Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H14N2O3S |
Molecular Weight | 314.3607 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1c(-c2ccc(cc2)S(=O)(=O)N)c(-c3ccccc3)no1
InChI
InChIKey=LNPDTQAFDNKSHK-UHFFFAOYSA-N
InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
Molecular Formula | C16H14N2O3S |
Molecular Weight | 314.3607 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15494548 |
0.005 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | BEXTRA Approved UseBEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea. Launch Date1.00586881E12 |
|||
Palliative | BEXTRA Approved UseBEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea. Launch Date1.00586881E12 |
|||
Primary | BEXTRA Approved UseBEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea. Launch Date1.00586881E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
161.1 ng/mL |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
12 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
14 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
26 ng/mL |
5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
24 ng/mL |
10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
26 ng/mL |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1385 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16599270/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.8 ng/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1 ng/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2 ng/mL |
5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2 ng/mL |
10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2 ng/mL |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1479 ng × h/mL |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
167 ng × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
175 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
198 ng × h/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
332 ng × h/mL |
5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
341 ng × h/mL |
10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
371 ng × h/mL |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9062 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16599270/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
15 ng × h/mL |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
18 ng × h/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
19 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
31 ng × h/mL |
5 mg 2 times / day steady-state, oral dose: 5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
33 ng × h/mL |
10 mg 2 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
36 ng × h/mL |
20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
1-HYDROXYVALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.11 h |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16599270/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
VALDECOXIB serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
VALDECOXIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.28 |
unhealthy, 18-92 n = 420 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 18-92 Sex: M+F Population Size: 420 Sources: Page: p.28 |
Other AEs: Gastrointestinal ulcer haemorrhage... Other AEs: Gastrointestinal ulcer haemorrhage (significant, 0.48%) Sources: Page: p.28 |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 32.3 ±10.9 n = 101 Health Status: unhealthy Condition: Acute ankle sprain Age Group: 32.3 ±10.9 Sex: M+F Population Size: 101 Sources: Page: p.462 |
Disc. AE: Allergic rash, Dizziness... Other AEs: Dyspepsia, Gastritis... AEs leading to discontinuation/dose reduction: Allergic rash (grade 2, 1%) Other AEs:Dizziness (grade 2, 1%) Dyspepsia (2%) Sources: Page: p.462Gastritis (5.9%) |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Disc. AE: Hypertension, Peripheral edema... AEs leading to discontinuation/dose reduction: Hypertension (1.7%) Sources: Page: p.71Peripheral edema (1.7%) Abdominal pain (2.7%) Duodenal ulcer (0.2%) Dyspepsia (2.2%) Gastric ulcer (1.5%) Nausea (0.5%) Vomiting (0.2%) Rash (1%) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.3 |
Disc. AE: Gastrointestinal perforation, Gastrointestinal ulcer... Other AEs: Exfoliative dermatitis... AEs leading to discontinuation/dose reduction: Gastrointestinal perforation (grade 3-5) Other AEs:Gastrointestinal ulcer (grade 3-5) Gastrointestinal bleeding (grade 3-5) Exfoliative dermatitis Sources: Page: p.3 |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.1 |
Disc. AE: Toxic epidermal necrolysis, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Toxic epidermal necrolysis (grade 3-5) Sources: Page: p.1Stevens-Johnson syndrome (grade 3-5) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.1, 9 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.1, 9 |
Other AEs: Erythema multiforme... Other AEs: Erythema multiforme (grade 3-5) Sources: Page: p.1, 9 |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.9 |
Other AEs: Anaphylactic reaction, Angioedema... Other AEs: Anaphylactic reaction Sources: Page: p.9Angioedema |
20 mg 1 times / day multiple, oral (max) Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.70 |
unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: Page: p.70 |
Disc. AE: Peripheral edema, Halitosis... AEs leading to discontinuation/dose reduction: Peripheral edema (2.2%) Sources: Page: p.70Halitosis (0.3%) Abdominal pain (5.5%) Dyspepsia (6.2%) Gastroenteritis (1.2%) |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.69 |
unhealthy n = 430 Health Status: unhealthy Condition: Arthritis Sex: M+F Population Size: 430 Sources: Page: p.69 |
