Cefoperazone Sodium is a third generation cephalosporin antibiotic. It is semi-synthetic, β-lactamase resistant, with broad-spectrum bactericidal activity. It is used to study drug-protein binding such as penicillin binding proteins. Cefoperazone A is the principal metabolite. Cefoperazone sodium is freely soluble in aqueous solution.
| 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. Cefoperazone however, is largely resistant to β-lactamases produced by resistant cells. |
| Spectrum | Cefoperazone is active against Gram-positive and Gram-negative bacteria (ie Pseudomonas aeruginosa). |
| Impurity Profile | Impurity A| (5aR,6R)-6-[[(2R)-2-[[(4-ethyl-2,3-dioxopiperazin-1-yl)-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-5a,6-dihydro-3H, 7H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(4H)-dione|73240-08-1|C23H23N5O8S|529.53| Impurity B| (6R,7R)-7-[[(2R)-2-[[(4-ethyl-2,3-dioxopiperazin-1-yl)-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(4-methyl-5-thioxo-4,5-dihydro-1H-tetrazol-1-yl)methyl]-8-oxo-5-thial-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|711590-76-4|C25H26N9O8S2|644.67| Impurity C| 1-methyl-1H-tetrazole-5-thiol;|69713-31-1|C2H4N4S|116.145| Impurity D| (6R,7R)-7-amino-8-oxo-3-[(1H-1,2,3-triazol-4-yl-sulphanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7-TACA)|37539-03-0|C10H11N5O3S2|313.356| Impurity E| 7ACA|957-68-6|C10H12N2O5S|272.28| Impurity F| (6R,7S)-7-[[(2R)-2-[[(4-ethyl-2,3-dioxopiperazine-1-yl)-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl]-8-oxo-5-thial-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|1315481-36-7|C25H26N9O8S2|644.67| |
| Microbiology Applications | Cefoperazone is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include:
Media SupplementsCefoperazone can be used as a selective agent in several types of isolation media: Campylobacter Blood-Free Selective Agar - CCDA Selective Supplement Campylobacter Agar - Campylobacter Selective Supplement (Karmali) Blood Free Campylobacter Agar - CDMN Selective Supplement Bolton Broth - Bolton Broth Selective Supplement Campylobacter Agar Base - Modified Karmali Selective Supplement Bolton Broth - Modified Bolton Broth Selective Supplement |
| Molecular Formula | C25H26N9NaO8S2 |
| References | Brogden RN et al (1981) Cefoperazone: A review of its in vitro antimicrobial activity, pharmacological properties and therapeutic efficacy. Drugs 22:423-460 PMD 6459224 Hinkle AM, LeBlanc BM, Bodey GP (1980) In vitro evaluation of Cefoperazone. Antimicrobial Agents Chemother. 17(3):423-427 PMID 6448578 Matsubara N, Minami S, Muraoka T, Saikawa I, Mitsuhashi S (1979) In vitro antibacterial activity of Cefoperazone (T-1551), a new semisynthetic cephalosporin. Antimicrob Agents Chemother. 16(6):731-735 PMID 316988 |
