cefuroxime
Trade name: zinacef
Approved
Oct 19, 1983
Cefuroxime is a semisynthetic, broad-spectrum, cephalosporin antibiotic. Cefuroxime is a bactericidal agent that acts by inhibition of bacterial cell wall synthesis. Cefuroxime has activity in the presence of some beta-lactamases, both penicillinases and cephalosporinases, of Gram-negative and Gram-positive bacteria. Cefuroxime has been shown to be active against most isolates of the following bacteria, both in vitro and in clinical infection: Enterobacter spp., Escherichia coli, Klebsiella spp., Haemophilus influenzae, Neisseria meningitidis, Neisseria gonorrhoeae, Staphylococcus aureus, Streptococcus pneumoniae, Streptococcus pyogenes. Cefuroxime is indicated for the treatment of patients with septicemia, meningitis, gonorrhea, lower respiratory tract, urinary tract, skin and skin-structure, bone and joint infections caused by susceptible strains of the designated organisms. — NCATS
Clinical trial activity
67 trials · 87 clinical orgs · 25 marketing orgs
Earliest trial started Apr 1, 1994 (NCT00530400)
Timeline
1980s
- Oct 19, 1983
Teligent Pharmaceuticals — Earliest FDA Approval
- Oct 19, 1983
Pharmaceutical Associates — Marketing Organization
- Oct 19, 1983
Teligent Pharmaceuticals — NDA Secondary Org
- Oct 19, 1983
Teligent Pharmaceuticals — NDA Organization
- Oct 19, 1983
Pharmaceutical Associates — NDA Secondary Org
- Jan 10, 1986
ACS Dobfar — Marketing Organization
- Jan 10, 1986
Eli Lilly — Marketing Organization
- Dec 28, 1987
GlaxoSmithKline — NDA Secondary Org
1990s
- Feb 26, 1993
Watson Pharmaceuticals — Marketing Organization
- Apr 16, 1998
Teva — Marketing Organization
- Sep 28, 1998
Fresenius — Marketing Organization
- Jan 1, 1999
Earliest Phase 2 Sponsor(trial)
2000s
- Feb 21, 2001
B. Braun — NDA Secondary Org
- Feb 15, 2002
Ranbaxy — Marketing Organization
- Oct 2, 2002
Apotex — Marketing Organization
- Jan 1, 2003
- Jan 1, 2003
Earliest Phase 3 Sponsor(trial)
- Apr 25, 2003
Sun Pharmaceuticals — Marketing Organization
- Jul 25, 2003
Lupin — Marketing Organization
- Oct 28, 2003
Fosun — Marketing Organization
- Jan 9, 2004
Hikma — Marketing Organization
- Oct 18, 2004
Ani Pharmaceuticals — Marketing Organization
- Jul 29, 2005
Atlantide Pharmaceuticals — Marketing Organization
- Jul 29, 2005
Wockhardt — Marketing Organization
- Jul 29, 2005
Chartwell Pharmaceuticals — Marketing Organization
- Mar 29, 2006
Aurobindo Pharma — Marketing Organization
- Feb 15, 2008
Orchid Pharma — Marketing Organization
- Feb 15, 2008
ANDA Repository — Marketing Organization
- Oct 15, 2008
Hospira — Marketing Organization
- Dec 30, 2009
Samson Medical — Marketing Organization
2010s
- Jun 7, 2010
Alkem Labs Ltd — Marketing Organization
Indications
Approved for
Studied for
- Antibiotic Prophylaxis · Phase 2
- Appendicitis · Phase 4
- Bacteremia · Phase 4
- Bacterial Infections · Phase 4
- Cesarean Section · Phase 4
- Colorectal Surgery · Phase 2
- Community-Acquired Infections · Phase 4
- Duodenal Ulcer · Phase 3
- Enterobacteriaceae Infections · Phase 3
- Erythema · Phase 4
- General Surgery · Phase 4
- Healthy Volunteers · Phase 1
- Helicobacter pylori · Phase 4
- HIV Infections · Phase 2
- Infant, Premature · Phase 4
- Intestinal Diseases · Phase 3
- Medicine, Chinese Traditional · Early Phase 1
- Obesity · Phase 4
- Osteoarthritis · Phase 4
- Osteoarthritis, Knee · Phase 4
