Cefpodoxime Proxetil is a broad-spectrum, third-generation, semi-synthetic cephalosporin β-lactam antibiotic. It is an esterified cephem antibiotic that is hydrolyzed and de-esterified in vivo to its active metabolite Cefpodoxime. Cefpodoxime was patened in 1980. The dissolution of Cefpodoxime Proxetil is pH dependent. Cefpodoxime Proxetil is soluble in DMSO.
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| Mechanism of Action | Like β-lactams, cephalosporins interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to cephalosporins is commonly due to cells containing plasmid encoded β-lactamases. However, like many cephalosporins, cefpodoxime is stable in the presence of β-lactamases. |
| Spectrum | Cefpodoxime Proxetil is a broad-spectrum antibiotic which targets a wide variety of Gram-positive and Gram-negative bacteria especially those which cause otitis media and pharyngitis. It has no activity against enterococci. |
| Impurity Profile | Impurity A| (6R,7R)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (cefpodoxime)|80210-62-4|C15H17N5O6S2|427.46| Impurity B| (1RS)-1-[[(1-methylethoxy)carbonyl]oxy]ethyl (6R,7R)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (ADCA-analogue of cefpodoxime proxetil)||C20H25N5O8S2|527.57| Impurity C| (1RS)-1-[[(1-methylethoxy)carbonyl]oxy]ethyl (6R,7R)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate (delta-2-cefpodoxime proxetil)||C21H27N5O9S2|557.59| Impurity D| (1RS)-1-[[(1-methylethoxy)carbonyl]oxy]ethyl (6R,7R)-7-[[(2E)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (anti-cefpodoxime proxetil)||C21H27N5O9S2|557.59| Impurity E| (1RS)-1-[[(1-methylethoxy)carbonyl]oxy]ethyl (6R,7R)-3-(acetoxymethyl)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (ACA-analogue of cefpodoxime proxetil)||C22H27N5O10S2|585.61| Impurity F| (1RS)-1-[[(1-methylethoxy)carbonyl]oxy]ethyl (6R,7R)-7-[[(2Z)-2-[(2-formylamino)thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (N-formyl cefpodoxime proxetil)||C22H27N5O10S2|585.61| Impurity G||||| Impurity H| mixture of the diastereoisomers of 1-[[(1-methylethoxy)carbonyl]oxy]ethyl (6R,7R)-7-[[(2Z)-2-[2-[[(2R)-2-[[(2Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl]amino]-2-[(2R)-5-(methoxymethyl)-4-[[1-[[(1-methylethoxy)carbonyl]oxy]ethoxy]carbonyl]-3,6-dihydro-2H-1,3-thiazin-2-yl]acetyl]amino]thiazol-4-yl]-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (cefpodoxime proxetil dimer||C43H52N10O19S4|1141.19| |
| Microbiology Applications | Cefpodoxime is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options.
