Cefoxitin sodium

Base Information

• Chemical Name: Cefoxitin sodium
• CAS No.: 33564-30-6
• Molecular Formula: C16H16N3NaO7S2
• Molecular Weight: 449.441
• Hs Code.: 29419000
• Mol file: 33564-30-6.mol

Synonyms:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,monosodium salt, (6R,7S)- (9CI);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)-;Betacef;Cefaxilin sodium;Cefoxitin sodium salt;Cenomycin;Farmoxin;MK 306;Mefoxin;Mefoxithin;Mefoxitin;Merxin;Monosodium cefoxitin;Serviflox;Sodium cefoxitin;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)-;

Chemical Property of Cefoxitin sodium

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 3.24E-30mmHg at 25°C
• Melting Point: >160°C
• Boiling Point: 843.4 °C at 760 mmHg
• Flash Point: 463.9 °C
• PSA: 204.63000
• LogP: -0.20700
• Storage Temp.: 2-8°C
• Solubility.: Very soluble in water, sparingly soluble in alcohol.
• Water Solubility.: Soluble in water or methanol

Purity/Quality:

99% ^*data from raw suppliers

Cefoxitin sodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Cefoxitin sodium

There total 8 articles about Cefoxitin sodium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

cefoxitin (35607-66-0) → cefoxitin sodium (33564-30-6)

Guidance literature:

With sodium lactate; In acetone; at 30 ℃; for 0.166667h; Reagent/catalyst;

Reference yield:

isocyanate de chlorosulfonyle (1189-71-5) + C15H16N2O6S2 → cefoxitin sodium (33564-30-6)

Guidance literature:

isocyanate de chlorosulfonyle; C₁₅H₁₆N₂O₆S₂; In tetrahydrofuran; at -40 - -37 ℃; for 0.75h;

With sodium lactate; In methanol; acetone; at 10 - 12 ℃; for 2h; Temperature;

Reference yield:

cephalothin (153-61-7) → cefoxitin sodium (33564-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: methanesulfonic acid; N-Bromosuccinimide / dichloromethane; methanol / 2 h / -20 °C

1.2: 2 h / 0 °C / pH 6.5

2.1: sodium hydroxide / methanol; water / pH 10

2.2: 25 °C

3.1: tetrahydrofuran / Cooling

4.1: sodium lactate / acetone / 0.17 h / 30 °C

With N-Bromosuccinimide; methanesulfonic acid; sodium lactate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

upstream raw materials:

cefoxitin

cephalothin

isocyanate de chlorosulfonyle

2-thienylacetic acid chloride

Refernces

• 1、 -. "Application of cefoxitin sodium pharmaceutical preparations in preoperative infection prevention for transvaginal hysterectomy, laparoscopic hysterectomy and cesarean section". . . Retrieved 2019/11/13.
• 2、 Ratcliffe,Christensen. "Total synthesis of β lactam antibiotics III. (±) cefoxitin". . p. 4653 - 4656. Retrieved 2007/10/10.