Cefpodoxime Proxetil (Doxef; CS-807; U-76252;) is a broad spectrum antibacterial agent that acts by binding to penicillin binding proteins (PBPs), thus inhibiting peptidoglycan synthesis, leading to disruption of bacterial cell wall biosynthesis. It is an ester prodrug of the active free acid metabolite Cefpodoxime, and is active against most Gram-positive and Gram-negative organisms. Cefpodoxime Proxetil has been widely used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea.
Physicochemical Properties
| Molecular Formula | C21H27N5O9S2 |
| Molecular Weight | 557.6 |
| Exact Mass | 557.125 |
| Elemental Analysis | C, 45.23; H, 4.88; N, 12.56; O, 25.82; S, 11.50 |
| CAS # | 87239-81-4 |
| Related CAS # | 80210-62-4 (free acid);82619-04-3 (sodium);87239-81-4 (Proxetil);79287-88-0 (HCl); 82623-37-8 (TFA); |
| PubChem CID | 6526396 |
| Appearance | White to light yellow solid powder |
| Density | 1.6±0.1 g/cm3 |
| Melting Point | 111-113°C |
| Index of Refraction | 1.671 |
| LogP | 2.17 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 13 |
| Heavy Atom Count | 37 |
| Complexity | 976 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C(C1=C(COC)CS[C@@H]2[C@@H](C(N12)=O)NC(=O)/C(/C1=CSC(N)=N1)=N\OC)(=O)OC(C)OC(=O)OC(C)C |
| InChi Key | LTINZAODLRIQIX-ZFEISNGRSA-N |
| InChi Code | InChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13+/t10?,14-,18-/m1/s1 |
| Chemical Name | 1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate |
| Synonyms | Banan Vantin Cefpodoxime ProxetilCS-807 Doxef U 76252Doxef CS 807 Toraximcephalosporin 807 CS 807 U-76,252 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References | Drug Dev Ind Pharm. 2021 Aug;47(8):1261-1278. |
| Additional Infomation |
Cefpodoxime proxetil is 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, pharyngitis, and sinusitis. It has a role as a prodrug and an antibacterial drug. It is a carboxylic ester, a cephalosporin and a carboxylic acid. It is functionally related to a cefpodoxime and a 4-{((R)-2-Carboxy-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7-ylcarbamoyl)-[(Z)-methoxyimino]-methyl}-thiazol-2-yl-ammonium. Vantin has been reported in Apis cerana with data available. Cefpodoxime Proxetil is a third generation semi-synthetic cephalosporin and a beta-lactam antibiotic with bactericidal activity. Cefpodoxime's effect is dependent on its binding to penicillin-binding proteins (PBPs) located in the bacterial cytoplasmic membrane. Binding results in the inhibition of the transpeptidase enzymes, thereby preventing cross-linking of the pentaglycine bridge with the fourth residue of the pentapeptide and interrupting consequent synthesis of peptidoglycan chains. As a result, cefpodoxime inhibits bacterial septum and cell wall synthesis formation. A prodrug of its active metabolite CEFPODOXIME. See also: Cefpodoxime (has active moiety). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~125 mg/mL (~224.18 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (3.73 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7934 mL | 8.9670 mL | 17.9340 mL | |
| 5 mM | 0.3587 mL | 1.7934 mL | 3.5868 mL | |
| 10 mM | 0.1793 mL | 0.8967 mL | 1.7934 mL |