cefprozil
Trade name: cefzil
Approved
Dec 23, 1991
Cefprozil is a 2nd generation cephalosporin that is FDA approved for the treatment of mild to moderate infections of upper respiratory tract, lower respiratory tract, and uncomplicated skin and skin-structure infections. Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Common adverse reactions include diarrhea, nausea, vomiting, dizziness, abdominal pain and vaginitis. Nephrotoxicity has been reported following concomitant administration of aminoglycoside antibiotics and cephalosporin antibiotics. Concomitant administration of probenecid doubled the AUC for cefprozil. — NCATS
Clinical trial activity
14 trials · 8 clinical orgs · 14 marketing orgs
Earliest trial started Sep 1, 2003 (NCT00840866)
Timeline
1990s
- Dec 23, 1991
Earliest FDA Approval
- Dec 23, 1991
Corden Pharma — NDA Secondary Org
- Dec 28, 1991
Bristol-Myers Squibb — First NDA Organization
- Dec 28, 1991
Bristol-Myers Squibb — NDA Organization
2000s
- Jan 1, 2003
- Nov 14, 2005
Chartwell Pharmaceuticals — Marketing Organization
- Nov 14, 2005
CASI Pharmaceuticals, Inc. — Marketing Organization
- Dec 6, 2005
Teva — Marketing Organization
- Dec 8, 2005
Lupin — Marketing Organization
- Dec 8, 2005
Sandoz — Marketing Organization
- Dec 8, 2005
Novartis — Marketing Organization
- Dec 19, 2005
Orchid Pharma — Marketing Organization
- Jun 30, 2006
Ranbaxy — Marketing Organization
- Jan 30, 2007
Aurobindo Pharma — Marketing Organization
- Jun 14, 2007
Wockhardt — Marketing Organization
- Mar 26, 2008
Apotex — Marketing Organization
2020s
- Apr 9, 2024
Alkem Labs Ltd — Marketing Organization
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 23, 1991
Chemistry & pharmacology
SMILES
CC=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- Mol. weight
- 389.43 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL3301800 ↗
- WikipediaCefprozil ↗
- NCATS1M698F4H4E ↗
- ChEMBLCHEMBL3184906 ↗
- ChEMBLCHEMBL276568 ↗
Also known as
- 7-(2-amino-2-(4-hydroxyphenyl)acetamido)-3-(propenyl)-3-cephem-4-carboxylic acid monohydrate
- arzimol
- bmy 28100
- bmy-28100
- bmy-28100-03-800
- bmy-28100-03-800
- brisoral
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil
- cefprozil anhydrous
- cefprozil anhydrous
- cefprozile
- cefprozil hydrate
- cefprozil monohydrate
- cefprozilo
- cefprozilo
- cefprozilum
- cefprozilum
- cefzil
- cefzil
- cefzil
- cefzil
- cephprozyl
- procef
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06494072 | Phase 4 | Aug 22, 2024 | Medical College of Wisconsin |
| NCT04414254 | Phase 1 | Sep 11, 2018 | Qingdao University |
| NCT00778739 | N/A | Jun 1, 2005 | Ranbaxy |
| NCT00778557 | N/A | Jun 1, 2005 | Ranbaxy |
| NCT00778245 | N/A | May 1, 2005 | Ranbaxy |
| NCT00778778 | N/A | May 1, 2005 | Ranbaxy |
| NCT00881400 | Phase 1 | Jun 1, 2004 | MDS Pharma, Sandoz |
| NCT00835354 | Phase 1 | May 1, 2004 | PRACS, Teva |
| NCT00881153 | Phase 1 | May 1, 2004 | MDS Pharma, Sandoz |
| NCT00835614 | Phase 1 | Apr 1, 2004 | PRACS, Teva |
| NCT00881426 | Phase 1 | Mar 1, 2004 | MDS Pharma, Sandoz |
| NCT00881855 | Phase 1 | Mar 1, 2004 | MDS Pharma, Sandoz |
| NCT00840281 | Phase 1 | Sep 1, 2003 | Gateway Medical Research, Teva |
| NCT00840866 | Phase 1 | Sep 1, 2003 | Gateway Medical Research, Teva |
Organizations
Research & Development (8)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| MDS Pharma | For profit | 4 | 0 | 1 | 2004 |
| Ranbaxy | For profit | 4 | 4 | 1 | 2005 |
| Sandoz | For profit | 4 | 4 | 1 | 2004 |
| Teva | For profit | 4 | 4 | 1 | 2003 |
| Gateway Medical Research | For profit | 2 | 0 | 1 | 2003 |
| PRACS | For profit | 2 | 0 | 1 | 2004 |
| Medical College of Wisconsin | Academic/Hospital | 1 | 1 | 1 | 2024 |
| Qingdao University | Academic/Hospital | 1 | 1 | 1 | 2018 |
Marketing (16)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Alkem Labs Ltd | For profit | MKTG | Apr 9, 2024 |
| Apotex | For profit | MKTG | Mar 26, 2008 |
| Aurobindo Pharma | For profit | MKTG | Jan 30, 2007 |
| Aurobindo Pharma | For profit | SYN | May 24, 2007 |
| Bristol-Myers Squibb | For profit | NDA | Dec 28, 1991 |
| CASI Pharmaceuticals, Inc. | For profit | MKTG | Nov 14, 2005 |
| Chartwell Pharmaceuticals | For profit | MKTG | Nov 14, 2005 |
| Corden Pharma | For profit | NDA2 | Dec 23, 1991 |
| Lupin | For profit | MKTG | Dec 8, 2005 |
| Novartis | For profit | MKTG | Dec 8, 2005 |
| Orchid Pharma | For profit | MKTG | Dec 19, 2005 |
| Ranbaxy | For profit | MKTG | Jun 30, 2006 |
| Sandoz | For profit | MKTG | Dec 8, 2005 |
| Teva | For profit | MKTG | Dec 6, 2005 |
| Teva | For profit | SYN | Dec 8, 2005 |
| Wockhardt | For profit | MKTG | Jun 14, 2007 |