cefoxitin
Trade name: mefoxin
Small moleculeapproved
Approved
Oct 18, 1978
Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria. The bactericidal action of cefoxitin results from inhibition of cell wall synthesis. — NCATS
Clinical trial activity
14 trials · 59 clinical orgs · 10 marketing orgs
Phase 1
1
Phase 2
3
Phase 3
3
Phase 4
2
Earliest trial started Feb 1, 2003 (NCT00343317)
Timeline
1970s
- Oct 18, 1978
Earliest FDA Approval
- Oct 18, 1978
Mylan — NDA Secondary Org
- Oct 18, 1978
PHARMOBEDIENT — Marketing Organization
1980s
- Jan 8, 1987
Mylan — Marketing Organization
2000s
- Jul 3, 2000
Fresenius — Marketing Organization
- Sep 11, 2000
West-Ward Pharmaceutical — Marketing Organization
- Jan 23, 2006
Hospira — Marketing Organization
- Mar 10, 2006
B. Braun — NDA Secondary Org
2010s
- Feb 26, 2010
Hikma — Marketing Organization
- Aug 31, 2011
ACS Dobfar — Marketing Organization
- Nov 16, 2015
Samson Medical — Marketing Organization
- Jan 1, 2017
Earliest Phase 3 Sponsor(trial)
- Jan 1, 2019
Earliest Phase 2 Sponsor(trial)
2020s
- Jan 1, 2025
Earliest Phase 1 Sponsor(trial)
Indications
Approved for
Studied for
- Antibiotic Prophylaxis · Phase 3
- Appendicitis · Phase 1
- Cesarean Section · Phase 2
- Colorectal Surgery · Phase 3
- Endometritis · Phase 2
- General Surgery · Phase 4
- Lung Diseases · Phase 2/Phase 3
- Pancreatic Diseases · Phase 3
- Pancreatic Neoplasms · Phase 3
- Urinary Tract Infections · Phase 4
- Wound Infection · Phase 2
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
- approvedPriority reviewOct 18, 1978
Chemistry & pharmacology
Loading structure…
SMILES
CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@@H]21- Mol. weight
- 427.46 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Prescription Only
Oral
No
Parenteral
Yes
Topical
No
Black box warning
Sources
- ChEMBLCHEMBL996 ↗
- WikipediaCefoxitin ↗
- NCATS6OEV9DX57Y ↗
- ChEMBLCHEMBL1200530 ↗
Also known as
- (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitin
- cefoxitina
- cefoxitina
- cefoxitine
- cefoxitine
- cefoxitin sodium
- cefoxitin sodium
- cefoxitin sodium
- cefoxitin sodium
- cefoxitin sodium salt
- cefoxitinum
- cefoxitinum
- ceftoxitin
- ceftoxitin
- cenomycin
- cenomycin
- cephoxitin
- cephoxitin
- cephoxitin
- cfx
- cfx
- mefoxin
- mefoxin
- mefoxin
- mefoxitin
- mefoxitin
- rephoxitin
- rephoxitin
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06860802 | Phase 1 | Feb 28, 2025 | Department of Health and Human Services, University of Michigan |
| NCT05755789 | Phase 3 | Jun 22, 2023 | University of Poitiers |
| NCT04310930 | Phase 2/Phase 3 (Phase 3) | Mar 31, 2020 | Cystic Fibrosis Foundation, Erasmus University Rotterdam, Government of Australia, Griffith University, James Cook University Hospital, Middlesbrough, UK, Monash University, Murdoch University, Newcastle University, South Australian Health and Medical Research Institute, University of Copenhagen, University of Manitoba, University of Melbourne, University of Paris, University of Queensland |
| NCT03960970 | Phase 2 | Aug 1, 2019 | St. Barnabas Medical Center, Livingston, NJ |
| NCT03306290 | N/A | Oct 30, 2017 | University of Lorraine |
