cefmetazole
Trade name: zefazone
Approved
Dec 11, 1989
Cefmetazole is a semisynthetic cephamycin antibiotic. It has a broad spectrum of activity comparable to that of the second-generation cephalosporins, covering gram-positive, gram-negative, and anaerobic bacteria. Its bactericidal action results from inhibition of cell wall synthesis. It effectively treats abdominal and respiratory tract infections, pelvic inflammatory disease, urinary tract infections, skin and soft tissue infections and used for surgical prophylaxis, reducing or eliminating signs and symptoms of infection. Cefmetazole has a low frequency of adverse effects, and a side effect profile similar to that of other cephamycins. Adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions. — NCATS
Clinical trial activity
3 trials · 4 clinical orgs · 1 marketing orgs
Earliest trial started May 1, 2004 (NCT00292708)
Timeline
1980s
- Dec 11, 1989
Pharmacia & Upjohn — Earliest FDA Approval
- Dec 11, 1989
Pharmacia & Upjohn — NDA Organization
- Dec 11, 1989
Pharmacia & Upjohn — NDA Secondary Org
2000s
- Jan 1, 2004
Earliest Phase 3 Sponsor(trial)
Indications
Approved for
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
- approvedDec 11, 1989
Chemistry & pharmacology
SMILES
CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21- Mol. weight
- 471.55 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1201195 ↗
- WikipediaCefmetazole ↗
- NCATS3J962UJT8H ↗
- ChEMBLCHEMBL1201118 ↗
Also known as
- (6r,7s)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7s)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole
- cefmetazole sodium
- cefmetazole sodium
- cefmetazole sodium
- cefmetazole sodium
- cefmetazole sodium
- cefmetazole sodium
- cefmetazole sodium
- cefmetazole sodium salt
- cefmetazolo
- cefmetazolo
- cefmetazolum
- cefmetazolum
- u-72791
- u-72791
- u-72791a
- u-72791a
- zefazone
- zefazone
- zefazone
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT01112436 | Phase 4 | May 1, 2010 | Chung-Ang University |
| NCT00508690 | Phase 3 | Sep 1, 2007 | Japan Multinational Trial Organization, National Hospital Organization Kyoto Medical Center |
| NCT00292708 | Phase 3 | May 1, 2004 | National Cancer Center, Japan |
Organizations
Research & Development (4)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Chung-Ang University | Academic/Hospital | 1 | 1 | 1 | 2010 |
| Japan Multinational Trial Organization | Academic/Hospital | 1 | 1 | 1 | 2007 |
| National Cancer Center, Japan | Academic/Hospital | 1 | 1 | 1 | 2004 |
| National Hospital Organization Kyoto Medical Center | Academic/Hospital | 1 | 0 | 1 | 2007 |
Marketing (2)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Pharmacia & Upjohn | For profit | NDA | Dec 11, 1989 |
| Pharmacia & Upjohn | For profit | NDA2 | Dec 11, 1989 |