cefoperazone
Trade name: cefobid
Approved
Nov 18, 1982
Cefoperazone (marketed under the name Cefobid) is a third-generation cephalosporin antibiotic. Cefoperazone has a broad spectrum of activity: Respiratory Tract Infections caused by S. pneumoniae, H. influenzae, S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes (Group A beta-hemolytic streptococci), P. aeruginosa, Klebsiella pneumoniae, E. coli, Proteus mirabilis, and Enterobacter species. Peritonitis and Other Intra-abdominal Infections caused by E. coli, P. aeruginosa, and anaerobic gram-negative bacilli (including Bacteroides fragilis). Bacterial Septicemia caused by S. pneumoniae, S. agalactiae, S. aureus, Pseudomonas aeruginosa, E. coli, Klebsiella spp., Klebsiella pneumoniae, Proteus species (indole-positive and indole-negative), Clostridium spp. and anaerobic gram-positive cocci. Infections of the Skin and Skin Structures caused by S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes, and P. aeruginosa. Pelvic Inflammatory Disease, Endometritis, and Other Infections of the Female Genital Tract caused by N. gonorrhoeae, S. epidermidis, S. agalactiae, E. coli, Clostridium spp., Bacteroides species (including Bacteroides fragilis), and anaerobic gram-positive cocci. Cefobid has no activity against Chlamydia trachomatis. Therefore, when Cefobid is used in the treatment of patients with pelvic inflammatory disease and C. trachomatis is one of the suspected pathogens, appropriate anti-chlamydial coverage should be added. Urinary Tract Infections caused by Escherichia coli and Pseudomonas aeruginosa. Cefoperazone, a third-generation cephalosporin, interferes with cell wall synthesis by binding to the penicillin-binding proteins (PBPs), thus preventing cross-linking of nascent peptidoglycan. Cefoperazone is stable to penicillinases and has a high degree of stability to many beta-lactamases produced by gram-negative bacteria. When tested in vitro, cefoperazone has demonstrated synergistic interactions with aminoglycosides against gram-negative bacilli. As with all cephalosporins, hypersensitivity manifested by skin reactions or drug fever. Reversible neutropenia may occur with prolonged administration. Diarrhea or loose stools has been reported also. — NCATS
Clinical trial activity
10 trials · 12 clinical orgs · 1 marketing orgs
Earliest trial started Jul 1, 2004 (NCT00360607)
Timeline
Indications
Approved for
Studied for
- Abdominal Abscess · Phase 4
- Appendicitis · Phase 4
- Cholecystitis · Phase 4
- Communicable Diseases · Phase 4
- Esophageal Achalasia · Phase 3
- Infections · Phase 4
- Liver Cirrhosis, Biliary · Phase 4
- Pancreatitis, Acute Necrotizing · Phase 4
- Patient Compliance · Phase 4
- Peritonitis · Phase 4
- Pharmacology · Phase 4
- Pneumonia · Phase 1/Phase 2
- Respiratory Tract Infections · Phase 2
- Urinary Tract Infections · Phase 2
- Wound Infection · Phase 4
Mechanism of action
- Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor
- D-alanyl-D-alanine carboxypeptidase DacB (dacB) ↗
- Peptidoglycan D,D-transpeptidase FtsI (ftsI) ↗
- Penicillin-binding protein 1A (mrcA) ↗
- Penicillin-binding protein 1B (mrcB) ↗
- D-alanyl-D-alanine carboxypeptidase DacA (dacA) ↗
- Peptidoglycan D,D-transpeptidase MrdA (mrdA) ↗
- D-alanyl-D-alanine carboxypeptidase DacC (dacC) ↗
Approval history
- approvedNov 18, 1982
Chemistry & pharmacology
SMILES
CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(CSc4nnnn4C)CS[C@H]23)c2ccc(O)cc2)C(=O)C1=O- Mol. weight
- 645.68 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL507674 ↗
- WikipediaCefoperazone ↗
- NCATS7U75I1278D ↗
- ChEMBLCHEMBL1697715 ↗
- ChEMBLCHEMBL1200482 ↗
Also known as
- (6r,7r)-7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-7-((r)-2-(4-ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1h-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
- (6r,7r)-7-((r)-2-(4-ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1h-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
- biocefazon
- cefobid
- cefobid
- cefobid
- cefobid
- cefobis
- cefobis
- cefoperazine
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone
- cefoperazone dihydrate
- cefoperazone sodium
- cefoperazone sodium
- cefoperazone sodium
- cefoperazone sodium
- cefoperazono
- cefoperazono
- cefoperazonum
- cefoperazonum
- cephaperazon
- cp-526402
- cp-526402
- cp-52640-2
- cp-52640-2
- cp-75385-02
- t-1551
- t-1551
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT05925309 | N/A | Jul 1, 2023 | Fudan University |
| NCT05654090 | Phase 4 | Aug 25, 2022 | Yung Shin Pharm. Ind. Co., Ltd. |
| NCT05052619 | N/A | Jul 1, 2021 | Chinese Academy of Medical Sciences |
| NCT04370145 | Phase 4 | Jun 30, 2020 | Huazhong University of Science and Technology, Jiao Tong University |
| NCT03784365 | Phase 3 | Oct 1, 2018 | Asian Institute of Gastroenterology |
| NCT03436719 | N/A | Nov 6, 2017 | Government of Russia |
| NCT02060149 | Phase 1/Phase 2 (Phase 2) | Mar 1, 2014 | People's Liberation Army of China |
| NCT01992198 | Phase 4 | Jul 1, 2012 | Jiao Tong University, Shanghai Ruijin Hospital North |
| NCT01601093 | Phase 2 | Nov 1, 2011 | Nanjing Medical University, Xiangbei Welman Pharmaceutical Co., Ltd |
| NCT00360607 | Phase 4 | Jul 1, 2004 | Pfizer |
Organizations
Research & Development (12)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Jiao Tong University | Academic/Hospital | 2 | 0 | 1 | 2012 |
| Asian Institute of Gastroenterology | Academic/Hospital | 1 | 1 | 1 | 2018 |
| Chinese Academy of Medical Sciences | Academic/Hospital | 1 | 1 | 1 | 2021 |
| Fudan University | Academic/Hospital | 1 | 1 | 1 | 2023 |
| Government of Russia | Government | 1 | 1 | 1 | 2017 |
| Huazhong University of Science and Technology | Academic/Hospital | 1 | 1 | 1 | 2020 |
| Nanjing Medical University | Academic/Hospital | 1 | 0 | 1 | 2011 |
| People's Liberation Army of China | Government | 1 | 1 | 1 | 2014 |
| Pfizer | For profit | 1 | 1 | 1 | 2004 |
| Shanghai Ruijin Hospital North | Academic/Hospital | 1 | 1 | 1 | 2012 |
| Xiangbei Welman Pharmaceutical Co., Ltd | For profit | 1 | 1 | 1 | 2011 |
| Yung Shin Pharm. Ind. Co., Ltd. | For profit | 1 | 1 | 1 | 2022 |