valdecoxib
Trade name: Bextra
Approved
Nov 16, 2001
Valdecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Valdecoxib was manufactured and marketed under the brand name Bextra. Bextra was indicated for relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea. But in 2005 FDA requested that Pfizer withdraw Bextra from the American market, because the Agency had concluded that the overall risk versus benefit profile of Bextra was unfavorable. That conclusion was based on the potential increased risk for serious cardiovascular (CV) adverse events, an increased risk of serious skin reactions (e.g., toxic epidermal necrolysis, Stevens-Johnson syndrome, erythema multiforme) compared to other NSAIDs, and the fact that Bextra had not been shown to offer any unique advantages over the other available NSAIDs. — NCATS
Clinical trial activity
27 trials · 14 clinical orgs · 2 marketing orgs
Earliest trial started Jan 1, 2001 (NCT00021996)
Timeline
2000s
- Nov 16, 2001
G D Searle — Earliest FDA Approval
- Nov 16, 2001
G D Searle — NDA Organization
- Nov 16, 2001
G D Searle — NDA Secondary Org
- Nov 16, 2001
Pharmacia — NDA Secondary Org
- Jan 1, 2002
Earliest Phase 3 Sponsor(trial)
- Jan 1, 2003
Earliest Phase 2 Sponsor(trial)
Indications
Studied for
- Acute Pain · Phase 4
- Anterior Cruciate Ligament Injuries · Phase 4
- Arthritis, Rheumatoid · Phase 4
- Cholangiopancreatography, Endoscopic Retrograde · Phase 2/Phase 3
- Cholecystectomy, Laparoscopic · Phase 3
- Dysmenorrhea · Phase 4
- Hallux Valgus · Phase 3
- Hyperalgesia · Phase 4
- Knee · Phase 3
- Low Back Pain · Phase 4
- Neurosurgery · Phase 4
- Osteoarthritis · Phase 3
- Osteoarthritis, Knee · Phase 2
- Pain · Phase 4
- Pancreatitis · Phase 2/Phase 3
- Pharyngitis · Phase 3
- Postoperative Pain · Phase 4
- Sprains and Strains · Phase 4
Mechanism of action
- Cyclooxygenase-2INHIBITOR
PTGS2 inhibitor
Approval history
- approvedNov 16, 2001
Chemistry & pharmacology
SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C3=CC=C(C=C3)S(N)(=O)=O- Mol. weight
- 314.359 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaValdecoxib ↗
- NCATS2919279Q3W ↗
- ChEMBLCHEMBL865 ↗
Also known as
- 4-(5-methyl-3-phenyl-isoxazol-4-yl)benzenesulfonamide
- bextra
- bextra
- bextra
- bextra
- pfizer brand of valdecoxib
- sc 65872
- sc-65872
- sc-65872
- sc-65872
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valdecoxib
- valecoxib
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT00115752 | Phase 2 | Jun 20, 2005 | National Institute of Nursing Research (NINR) |
| NCT00260325 | Phase 4 | Aug 1, 2004 | National Institutes of Health (NIH), Pennsylvania State University, Pfizer |
| NCT00660855 | Phase 4 | Jun 1, 2004 | Pfizer |
| NCT00652808 | Phase 3 | May 1, 2004 | Pfizer |
| NCT00650598 | Phase 4 | Mar 1, 2004 | Pfizer |
| NCT01541137 | N/A | Mar 1, 2004 | Government of Finland, University of Helsinki |
| NCT00650039 | Phase 3 | Mar 1, 2004 | Pfizer |
| NCT00763997 | N/A | Feb 1, 2004 | Pfizer, Ruhr University Bochum |
| NCT01361789 | Phase 4 | Jan 1, 2004 | Baerum Hospital, University of Oslo |
| NCT00419549 | Phase 2/Phase 3 (Phase 3) | Oct 1, 2003 | All India Institute of Medical Sciences |
| NCT00648258 | Phase 3 | Jul 1, 2003 | Pfizer |
| NCT00657449 | Phase 4 | Jun 1, 2003 | Pfizer |
| NCT00650624 | Phase 2 | Jun 1, 2003 | Pfizer |
| NCT00651300 | Phase 3 | Apr 1, 2003 | Pfizer |
| NCT00650455 | Phase 4 | Feb 1, 2003 | Pfizer |
| NCT00647829 | Phase 3 | Feb 1, 2003 | Pfizer |
| NCT00636064 | Phase 3 | Jan 1, 2003 | Pfizer |
| NCT00649415 | Phase 4 | Jan 1, 2003 | Pfizer |
| NCT00653354 | Phase 3 | Dec 1, 2002 | Pfizer |
| NCT00671320 | Phase 4 | Dec 1, 2002 | Pfizer |
Organizations
Research & Development (14)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Pfizer | For profit | 20 | 17 | 4 | 2002 |
| Merck | For profit | 2 | 2 | 1 | 2002 |
| All India Institute of Medical Sciences | Academic/Hospital | 1 | 1 | 1 | 2003 |
| Baerum Hospital | Academic/Hospital | 1 | 0 | 1 | 2004 |
| Government of Finland | Government | 1 | 0 | 1 | 2004 |
| Harvard University | Academic/Hospital | 1 | 1 | 1 | 2001 |
| National Institute of Nursing Research (NINR) | Government | 1 | 1 | 1 | 2005 |
| National Institutes of Health (NIH) | Government | 1 | 0 | 1 | 2004 |
| Pennsylvania State University | Academic/Hospital | 1 | 1 | 1 | 2004 |
| Ruhr University Bochum | Academic/Hospital | 1 | 1 | 1 | 2004 |
| University of Helsinki | Academic/Hospital | 1 | 1 | 1 | 2004 |
| University of Oslo | Academic/Hospital | 1 | 1 | 1 | 2004 |
| University of Washington | Academic/Hospital | 1 | 1 | 1 | 2002 |
| Washington University in St. Louis | Academic/Hospital | 1 | 0 | 1 | 2002 |
Marketing (3)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| G D Searle | For profit | NDA | Nov 16, 2001 |
| G D Searle | For profit | NDA2 | Nov 16, 2001 |
| Pharmacia | For profit | NDA2 | Nov 16, 2001 |