cefotetan
Trade name: cefotan
Approved
Dec 27, 1985
Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms. It is FDA approved for the treatment of urinary tract infection, lower respiratory tract infection, skin and skin structure infections, gynecologic infection, intra-abdominal infection, and bone and joint infection; and for prophylaxis of postoperative infection. The bactericidal action of cefotetan results from inhibition of cell wall synthesis. The methoxy group in the 7-alpha position provides cefotetan with a high degree of stability in the presence of beta-lactamases including both penicillinases and cephalosporinase of gram-negative bacteria. Common adverse reactions include diarrhea and nausea. As with other cephalosporins, high concentrations of cefotetan may interfere with measurement of serum and urine creatinine levels. — NCATS
Clinical trial activity
4 trials · 4 clinical orgs · 6 marketing orgs
Earliest trial started Apr 1, 2002 (NCT00090272)
Timeline
1980s
- Dec 27, 1985
Teligent Pharmaceuticals — Earliest FDA Approval
- Dec 27, 1985
Pharmaceutical Associates — Marketing Organization
- Dec 27, 1985
Teligent Pharmaceuticals — NDA Organization
- Dec 27, 1985
Teligent Pharmaceuticals — NDA Secondary Org
- Dec 27, 1985
Pharmaceutical Associates — NDA Secondary Org
1990s
- Apr 29, 1993
Teligent Pharmaceuticals — Marketing Organization
2000s
2010s
- Jan 1, 2010
Earliest Phase 2 Sponsor(trial)
- Oct 26, 2011
Hikma — Marketing Organization
- Oct 26, 2011
West-Ward Pharmaceutical — Marketing Organization
- Jan 1, 2014
Earliest Phase 1 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 27, 1985
Chemistry & pharmacology
SMILES
CO[C@@]1(NC(=O)C2SC(=C(C(N)=O)C(=O)O)S2)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21- Mol. weight
- 575.63 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Racemic Mixture
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Prescription Only
Oral
No
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL474579 ↗
- WikipediaCefotetan ↗
- NCATS48SPP0PA9Q ↗
- ChEMBLCHEMBL1201098 ↗
Also known as
- (6r,7s)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5- yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid
- (6r,7s)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5- yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid
- apacef
- cefotan
- cefotan
- cefotan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan
- cefotetan disodium
- cefotetan disodium
- cefotetan disodium
- cefotetan disodium
- cefotetan sodium
- cefotetan sodium
- cefotetanum
- cefotetanum
- ici-156834
- ici-156834
- yamatetan
- yamatetan
- ym-09330
- ym-09330
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT04726046 | Phase 1 | Apr 1, 2014 | Chonbuk National University |
| NCT01220661 | Phase 2 | Oct 1, 2010 | National Cancer Center, Korea |
| NCT00186082 | N/A | Sep 1, 2003 | Stanford University |
| NCT00090272 | Phase 3 | Apr 1, 2002 | Merck |
Organizations
Research & Development (4)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Chonbuk National University | Academic/Hospital | 1 | 1 | 1 | 2014 |
| Merck | For profit | 1 | 1 | 1 | 2002 |
| National Cancer Center, Korea | Government | 1 | 1 | 1 | 2010 |
| Stanford University | Academic/Hospital | 1 | 1 | 1 | 2003 |
Marketing (9)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| B. Braun | For profit | NDA2 | Aug 9, 2007 |
| Fresenius | For profit | MKTG | Aug 9, 2007 |
| Hikma | For profit | MKTG | Oct 26, 2011 |
| Pharmaceutical Associates | For profit | MKTG | Dec 27, 1985 |
| Pharmaceutical Associates | For profit | NDA2 | Dec 27, 1985 |
| Teligent Pharmaceuticals | For profit | NDA | Dec 27, 1985 |
| Teligent Pharmaceuticals | For profit | NDA2 | Dec 27, 1985 |
| Teligent Pharmaceuticals | For profit | MKTG | Apr 29, 1993 |
| West-Ward Pharmaceutical | For profit | MKTG | Oct 26, 2011 |