- Pancreatic Neoplasms · Phase 4
- Pneumonia · Phase 3
- Postoperative Complications · Phase 4
- Respiratory Tract Infections · Early Phase 1
- Signs and Symptoms · Phase 4
- Sinusitis · Phase 2
- Spondylolisthesis · Phase 4
- Streptococcal Infections · Phase 4
- Surgical Wound Infection · Phase 4
- Urinary Bladder Neoplasms · Phase 3
- Urinary Tract Infections · Phase 4
- Wound Infection · Phase 4
- Wounds and Injuries · 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
- approvedOct 19, 1983
Chemistry & pharmacology
SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1- Mol. weight
- 424.39 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
Sources
- ChEMBLCHEMBL1436 ↗
- WikipediaCefuroxime ↗
- NCATSO1R9FJ93ED ↗
- ChEMBLCHEMBL2146124 ↗
- ChEMBLCHEMBL1697786 ↗
- ChEMBLCHEMBL1095930 ↗
Also known as
- 640/359
- (6r,7r)-3-[(carbamoyloxy)methyl]-7-{[(2z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-3-[(carbamoyloxy)methyl]-7-{[(2z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- acetoxyethylcefuroxime
- altacef
- biofuroxim
- britacef
- cci 15641
- cci-15641
- cci-15641
- cci-15641
- cefaloxime
- cefasyn
- cefazine
- ceftin
- ceftin
- ceftin
- ceftin
- cefuoxim
- cefurax
- cefuroxim
- cefuroxim
- cefuroxim
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime
- cefuroxime 1-acetoxyethyl ester
- cefuroxime acid
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime axetil
- cefuroxime pivoxetil
- cefuroxime pivoxetil
- cefuroxime pivoxetil
- cefuroxime pivoxetil
- cefuroxime pivoxetil
- cefuroxime sodium
- cefuroxime sodium
- cefuroxime sodium
- cefuroxime sodium
- cefuroxime sodium salt
- cefuroximine
- cefuroximine
- cefuroximo
- cefuroximo
- cefuroximum
- cefuroximum
- cephuroxime
- cephuroxime
- cephuroxime
- kefurox
- kefurox
- oraxim
- zinacef
- zinacef
- zinacef
- zinacef danmark
- zinacef danmark
- zinnat
- zinnat
- zinnat
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06351891 | Phase 4 | Apr 30, 2024 | Shandong University |
| NCT06255366 | Phase 4 | Mar 28, 2024 | Chengdu University of Traditional Chinese Medicines |
| NCT05750966 | N/A | Jul 19, 2023 | University of Amsterdam, ZonMw: The Netherlands Organisation for Health Research and Development |
| NCT05784311 | Phase 4 | Mar 6, 2023 | Leiden University |
| NCT05609240 | Phase 2 | Jan 1, 2023 | Aneurin Bevan University Health Board, University of Birmingham, University of Leeds |
| NCT05337566 | N/A | Sep 5, 2022 | Kuopio University Hospital, University of Helsinki, University of Oulu, University of Tampere, University of Turku |
| NCT05392634 | Phase 3 | Feb 2, 2022 | Government of Russia, The Foundation for Cancer Research Support (RakFond) |
| NCT05398081 | Phase 2 | Dec 1, 2021 | University of Ibadan |
| NCT04723472 | N/A | Oct 1, 2021 | Huazhong University of Science and Technology, ShanghaiDongfang Hospital |
| NCT04479657 | Early Phase 1 (Phase 1) | Aug 31, 2020 | China Academy of Chinese Medical Sciences, Tsinghua University |
| NCT04378868 | Phase 4 | May 18, 2020 | University of Helsinki |
| NCT04161599 | Phase 4 | Feb 29, 2020 | Universidad Autonoma de Barcelona |
| NCT04212078 | Phase 1/Phase 2 (Phase 2) | Jul 29, 2019 | National University of Malaysia, Santen Inc., UKM Medical Centre |
| NCT04009772 | Phase 2/Phase 3 (Phase 3) | Jul 1, 2019 | Assiut University |
| NCT05577273 | N/A | Aug 14, 2018 | Technion University |