| NCT03269994 | Phase 3 | Aug 28, 2017 | Advocate Illinois Masonic Medical Center, Albany Medical College, Allegiance Health, Baptist Memorial Health Care Corporation, Baylor Scott and White, East Carolina University, Emory University, Gundersen Health System, Hackensack University Medical Center, Harvard University, Icahn School of Medicine at Mount Sinai, Indiana University, Johns Hopkins University, Memorial Sloan-Kettering Cancer Center, Northwestern University, Ohio State University, Pennsylvania State University, Providence Health & Services, Rhode Island Hospital, Stony Brook University, Temple University, The Cleveland Clinic, The University of Texas, Dallas, Thomas Jefferson University, University of California, Davis, University of Chicago, University of Iowa, University of Ottawa, University of Utah, University of Wisconsin, Washington University in St. Louis, Yeshiva University |
| NCT02958059 | N/A | Dec 1, 2016 | Yonsei University |
| NCT02800785 | N/A | May 1, 2016 | Cancer Research Network, University of California, Los Angeles, University of Washington |
| NCT02474706 | Phase 4 | Mar 1, 2016 | University of Lorraine |
| NCT02703857 | Phase 4 | Feb 1, 2016 | University of Poitiers |
| NCT02985086 | N/A | Jul 1, 2013 | University of Lisbon |
| NCT01820793 | N/A | May 1, 2013 | University of Paris |
| NCT00186082 | N/A | Sep 1, 2003 | Stanford University |
| NCT00343317 | N/A | Feb 1, 2003 | Bristol-Myers Squibb, University of Kwa-Zulu Natal |
Showing 14 of 14 trials
Page 1 / 1
Organizations
Research & Development (59)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| University of Lorraine | Academic/Hospital | 2 | 2 | 2 | 2016 |
| University of Paris | Academic/Hospital | 2 | 1 | 2 | 2013 |
| University of Poitiers | Academic/Hospital | 2 | 2 | 2 | 2016 |
| Advocate Illinois Masonic Medical Center | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Albany Medical College | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Allegiance Health | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Baptist Memorial Health Care Corporation | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Baylor Scott and White | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Bristol-Myers Squibb | For profit | 1 | 0 | 1 | 2003 |
| Cancer Research Network | Academic/Hospital | 1 | 0 | 1 | 2016 |
| Cystic Fibrosis Foundation | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Department of Health and Human Services | Government | 1 | 0 | 1 | 2025 |
| East Carolina University | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Emory University | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Erasmus University Rotterdam | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Government of Australia | Government | 1 | 0 | 1 | 2020 |
| Griffith University | Academic/Hospital | 1 | 0 | 1 | 2020 |
| Gundersen Health System | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Hackensack University Medical Center | Academic/Hospital | 1 | 0 | 1 | 2017 |
| Harvard University | Academic/Hospital | 1 | 0 | 1 | 2017 |
59 organizations
Page 1 / 3
Marketing (13)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ACS Dobfar | For profit | SYN | Jun 12, 2009 |
| ACS Dobfar | For profit | MKTG | Aug 31, 2011 |
| B. Braun | For profit | NDA2 | Mar 10, 2006 |
| Fresenius | For profit | MKTG | Jul 3, 2000 |
| Hikma | For profit | MKTG | Feb 26, 2010 |
| Hikma | For profit | SYN | Sep 11, 2000 |
| Hospira | For profit | MKTG | Jan 23, 2006 |
| Merck | For profit | NDA | Feb 27, 1997 |
| Mylan | For profit | NDA2 | Oct 18, 1978 |
| Mylan | For profit | MKTG | Jan 8, 1987 |
| PHARMOBEDIENT | For profit | MKTG | Oct 18, 1978 |
| Samson Medical | For profit | MKTG | Nov 16, 2015 |
| West-Ward Pharmaceutical | For profit | MKTG | Sep 11, 2000 |