, Tetrahedron Lett. 1973, 4653. Biological evaluation: Wallick, Hendlin, Antimicrob. Agents Chemother. 5, 25 (1974); Miller et al., ibid. 33; Onishi et al., ibid. 38; Hamilton, Miller et al., J. Antibiot. 27, 42 (1974). Mode of action: Onishi et al., Ann. N.Y. Acad. Sci. 235, 406 (1974). Toxicity: S. Takayama et al., Chemotherapy (Tokyo) 26, Suppl. 1, 150 (1978). Comprehensive reviews: J. Antimicrob. Chemother. 4, Suppl. B, 1-256 (1978); R. N. Brogden et al., Drugs 17, 1-37 (1979); E. O. Stapley, K. R. Brown, in Pharmacological and Biochemical Properties of Drug Substances vol. 3, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1981) pp 262-290. Comprehensive description: G. S. Brenner, Anal. Profiles Drug Subs. 11, 169-195 (1982). Symposium on therapeutic use in anaerobic and aerobic infectons: Hosp. Pract. 25, Suppl. 4, 1-56 (1990).
Properties: Crystals, mp 149-150° (dec). pKa 2.2. Very sol in acetone; sol in aq NaHCO3; very slightly sol in water. Practically insol in ether and chloroform.
Melting point: mp 149-150° (dec)
pKa: pKa 2.2
Derivative Type: Sodium salt
CAS Registry Number: 33564-30-6
Manufacturers' Codes: MK-306
Trademarks: Betacef (Firma); Farmoxin (Erba); Mefoxin (Merck & Co.); Mefoxitin (Merck & Co.); Cenomycin (Daiichi)
Molecular Formula: C16H16N3NaO7S2
Molecular Weight: 449.43
Percent Composition: C 42.76%, H 3.59%, N 9.35%, Na 5.12%, O 24.92%, S 14.27%
Properties: White crystals with characteristic odor. [a]25589nm +210° (c = 1 in methanol). Very sol in water; sol in methanol; sparingly sol in ethanol and acetone. Insol in aromatic and aliphatic hydrocarbons. LD50 in mice, rats, dogs (g/kg): 5.10, 8.98, >10.0 i.v. (Takayama).
Optical Rotation: [a]25589nm +210° (c = 1 in methanol)
Toxicity data: LD50 in mice, rats, dogs (g/kg): 5.10, 8.98, >10.0 i.v. (Takayama)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephamycins.
Cefozopran Cefpimizole Cefpiramide Cefpirome Cefpodoxime Proxetil

Cefoxitin
Cefoxitin.svg
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 YesY
ATC code J01DC01
PubChem CID 441199
DrugBank DB01331
ChemSpider 389981 YesY
UNII 6OEV9DX57Y YesY
KEGG D02345 N
ChEBI CHEBI:209807 N
ChEMBL CHEMBL996 N
Chemical data
Formula C16H17N3O7S2 
Mol. mass 427.454 g/mol
 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.