cefoperazone

Trade name: cefobid

Small moleculeapproved

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

Phase 1
1
Phase 2
3
Phase 3
1
Phase 4
4

Earliest trial started Jul 1, 2004 (NCT00360607)

Timeline

1980s

  1. Nov 18, 1982

    Pfizer — Earliest FDA Approval

  2. Nov 18, 1982

    Pfizer — NDA Organization

1990s

  1. Mar 31, 1995

    Pfizer — Marketing Organization

2010s

  1. Jan 1, 2011

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2014

    Earliest Phase 1 Sponsor(trial)

  3. Jan 1, 2018

    Earliest Phase 3 Sponsor(trial)

Indications

Mechanism of action

Approval history

  • approvedNov 18, 1982

Chemistry & pharmacology

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT05925309N/AJul 1, 2023Fudan University
NCT05654090Phase 4Aug 25, 2022Yung Shin Pharm. Ind. Co., Ltd.
NCT05052619N/AJul 1, 2021Chinese Academy of Medical Sciences
NCT04370145Phase 4Jun 30, 2020Huazhong University of Science and Technology, Jiao Tong University
NCT03784365Phase 3Oct 1, 2018Asian Institute of Gastroenterology
NCT03436719N/ANov 6, 2017Government of Russia
NCT02060149Phase 1/Phase 2 (Phase 2)Mar 1, 2014People's Liberation Army of China
NCT01992198Phase 4Jul 1, 2012Jiao Tong University, Shanghai Ruijin Hospital North
NCT01601093Phase 2Nov 1, 2011Nanjing Medical University, Xiangbei Welman Pharmaceutical Co., Ltd
NCT00360607Phase 4Jul 1, 2004Pfizer
Showing 10 of 10 trials
Page 1 / 1

Organizations

Research & Development (12)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Jiao Tong UniversityAcademic/Hospital2012012
Asian Institute of GastroenterologyAcademic/Hospital1112018
Chinese Academy of Medical SciencesAcademic/Hospital1112021
Fudan UniversityAcademic/Hospital1112023
Government of RussiaGovernment1112017
Huazhong University of Science and TechnologyAcademic/Hospital1112020
Nanjing Medical UniversityAcademic/Hospital1012011
People's Liberation Army of ChinaGovernment1112014
PfizerFor profit1112004
Shanghai Ruijin Hospital NorthAcademic/Hospital1112012
Xiangbei Welman Pharmaceutical Co., LtdFor profit1112011
Yung Shin Pharm. Ind. Co., Ltd.For profit1112022
12 organizations
Page 1 / 1

Marketing (2)

OrganizationOrg typeRelationshipDate
PfizerFor profitNDANov 18, 1982
PfizerFor profitMKTGMar 31, 1995