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 (50 mg/mL).
| 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 for infected patients. 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 Georgopapadakou, N. H. Mechanisms of Action of Cephalosporin 3'-quinolone Esters, Carbamates, and Tertiary Amines in Escherichia Coli. Antimicrobial Agents and Chemotherapy. 37(3) 559-565 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):731-5 PMID 316988 |