For a representative list of Cefpodoxime MIC values, click here. |
| Molecular Formula | C21H27N5O9S2 |
| References |
Borin MT (1991) A review of the pharmacokinetics of Cefpodoxime Proxetil. Drugs. 42(3):13-21 Doan VP et al (2019) Levofloxacin versus Cefpodoxime for antibacterial prophylaxis in allogeneic stem cell transplantation. Biol. Blood Marrow Transplant. 25(8):1637-1641 Georgopapadakou NH (1992) Mechanisms of action of Cephalosporin 3'-quinolone esters, carbamates, and tertiary amines in Escherichia coli. Antimicrob. Agents and Chemother. 37(3):559-565 Todd WM (1994) Cefpodoxime Proxetil: A comprehensive review. Int. J. Antimicrob. Agents 4(1):37-62 Wise R, Andrews JM, Ashby JP and Thornber D (1990) The in-vitro activity of Cefpodoxime: A comparison with other oral cephalosporins. J. Antimicrob. Chemother. 25(4):541–550 PMID 2351624 Product References Cefpodoxime (TOKU-E) was used against Escherichia coli NDM isolates in microdilution MIC assays. "Characterization of Escherichia coli NDM isolates with decreased susceptibility to aztreonam/avibactam: Role of a novel insertion in PBP3." (Alm et al, 2015) Cefpodoxime (TOKU-E) was used as a reference compound when characterizing the extended-spectrum AmpC (ESAC) β-lactamase enzymes in "Activity of avibactam against Enterobacter cloacae producing an extended-spectrum class C β-lactamase enzyme" (Lahiri et al, 2014) |
| MIC | Bacteroides bivius| 0.25 － >64| 1492| Bacteroides disiens| 0.25 － >64| 1492| Bacteroides distasonis| 0.25 － >64| 1492| Bacteroides fragilis| 0.25 － >64| 1492| Bacteroides fragilis| 8 － 128| 401| Bacteroides fragilis (NCTC 9343)| 32 － ?| 401| Bacteroides ovatus| 0.25 － >64| 1492| Bacteroides thetaiotaomicron| 0.25 － >64| 1492| Bacteroides vulgatus| 0.25 － >64| 1492| Brucella abortus| 0.25 － ?| 1492| Brucella melitensis| 0.25 － ?| 1492| Brucella suis| 0.25 － ?| 1492| Burkholderia cepacia| 16 － >128| 600| Citrobacter amalonaticus| 16 － ?| 1481| Citrobacter amalonaticus (4026 + β-lactamase positive)| 8 － ?| 1481| Citrobacter braakii| >16 － ?| 1481| Citrobacter farmeri| 1 － >16| 1481| Citrobacter freundii| 0.5 － >128| 600| Citrobacter freundii| 4 － >16| 1481| Citrobacter freundii (3757 + β-lactamase positive)| 128 － ?| 1481| Citrobacter spp.| 16 － >16| 1481| Citrobacter werkmanii| >16 － ?| 1481| Clostridium difficile| 64 － >64| 1492| Clostridium histolyticum| 0.25 － 16| 1492| Clostridium sordellii| 0.25 － 16| 1492| Clostridium sporogenes| 0.25 － 16| 1492| Enterobacter aerogenes| 0.25 － >64| 1492| Enterobacter aerogenes| 1 － >16| 1481| Enterobacter aerogenes (3701 + β-lactamase positive)| 32 － ?| 1481| Enterobacter amnigenus| >16 － ?| 1481| Enterobacter asburiae| >16 － ?| 1481| Enterobacter cloacae| 0.03 － >64| 1492| Enterobacter cloacae| 0.125 － >128| 600| Enterobacter cloacae| 8 － >16| 1481| Enterobacter cloacae (22491)| 2 － ?| 386| Enterobacter cloacae (3146 + β-lactamase positive)| 64 － ?| 1481| Enterobacter cloacae (53 + β-lactamase positive)| 32 － ?| 1481| Enterobacter hormaechei| 8 － >16| 1481| Enterobacter intermedius| >16 － ?