Pipemidic acid is a pyridopyrimidine antibiotic similar in structure and mechanism to quinolone antibiotics. Pipemidic acid is slightly soluble in aqueous solution.
| Mechanism of Action | Pipemidic acid targets bacterial DNA gyrase, an enzyme which reduces DNA strain during replication. Because DNA gyrase is required during DNA replication, subsequent DNA synthesis and ultimately cell division is inhibited. |
| Spectrum | Pipemidic acid is a broad spectrum antibiotic covering a wide range of susceptible bacteria. |
| Impurity Profile | Impurity A| 8-ethyl-2-hydroxy-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid|||| Impurity B| 8-ethyl-2-methoxy-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid|||| Impurity C| 2-ethoxy-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid|||| Impurity D| ethyl 2-chloro-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate|||| Impurity E| ethyl 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate|||| Impurity F| 2-(4-acetylpiperazin-1-yl)-8-ethyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid (acetylpipemidic acid)|||| |
| Microbiology Applications | Pipemidic acid 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 infected patients. Representative MIC values include:
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| Molecular Formula | C14H17N5O3 |
| Solubility | Acids and Bases: Soluble Alcohols: Very slightly soluble Water: Very slightly soluble |
| References | Katae, Hiromi, and Akira Minami. "Pipemidic Acid, a New Antibacterial Agent Active Against Pseudomonas Aeruginosa: In Vitro Properties." Antimicrobial Agents and Chemotherapy 8.32 (1975): 132-38. www.ncbi.gov. 24 Mar. 1975. Web. 21 Aug. 2012. |
| MIC | Bacillus subtilis| 3.13|| Bacteroides bivius| 25|| Bacteroides distasonis| 100|| Bacteroides fragilis| 200|| Bacteroides gracilis| 6.25|| Bacteroides intermedius| 25|| Bacteroides oralis | 12.5|| Bacteroides oris| 25|| Bacteroides ovatus| 200|| Bacteroides thetaiotaomicron| 200|| Bacteroides uniformis| 100|| Bacteroides ureolyticus| 6.25|| Bacteroides vulgatus| 100|| Bifidobacterium adolescentis| ≤0.025|| Capnocytophaga ochracea | ≤0.025|| Clostridium difficile| >200|| Clostridium perfringens| 25|| Clostridium septicum| 12.5|| Enterobacter aerogenes| 1.56|| Enterobacter cloacae| 1.56|| Escherichia coli| 0.78 - 1.56|| Eubacterium lentum| 50|| Fusobacterium mortiferum| 100|| Fusobacterium varium| 200|| Klebsiella pneumoniae| 1.56|| Peptostreptococcus anaerobius| 50|| Peptostreptococcus asaccharolyticus| 50|| Peptostreptococcus magnus| 100|| Peptostreptococcus prevotii| 50|| Proteus mirabilis| 6.25|| Proteus morganii| 1.56|| Proteus rettgeri| 1.56|| Proteus spp.| 1.57 - 2.25|| Proteus vulgaris| 1.56|| Pseudomonas aeruginosa| 3.13 - 50|| Salmonella Enteritidis| 1.56|| Salmonella Paratyphi| 0.78|| Salmonella schottmulleri| 0.78|| Salmonella typhimurium| 1.56|| Serratia marcescens| 1.56 - 3.13|| Staphylococcus asaccharolyticus| 25|| Staphylococcus aureus| 6.25 - 50|| Streptococcus intermedius| 200|| Streptococcus pyogenes| 61 - >100|| Veillonella parvula | 25|| |
