Brand Name(s) in US
ChemicalBook > CAS DataBase List > Cefoxitin sodium

Cefoxitin sodium

Brand Name(s) in US
Product Name
Cefoxitin sodium
CAS No.
33564-30-6
Chemical Name
Cefoxitin sodium
Synonyms
MK-306;MERXIN;BETACEF;FARMOXIN;(6R,7S)-;CENOMYCIN;MEFOXITIN;Mefoxithin;CEFOXITIN NA;cefoxotinsodium
CBNumber
CB6495398
Molecular Formula
C16H18N3NaO7S2
Formula Weight
451.44
MOL File
33564-30-6.mol
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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 
Solid
color 
White
Water Solubility 
Soluble in water or methanol
InChI
InChI=1/C16H17N3O7S2.Na.H/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+;;/s3
InChIKey
GNWUOVJNSFPWDD-XMZRARIVSA-M
SMILES
N([C@@]1(C(=O)N2C(=C(COC(=O)N)CS[C@]12[H])C(=O)O)OC)C(=O)CC1SC=CC=1.[NaH] |&1:1,14,r|
CAS DataBase Reference
33564-30-6(CAS DataBase Reference)
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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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C4786
Product name
Cefoxitin sodium salt
Purity
analytical standard
Packaging
1g
Price
$372
Updated
2024/03/01
Sigma-Aldrich
Product number
C4786
Product name
Cefoxitin sodium salt
Purity
analytical standard
Packaging
5g
Price
$878
Updated
2024/03/01
TCI Chemical
Product number
C3602
Product name
Cefoxitin Sodium
Packaging
1G
Price
$135
Updated
2024/03/01
TCI Chemical
Product number
C3602
Product name
Cefoxitin Sodium
Packaging
5G
Price
$420
Updated
2021/12/16
Alfa Aesar
Product number
J66800
Product name
Cefoxitin sodium, 92.7-97%
Packaging
1g
Price
$189
Updated
2024/03/01
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Cefoxitin sodium Chemical Properties,Usage,Production

Brand Name(s) in US

Mefoxin

Description

Cefoxitin is a second generation cephalosporin antibiotic that has been used to treat a wide range of gram-negative and gram-positive bacteria including anaerobes. It acts by interfering with bacterial cell wall synthesis and has also been shown to induce β-lactamase synthesis.

Chemical Properties

Solid

Originator

Mefoxin,Merck Sharp and Dohme,US,1978

Uses

A broad spectrum antibiotic

Uses

An antibiotic derived from Cephamycin C.

Uses

Cefoxitin sodium can be used as semi-synthetic antibiotic derived from Cephamycin C, possessing high resistance to β-lactamase inactivation.

Definition

ChEBI: Cefoxitin sodium is an organic molecular entity.

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.

References

[1]. miller ak, celozzi e, kong y, et al. cefoxitin, a semisynthetic cephamycin antibiotic: in vivo evaluation. antimicrob agents chemother. 1974 jan;5(1):33-7.
[2]. jacoby ga. ampc beta-lactamases. clin microbiol rev.2009 jan;22(1):161-82.

Cefoxitin sodium Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Cefoxitin sodium manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cefoxitin sodium 33564-30-6
Price
US $0.00/KG/Tin
Min. Order
10KG
Purity
927-970μg/mg Sterile USP
Supply Ability
100kg
Release date
2021-08-06
Hebei Weibang Biotechnology Co., Ltd
Product
Cefoxitin sodium 33564-30-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10mt
Release date
2024-10-30
Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Cefoxitin sodium 33564-30-6
Price
US $0.00/Kg
Min. Order
1Kg
Purity
99%
Supply Ability
10kg
Release date
2024-04-09

33564-30-6, Cefoxitin sodiumRelated Search:

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  • 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
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  • 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)-
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  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,sodium salt (1:1), (6R,7S)-
  • (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-carboxylic acid, sodium salt
  • 33564-30-6
  • 156-1-41
  • 99-0-7
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  • C16H16N3O7S2Na
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