| 1481| Enterobacter sakazakii| 0.13 － 1| 1492| Enterobacter taylorae| >16 － ?| 1481| Enterobacteriaceae| 0.06 － 128| 401| Enterococci| 1 － 128| 401| Enterococcus faecalis| 1 － >128| 600| Enterococcus faecalis| >64 － ?| 1492| Enterococcus faecalis (ATCC 29212)| >32 － ?| 401| Enterococcus faecium| >64 － ?| 1492| Enterococcus faecium| 128 － >128| 600| Enterococcus liquefaciens| >64 － ?| 1492| Escherichia coli| 0.125 － 8| 600| Escherichia coli| 0.12 － 512| 946| Escherichia coli| ? － ?| 946| Escherichia coli (ampicillin-resistant + ceftazidime-resistant)| 16 － 32| 1492| Escherichia coli (ampicillin-resistant + ceftazidime-susceptible)| 0.13 － 0.25| 1492| Escherichia coli (ampicillin-susceptible)| 0.13 － 0.5| 1492| Escherichia coli (ATCC 25922)| 0.25 － ?| 401| Escherichia coli (ATCC 25922)| 0.5 － ?| 290| Escherichia coli (ATCC 35218)| 0.5 － ?| 290| Escherichia coli (NCTC 10418)| 0.25 － ?| 401| Escherichia coli (OC4075)| 1 － ?| 290| Escherichia coli (OC4087)| >128 － ?| 290| Escherichia coli (OC4136)| >128 － ?| 290| Escherichia coli (OC4138)| 32 － ?| 290| Escherichia coli (OC4227)| 8 － ?| 290| Escherichia coli (OC4229)| 16 － ?| 290| Escherichia coli (OC4249)| 64 － ?| 290| Escherichia coli (OC6028)| 64 － ?| 290| Escherichia coli (OC6042)| 128 － ?| 290| Escherichia coli (OC6043)| >128 － ?| 290| Escherichia coli (OC6044)| >128 － ?| 290| Haemolytic streptococci| 0.015 － 0.12| 401| Haemophilus influenzae| ≤0.03 － 1| 500| Haemophilus influenzae| 0.032 － 0.5| 600| Haemophilus influenzae (ampicillin-resistant)| 0.03 － 1| 1492| Haemophilus influenzae (ampicillin-susceptible)| 0.03 － 0.5| 1492| Haemophilus influenzae (ATCC 49247)| 0.5 － ?| 401| Haemophilus influenzae (ESBL)| <0.03 － 0.12| 84| Haemophilus influenzae (ESBL)| ≤0.03 － 0.5| 114| Haemophilus influenzae (ESBL)| <0.03 － 0.5| 84| Haemophilus influenzae (ESBL)| ≤0.03 － 0.5| 195| Haemophilus influenzae (NCTC 11931)| 0.12 － ?| 401| Haemophilus influenzae (non-ESBL)| ≤0.03 － 0.5| 195| Haemophilus influenzae (non-ESBL)| ≤0.03 － 0.5| 114| Haemophilus parainfluenzae| 0.06 － 0.13| 1492| Haemophilus spp.| 0.06 － 0.5| 401| Hafnia alvei| 16 － ?| 1481| Helicobacter pylori| 0.5 － 4| 1492| Klebsiella oxytoca (ceftazidime-resistant)| 2 － ?| 1492| Klebsiella oxytoca (ceftazidime-susceptible)| 0.06 － 2| 1492| Klebsiella pneumonia| 0.063 － 32| 600| Klebsiella pneumonia (ATCC 13883)| ≤0.12 － ?| 290| Klebsiella pneumonia (ATCC 700603)| 8 － ?| 290| Klebsiella pneumonia (OC4074)| 128 － ?| 290| Klebsiella pneumonia (OC4076)| 32 － ?| 290| Klebsiella pneumonia (OC4105)| 32 － ?| 290| Klebsiella pneumonia (OC4110)| >128 － ?| 290| Klebsiella pneumonia (OC4239)| 64 － ?| 290| Klebsiella pneumonia (OC4244)| >128 － ?| 290| Klebsiella pneumonia (OC4250)| >128 － ?| 290| Klebsiella pneumonia (OC5064)| >128 － ?| 290| Klebsiella pneumoniae (ceftazidime-resistant)| 8 － 64| 1492| Klebsiella pneumoniae (ceftazidime-susceptible)| 0.03 － 4| 1492| Klebsiella rhinoscleromatis| >16 － ?