Brand Name(s) in US
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Cefoxitin sodium

Brand Name(s) in US
Cefoxitin sodium Structure
Cefoxitin sodium
  • CAS No.33564-30-6
  • Chemical Name:Cefoxitin sodium
  • CBNumber:CB6495398
  • Molecular Formula:C16H18N3NaO7S2
  • Formula Weight:451.44
  • MOL File:33564-30-6.mol
Cefoxitin sodium Property
  • Melting point: :>160°C
  • Boiling point: :843℃
  • alpha  :25589nm +210° (c = 1 in methanol)
  • Flash point: :>110°(230°F)
  • storage temp.  :2-8°C
  • solubility  :Very soluble in water, sparingly soluble in alcohol.
  • form  :neat
  • Water Solubility  :Soluble in water or methanol
  • InChIKey :GNWUOVJNSFPWDD-XMZRARIVSA-M
  • CAS DataBase Reference :33564-30-6(CAS DataBase Reference)
  • FDA UNII :Q68050H03T
  • NCI Drug Dictionary :cefoxitin sodium
Safety
  • Hazard Codes  :Xn,Xi
  • Risk Statements  :36/37/38-42/43
  • Safety Statements  :22-26-36/37-36/37/39
  • RIDADR  :3077
  • WGK Germany  :3
  • RTECS  :XI0330500
  • HazardClass  :9
  • PackingGroup  :III
  • HS Code  :29419000
  • Toxicity :LD50 in mice, rats, dogs (g/kg): 5.10, 8.98, >10.0 i.v. (Takayama)
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H317
  • Precautionary statements P261-P280g-P302+P352a-P321-P333+P313-P501a-P280
Cefoxitin sodium Price More Price(14)
  • Brand: Sigma-Aldrich
  • Product number: C0688000
  • Product name : Cefoxitin sodium
  • Purity: European Pharmacopoeia (EP) Reference Standard
  • Packaging: 
  • Price: $190
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: Y0001496
  • Product name : Cefoxitin sodium for peak identification
  • Purity: European Pharmacopoeia (EP) Reference Standard
  • Packaging: 
  • Price: $190
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: C4786
  • Product name : Cefoxitin sodium salt
  • Purity: analytical standard
  • Packaging: 1g
  • Price: $219
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: C4786
  • Product name : Cefoxitin sodium salt
  • Purity: analytical standard
  • Packaging: 5g
  • Price: $700
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: C3602
  • Product name : Cefoxitin Sodium
  • Purity: 
  • Packaging: 5G
  • Price: $420
  • Updated: 2021/03/22
  • Buy: Buy

