Basic information Brand Name(s) in US Safety Related Supplier
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Cefpodoxime proxetil

Basic information Brand Name(s) in US Safety Related Supplier
Cefpodoxime proxetil Basic information
Cefpodoxime proxetil Chemical Properties
  • Melting point:111-113°C
  • Density 1.58±0.1 g/cm3(Predicted)
  • RTECS XI0367370
  • storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
  • solubility Soluble in DMSO
  • pka8.13±0.60(Predicted)
  • form neat
  • Sensitive Light Sensitive
  • InChIKeyLTINZAODLRIQIX-FBXRGJNPSA-N
  • CAS DataBase Reference87239-81-4(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38-42/43
  • Safety Statements 22-26-36/37/39
  • WGK Germany 3
  • HS Code 30042000
  • ToxicityLD50 in male, female mice, male, female rats (mg/kg): >10000, >10000, >2000, >2000 s.c., 3502, 2535, >4000, >4000 i.p.; >8000, >8000, >4000, >4000 orally (Nakao, 1988)
Cefpodoxime proxetil Usage And Synthesis
  • Brand Name(s) in USSimplicef (veterinary drug)
    Vantin (human drug)
  • DescriptionCefpodoxime proxetil is an orally active, broad-spectrum cephalosporin especially useful in the treatment of bacterial infections in children. It is a prodrug converted by esterases in the GI walls to cefpodoxime, which reportedly has a bacteriostatic spectrum comparable to injectable third-generation cephem antibiotics.
  • Chemical PropertiesPale Yellow Solid
  • OriginatorSankyo (Japan)
  • UsesA metabolite of Cefpodoxime Proxetil. An antibacterial.
  • UsesAn antibacterial. A broad spectrum, orally absorbed third generation cephalosporin, ester prodrug of the active free acid metabolite, Cefpodoxime
  • DefinitionChEBI: The 1-[(isopropoxycarbonyl)oxy]ethyl (proxetil) ester prodrug of cefpodoxime. After swallowing, hydrolysis of the ester group occurs in the intestinal epithelium, to release active cefpodoxime in the bloodstream. It is used to treat acute otitis media, pha yngitis, and sinusitis.
  • Manufacturing ProcessA suspension of 30 g of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid in 300 ml acetone is mixed with 18.6 g 1,8-diazabicyclo[5.4.0]undec-7- ene. The solution obtained mixed at ca. 0°C with 261 g of a 14% toluene solution of 1-iodoethylisopropyl carbonate. After 4 hours the solution is poured onto a mixture of 600 ml of water and 21 ml conc. HCl. The pH of mixture is adjusted to ca. 1.0. The aqueous phase is extracted with 200 ml of hexane, mixed with 700 ml ethyl acetate and pH is adjusted to ca. 8.2. A solution of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid 1- (isopropoxycarbonyloxy)ethyl ester is obtained. Diastereoisomeric ratio B/(A+B)=0.49 (B is more apolar of the two diastereoisomers).
    To a solution of 37.4 g of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid 1-(isopropoxycarbonyloxy)ethyl ester in 689 ml ethyl acetate at 2-3°C is added for 25 min 0.105 moles Z-(2-formamidothiazol-4-yl)-methoxy-acetyl chloride hydrochloride. After 25 min pH is adjusted to ca. 6.5-7.3. After 1 hour the organic layer is washed with water and concentrated. It was obtained a crude 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2- amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl ester, (6R,7R)- (Cefpodoxime proxetil). Diastereoisomeric ratio 0.49.
    For purification 5 g of cefpodoxime proxetil are added to a mixture of 35 ml of methanol and 0.6 ml conc. H2SO4. The mixture is stirred for 90 min and slowly added during 25 min to a mixture of 2.1 g sodium bicarbonate and 400 ml water. The suspension obtained is stirred for 1 hour and the precipitate is isolated through a suction filter, washed with water and dried over phosphorus pentoxide at 35°C in a vacuum. 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)- 3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl ester, (6R,7R)-; (Cefpodoxime proxetil) is obtained in a diastereoisomeric ratio 0.528.
  • brand nameVantin (Pharmacia & Upjohn);Banan.
  • Therapeutic FunctionAntibiotic
  • Clinical UseCefpodoxime proxetil (Vantin) is the isopropyloxycarbonylethylester of the third-generation cephalosporincefpodoxime. This orally active prodrug derivative is hydrolyzedby esterases in the intestinal wall and in theplasma to provide cefpodoxime. Tablets and a powder forthe preparation of an aqueous suspension for oral pediatricadministration are available. The oral bioavailability of cefpodoximefrom the proxetil is estimated to be about 50%.Administration of the prodrug with food enhances its absorption.The plasma half-life is 2.2 hours, which permitsadministration on a twice-daily schedule.
    Cefpodoxime is a broad-spectrum cephalosporin withuseful activity against a relatively wide range of Grampositiveand Gram-negative bacteria. It is also resistant tomany β-lactamases. Its spectrum of activity includes S.pneumoniae, Streptococcus pyogenes, S. aureus, H. influenzae,M. catarrhalis, and Neisseria spp. Cefpodoxime is alsoactive against members of the Enterobacteriaceae family,including E. coli, K. pneumoniae, and P. mirabilis. It thusfinds use in the treatment of upper and lower respiratory infections,such as pharyngitis, bronchitis, otitis media, andcommunity-acquired pneumonia. It is also useful for thetreatment of uncomplicated gonorrhea.
  • Veterinary Drugs and TreatmentsIn dogs, cefpodoxime is indicated for the treatment of skin infections caused by Staphylococcus intermedius, Staphylococcus aureus, Streptococcus canis, E. coli, Proteus mirabilis, and Pasteurella multocida. Although not currently approved for cats, it may also be useful as well.
Cefpodoxime proxetil Preparation Products And Raw materials
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