| 1481| Listeria innocua| 2 － >64| 1492| Listeria ivanovii| 2 － >64| 1492| Listeria monocytogenes| 2 － >64| 1492| Listeria seeligeri| 2 － >64| 1492| Listeria welshimeri| 2 － >64| 1492| Moraxella catarrhalis| 0.06 － 0.5| 1492| Moraxella catarrhalis| 0.06 － 2| 84| Moraxella catarrhalis| 0.06 － 2| 114| Moraxella catarrhalis| 0.06 － 4| 195| Moraxella catarrhalis| 0.063 － 2| 600| Moraxella catarrhalis| ? － ?| 403| Moraxella catarrhalis| ≤0.03 － >4| 500| Morganella morganii| 0.13 － 64| 1492| Morganella morganii| 0.125 － 64| 600| Morganella morganii| 8 － >16| 1481| Neisseria gonorrhoeae (penicillin-resistant)| 0.004 － 0.06| 1492| Neisseria gonorrhoeae (penicillin-susceptible)| 0.004 － 0.06| 1492| Neisseria spp.| 0.002 － 0.06| 401| Pneumococci| 0.03 － 4| 401| Proteus mirabilis| 0.06 － 0.13| 1492| Proteus mirabilis| 0.032 － 0.125| 600| Proteus mirabilis| <=0.25 － 4| 1481| Proteus mirabilis (3750 + β-lactamase positive)| 8 － ?| 1481| Proteus penneri| 16 － ?| 1481| Proteus penneri (1767 + β-lactamase positive)| 32 － ?| 1481| Proteus vulgaris| 0.06 － 0.5| 1492| Proteus vulgaris| 0.032 － 16| 600| Proteus vulgaris| <=0.25 － >16| 1481| Proteus vulgaris (1405 + β-lactamase positive)| 128 － ?| 1481| Proteus vulgaris (1699 + β-lactamase positive)| 128 － ?| 1481| Proteus vulgaris (1765 + β-lactamase positive)| >128 － ?| 1481| Proteus vulgaris (1781 + β-lactamase positive)| 1 － ?| 1481| Providencia rettgeri| ≤0.004 － 8| 600| Providencia rettgeri| ≤0.004 － 8| 600| Providencia rettgeri| 0.008 － 2| 1492| Providencia rettgeri| <=0.25 － 0.5| 1481| Providencia stuartii| 0.06 － 0.5| 1492| Providencia stuartii| <=0.25 － >16| 1481| Pseudomonas aeruginosa| >128 － ?| 600| Pseudomonas aeruginosa (ATCC 27853)| >128 － ?| 401| Pseudomonas aeruginosa (carbenicillin-resistant)| >64 － ?| 1492| Pseudomonas aeruginosa (carbenicillin-susceptible)| >64 － ?| 1492| Pseudomonas aeruginosa (NCTC 10662)| 128 － ?| 401| Pseudomonas cepacia| 4 － >64| 1492| Pseudomonas fluorescens| 8 － >64| 1492| Pseudomonas putida| 8 － >64| 1492| Pseudomonas spp.| 0.25 － 128| 401| Pseudomonas stutzeri| 8 － >64| 1492| Salmonella Agona| 0.13 － 0.5| 1492| Salmonella Brandenburg| 0.13 － 0.5| 1492| Salmonella Enteritidis| 0.13 － 0.5| 1492| Salmonella typhimurium| 0.13 － 0.5| 1492| Serratia fonticola| >16 － ?| 1481| Serratia liquefaciens| 0.25 － >64| 1492| Serratia marcescens| 0.5 － >128| 600| Serratia marcescens| 0.25 － >64| 1492| Serratia marcescens| 2 － >16| 1481| Serratia marcescens (167 + β-lactamase positive)| >128 － ?| 1481| Serratia marcescens (91 + β-lactamase positive)| >128 － ?| 1481| Serratia plymuthica| 8 － ?| 1481| Serratia rubidaea (3134 + β-lactamase positive)| 2 － ?| 1481| Serratia rubidaea (3139 + β-lactamase positive)| 4 － ?| 1481| Shigella boydii| 0.25 － 0.5| 1492| Shigella flexneri| 0.25 － 0.5| 1492| Shigella sonnei| 0.25 － 0.5| 1492| Staphylococci| 1 － 128| 401| Staphylococcus aureus (ATCC 25923)| 4 － ?| 401| Staphylococcus aureus (ATCC 29213)| 2 － ?| 401| Staphylococcus aureus (ATCC 6571)| 1 － ?| 401| Staphylococcus aureus (methicillin-resistant)| 16 － >64| 1492| Staphylococcus aureus (methicillin-resistant)| 1 － >128| 600| Staphylococcus aureus (oxacillin-susceptible)| ? － ?