Cefoxitin sodium Chemical Properties,Usage,Production

  • Brand Name(s) in US Mefoxin
  • Chemical Properties Solid
  • Originator Mefoxin,Merck Sharp and Dohme,US,1978
  • Uses Cefoxitin sodium can be used as semi-synthetic antibiotic derived from Cephamycin C, possessing high resistance to β-lactamase inactivation.
  • Uses An antibiotic derived from Cephamycin C.
  • Manufacturing Process Benzhydryl 3-carbamoyloxymethyl-7α-hydroxy-7β-(2-thienylacetamido) decephalosporanate, 543 mg, is stirred in 15 ml dry DMSO. Sodium hydride, 24 mg (48 mg of a 50% suspension of NaH in mineral oi1, which has been washed with hexane to remove the oil), is added. When hydrogen evolution has ceased, 126 mg dimethyl sulfate is added. The solution is stirred for one hour at room temperature, diluted with 100 ml benzene and washed six times with water; the last wash is made to pH 8, if necessary, by adding sodium bicarbonate. The solution is dried over MgSO4, filtered and evaporated, leaving benzhydryl 3-carbamoyloxymethyl-7β-(2-thienylacetamido)-7α- methoxydecephalosporanate, which may be purified if desired by chromatography on silica gel, eluting with 25:1 chloroformethyl acetate.
    Other methylating agents may be used in place of methyl sulfate, e.g., an equimolar amount of methyl iodide, bromide or chloride, using the same conditions, or methyl trifluoromethylsulfonate or trimethyloxonium trinitrobenzenesulfonate. The solvent in the latter two reagents is dimethyl ether-HMPA 1:1, using a reaction temperature of -20°C warming later to 25°C. In each instance, the benzhydryl 3-carbamoyloxymethyl-7β-(2- thienylacetamido)-7α-methoxydecephalosporanate is obtained.
    Benzhydryl 3-carbamoyloxymethyl-7β-(2-thienylacetamido)-7α- methoxydecephalosporanate (300 mg) in 0.5 ml in anisole and 2.5 ml of trifluoroacetic acid is reacted for 15 minutes at 10°C. The resulting mixture is evaporated at reduced pressure and flushed twice with anisole. The residue is dissolved in methylene chloride and extracted with 5% sodium bicarbonate solution. The aqueous solution is adjusted to pH 1.8 with 5% phosphoric acid and extracted with ethyl acetate. The organic solution is dried and evaporated to yield the pure 3-carbamoyloxymethyl-7α-methoxy-7β-(2- thienylacetamido)decephalosporanic acid, MP 165°C to 167°C. This may then be converted to the sodium salt.
  • brand name Mefoxin (Merck).
  • Therapeutic Function Antibiotic
  • Clinical Use Cefoxitin (Mefoxin) is a semisynthetic derivative obtainedby modification of cephamycin C, a 7α-methoxy-substitutedcephalosporin isolated independently from variousStreptomyces by research groups in Japan and the UnitedStates. Although it is less potent than cephalothin againstGram-positive bacteria and cefamandole against most of theEnterobacteriaceae, cefoxitin is effective against certainstrains of Gram-negative bacilli (e.g., E. coli, K. pneumoniae,Providencia spp., S. marcescens, indole-positiveProteus spp., and Bacteroides spp.) that are resistant to thesecephalosporins. It is also effective against penicillin-resistantS. aureus and N. gonorrhoeae. The activity of cefoxitin and cephamycins, in general,against resistant bacterial strains is because of their resistanceto hydrolysis by β-lactamases conferred by the 7α-methoxylsubstituent. Cefoxitin is a potent competitive inhibitor ofmany β-lactamases. It is also a potent inducer of chromosomallymediated β-lactamases. The temptation to exploit the β-lactamase–inhibiting properties of cefoxitin by combining itwith β-lactamase–labile β-lactam antibiotics should be temperedby the possibility of antagonism. In fact, cefoxitin antagonizesthe action of cefamandole against E. cloacae andthat of carbenicillin against P. aeruginosa. Cefoxitin aloneis essentially ineffective against these organisms.
    The pharmacokinetic properties of cefoxitin resemblethose of cefamandole. Because its half-life is relativelyshort, cefoxitin must be administered 3 or 4 times daily.Solutions of the sodium salt intended for parenteral administrationare stable for 24 hours at room temperature and 1week if refrigerated. 7α-Methoxyl substitution stabilizes, tosome extent, the β-lactam to alkaline hydrolysis.The principal role of cefoxitin in therapy seems to be forthe treatment of certain anaerobic and mixed aerobic–anaerobicinfections. It is also used to treat gonorrhea caused byβ-lactamase–producing strains. It is classified as a secondgenerationagent because of its spectrum of activity.
  • Veterinary Drugs and Treatments In the United States, there are no cefoxitin products approved for veterinary species, but it has been used clinically in several species when an injectable second generation cephalosporin may be indicated.
Cefoxitin sodium Preparation Products And Raw materials
Raw materials
Preparation Products
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33564-30-6, Cefoxitin sodiumRelated Search:
  • Sodium (6R,7S)-3-[(Carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • sodium 3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • MK-306
  • sodium (6r-cis)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • cefoxotinsodium
  • monosodiumcefoxitin
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  • FARMOXIN
  • CENOMYCIN
  • CEFOXITIN NA
  • CEFOXITIN SODIUM
  • CEFOXITIN SODIUM SALT
  • BETACEF
  • MERXIN
  • MEFOXITIN
  • (6r-cis)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • MK-306, Betacef, Cenomycin, Farmoxin, Mefoxin, Mefoxitin, Merxin,
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, monosodium salt, (6R,7S)-
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, monosodium salt, (6R-cis)-
  • Cefaxilin sodium
  • Mefoxithin
  • Cefoxitin Sodium(Sterile)
  • (6R,7S)-
  • Cefoxitin sodium for peak identification
  • Cefoxitin sodium salt, Antibiotic for Culture Media Use Only
  • Cefoxitin,Mefoxin,Cefoxitin Sodium,Cenomycin,MK-306
  • Cefoxitin sodium salt (Sterile)
  • (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 Sodium Salt
  • Cefoxitin for peak identification CRS
  • Cefoxitin sodium CRS
  • CefoxitinSodiumSal
  • Cefoxitin sodium USP/EP/BP
  • CEFOXITIN SODIUM INJECTABLE GRADE
  • 33564-30-6
  • 156-1-41
  • 99-0-7
  • 33564-33-6
  • C16H16N3O7S2Na
  • C16H16N3NaO7S2
  • C16H17N3NaO7S2
  • C16H17N3O7S2Na
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