| NCT03716804 | Phase 4 | Jun 6, 2018 | Bangladesh Medical University |
| NCT04303390 | Phase 4 | Feb 6, 2018 | Saud Al Babtain Cardiac Center |
| NCT03221504 | N/A | Jan 1, 2018 | Medical University of Warsaw |
| NCT03108690 | Phase 4 | May 1, 2017 | University of Copenhagen |
| NCT03141476 | Phase 4 | Mar 1, 2017 | University of Hamburg |
Organizations
Research & Development (87)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| University of Copenhagen | Academic/Hospital | 5 | 2 | 2 | 2001 |
| MDS Pharma | For profit | 4 | 0 | 1 | 2004 |
| Sandoz | For profit | 4 | 4 | 1 | 2004 |
| Teva | For profit | 4 | 4 | 1 | 2003 |
| University of Ljubljana | Academic/Hospital | 3 | 3 | 2 | 2006 |
| Benazir Bhutto Hospital, Rawalpindi | Academic/Hospital | 2 | 2 | 1 | 2013 |
| Gateway Medical Research | For profit | 2 | 0 | 1 | 2003 |
| PRACS | For profit | 2 | 0 | 1 | 2004 |
| Santen Inc. | For profit | 2 | 0 | 2 | 2003 |
| Universidad Autonoma de Barcelona | Academic/Hospital | 2 | 2 | 1 | 2015 |
| University of Geneva | Academic/Hospital | 2 | 0 | 1 | 1994 |
| University of Helsinki | Academic/Hospital | 2 | 2 | 2 | 2020 |
| University of Leeds | Academic/Hospital | 2 | 2 | 1 | 2015 |
| University of Southern Denmark | Academic/Hospital | 2 | 2 | 1 | 2014 |
| Aarhus University | Academic/Hospital | 1 | 1 | 1 | 2001 |
| Aase and Ejnar Danielsens Foundation | Academic/Hospital | 1 | 0 | 1 | 2014 |
| Adams Laboratories | For profit | 1 | 0 | 1 | 1999 |
| Aneurin Bevan University Health Board | Academic/Hospital | 1 | 0 | 1 | 2023 |
| Assiut University | Academic/Hospital | 1 | 1 | 1 | 2019 |
| Bangladesh Medical University | Academic/Hospital | 1 | 1 | 1 | 2018 |
Marketing (31)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| ACS Dobfar | For profit | MKTG | Jan 10, 1986 |
| ACS Dobfar | For profit | SYN | May 30, 1997 |
| ANDA Repository | For profit | MKTG | Feb 15, 2008 |
| Alkem Labs Ltd | For profit | MKTG | Jun 7, 2010 |
| Ani Pharmaceuticals | For profit | MKTG | Oct 18, 2004 |
| Ani Pharmaceuticals | For profit | SYN | Oct 18, 2004 |
| Apotex | For profit | MKTG | Oct 2, 2002 |
| Atlantide Pharmaceuticals | For profit | MKTG | Jul 29, 2005 |
| Aurobindo Pharma | For profit | MKTG | Mar 29, 2006 |
| Aurobindo Pharma | For profit | SYN | Mar 29, 2006 |
| B. Braun | For profit | NDA2 | Feb 21, 2001 |
| Chartwell Pharmaceuticals | For profit | MKTG | Jul 29, 2005 |
| Eli Lilly | For profit | MKTG | Jan 10, 1986 |
| Fosun | For profit | MKTG | Oct 28, 2003 |
| Fresenius | For profit | MKTG | Sep 28, 1998 |
| GlaxoSmithKline | For profit | NDA2 | Dec 28, 1987 |
| Hikma | For profit | MKTG | Jan 9, 2004 |
| Hikma | For profit | SYN | Jan 9, 2004 |
| Hospira | For profit | MKTG | Oct 15, 2008 |
| Lupin | For profit | MKTG | Jul 25, 2003 |
| Orchid Pharma | For profit | MKTG | Feb 15, 2008 |
| Pharmaceutical Associates | For profit | MKTG | Oct 19, 1983 |
| Pharmaceutical Associates | For profit | NDA2 | Oct 19, 1983 |
| Ranbaxy | For profit | MKTG | Feb 15, 2002 |
| Samson Medical | For profit | MKTG | Dec 30, 2009 |
| Sun Pharmaceuticals | For profit | MKTG | Apr 25, 2003 |
| Teligent Pharmaceuticals | For profit | NDA2 | Oct 19, 1983 |
| Teligent Pharmaceuticals | For profit | NDA | Oct 19, 1983 |
| Teva | For profit | MKTG | Apr 16, 1998 |
| Watson Pharmaceuticals | For profit | MKTG | Feb 26, 1993 |
| Wockhardt | For profit | MKTG | Jul 29, 2005 |