| 403| Staphylococcus epidermidis (methicillin-resistant)| 4 － >64| 1492| Staphylococcus epidermidis (methicillin-resistant)| 4 － >128| 600| Staphylococcus epidermidis (methicillin-susceptible)| 0.25 － 16| 600| Staphylococcus epidermidis (methicillin-susceptible)| 0.5 － 4| 1492| Staphylococcus haemolyticus (methicillin-resistant)| >64 － ?| 1492| Staphylococcus hominis| 0.5 － 2| 1492| Staphylococcus intermedius| ? － ?| 946| Staphylococcus pseudintermedius| 0.25 － 8| 1397| Staphylococcus simulans| 0.5 － 2| 1492| Staphylococcus warneri| 0.5 － 1| 1492| Stenotrophomonas maltophilia| >128 － ?| 600| Streptococci| ? － ?| 403| Streptococci (hemolytic + group A)| 0.008 － 0.5| 1492| Streptococci (hemolytic + group B)| 0.03 － 0.25| 1492| Streptococci (hemolytic + group C)| 0.015 － 0.03| 1492| Streptococci (hemolytic + group G)| 0.015 － 0.06| 1492| Streptococcus agalactiae| 0.032 － 0.063| 600| Streptococcus milleri (group)| 0.015 － 0.25| 1492| Streptococcus mitior| 0.015 － 0.13| 1492| Streptococcus pneumonia| ? － ?| 403| Streptococcus pneumonia (ATCC 49619)| 0.12 － ?| 401| Streptococcus pneumonia (ATCC 5303 parent)| 0.015 － ?| 287| Streptococcus pneumonia (ATCC 6303 parent)| 0.03 － ?| 287| Streptococcus pneumonia (pbp2x and pbp2b or pbp1a and pbp2x genes abnormal + penicillin)| 0.125 － 8| 121| Streptococcus pneumonia (pbp2x gene abnormal + penicillin-intermidiate)| 0.063 － 2| 121| Streptococcus pneumonia (pbpla, pbp2x, and pbp2b genes abnormal + penicillin-resistant)| 1 － 32| 121| Streptococcus pneumonia (penicillin-intermediate)| 0.05 － 2| 469| Streptococcus pneumonia (penicillin-intermediate)| ≤0.03 － >4| 114| Streptococcus pneumonia (penicillin-intermediate)| <0.03 － >4| 84| Streptococcus pneumonia (penicillin-intermediate)| ≤0.03 － >4| 195| Streptococcus pneumonia (penicillin-intermediate)| ? － ?| 418| Streptococcus pneumonia (penicillin-intermediate)| 0.12 － 4| 287| Streptococcus pneumonia (penicillin-resistant)| 0.063 － 16| 600| Streptococcus pneumonia (penicillin-resistant)| 1.861 － 8| 469| Streptococcus pneumonia (penicillin-resistant)| ≤0.03 － >4| 114| Streptococcus pneumonia (penicillin-resistant)| <0.03 － >4| 84| Streptococcus pneumonia (penicillin-resistant)| ≤0.03 － >4| 195| Streptococcus pneumonia (penicillin-susceptible)| ? － ?| 418| Streptococcus pneumonia (penicillin-susceptible)| ≤0.03 － 4| 114| Streptococcus pneumonia (penicillin-susceptible)| <0.03 － 4| 84| Streptococcus pneumonia (penicillin-susceptible)| ≤0.03 － 4| 195| Streptococcus pneumonia (penicillin-susceptible)| 0.016 － 0.5| 121| Streptococcus pneumonia (penicillin-susceptible)| 0.023 － 0.064| 469| Streptococcus pneumonia (penicillin-susceptible)| 0.008 － 1| 600| Streptococcus pneumonia (penicillin-susceptible)| 0.008 － 2| 287| Streptococcus pneumoniae (penicillin-susceptible)| 0.015 － 0.13| 1492| Streptococcus pyogenes| ≤0.004 － 2| 600| Xanthomonas maltophilia| >64 － ?| 1492| Yersinia enterocolitica| 0.5 － 2| 1492| |