Disc. AE: Abdominal pain, Diarrhea... AEs leading to discontinuation/dose reduction: Abdominal pain (1.6%) Sources: Page: p.69Diarrhea (0.7%) Dyspepsia (1.4%) Nausea (0.9%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal ulcer haemorrhage | significant, 0.48% | 80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.28 |
unhealthy, 18-92 n = 420 Health Status: unhealthy Condition: Rheumatoid arthritis Age Group: 18-92 Sex: M+F Population Size: 420 Sources: Page: p.28 |
Dyspepsia | 2% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 32.3 ±10.9 n = 101 Health Status: unhealthy Condition: Acute ankle sprain Age Group: 32.3 ±10.9 Sex: M+F Population Size: 101 Sources: Page: p.462 |
Gastritis | 5.9% | 40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 32.3 ±10.9 n = 101 Health Status: unhealthy Condition: Acute ankle sprain Age Group: 32.3 ±10.9 Sex: M+F Population Size: 101 Sources: Page: p.462 |
Allergic rash | grade 2, 1% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 32.3 ±10.9 n = 101 Health Status: unhealthy Condition: Acute ankle sprain Age Group: 32.3 ±10.9 Sex: M+F Population Size: 101 Sources: Page: p.462 |
Dizziness | grade 2, 1% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.462 |
unhealthy, 32.3 ±10.9 n = 101 Health Status: unhealthy Condition: Acute ankle sprain Age Group: 32.3 ±10.9 Sex: M+F Population Size: 101 Sources: Page: p.462 |
Duodenal ulcer | 0.2% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Vomiting | 0.2% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Nausea | 0.5% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Rash | 1% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Gastric ulcer | 1.5% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Hypertension | 1.7% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Peripheral edema | 1.7% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Dyspepsia | 2.2% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Abdominal pain | 2.7% Disc. AE |
40 mg 2 times / day multiple, oral Highest studied dose Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: Page: p.71 |
unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: Page: p.71 |
Exfoliative dermatitis | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.3 |
|
Gastrointestinal bleeding | grade 3-5 Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.3 |
Gastrointestinal perforation | grade 3-5 Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.3 |
Gastrointestinal ulcer | grade 3-5 Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.3 |
Stevens-Johnson syndrome | grade 3-5 Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.1 |
Toxic epidermal necrolysis | grade 3-5 Disc. AE |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.1 |
Erythema multiforme | grade 3-5 | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.1, 9 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.1, 9 |
Anaphylactic reaction | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.9 |
|
Angioedema | 10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.9 |
unhealthy Health Status: unhealthy Condition: Osteoarthritis | Adult rheumatoid arthritis Sources: Page: p.9 |
|
Halitosis | 0.3% Disc. AE |
20 mg 1 times / day multiple, oral (max) Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.70 |
unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: Page: p.70 |
Gastroenteritis | 1.2% Disc. AE |
20 mg 1 times / day multiple, oral (max) Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.70 |
unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: Page: p.70 |
Peripheral edema | 2.2% Disc. AE |
20 mg 1 times / day multiple, oral (max) Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.70 |
unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: Page: p.70 |
Abdominal pain | 5.5% Disc. AE |
20 mg 1 times / day multiple, oral (max) Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.70 |
unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: Page: p.70 |
Dyspepsia | 6.2% Disc. AE |
20 mg 1 times / day multiple, oral (max) Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.70 |
unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: Page: p.70 |
Diarrhea | 0.7% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.69 |
unhealthy n = 430 Health Status: unhealthy Condition: Arthritis Sex: M+F Population Size: 430 Sources: Page: p.69 |
Nausea | 0.9% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.69 |
unhealthy n = 430 Health Status: unhealthy Condition: Arthritis Sex: M+F Population Size: 430 Sources: Page: p.69 |
Dyspepsia | 1.4% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.69 |
unhealthy n = 430 Health Status: unhealthy Condition: Arthritis Sex: M+F Population Size: 430 Sources: Page: p.69 |
Abdominal pain | 1.6% Disc. AE |
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Page: p.69 |
unhealthy n = 430 Health Status: unhealthy Condition: Arthritis Sex: M+F Population Size: 430 Sources: Page: p.69 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Mechanism of inhibition of novel COX-2 inhibitors. | 2002 |
|
The biochemical selectivity of novel COX-2 inhibitors in whole blood assays of COX-isozyme activity. | 2002 |
|
Valdecoxib. | 2002 |
|
Gateways to clinical trials. | 2002 Dec |
|
Right ballpark, wrong base: assessing safety of NSAIDs. | 2002 Jun |
|
Evaluation of efficacy, safety and tolerability of valdecoxib in osteo-arthritis patients--an Indian study. | 2002 Nov |
|
Gateways to Clinical Trials. | 2002 Sep |
|
The influence of parecoxib, a parenteral cyclooxygenase-2 specific inhibitor, on the pharmacokinetics and clinical effects of midazolam. | 2002 Sep |
|
[Adverse effects of NSAID are insidious. No pain--despite life threatening gastric hemorrhage]. | 2002 Sep 12 |
|
COX-2: where are we in 2003?--distinction from NSAIDs becoming blurred. | 2003 |
|
COX-2: Where are we in 2003? - Be strong and resolute: continue to use COX-2 selective inhibitors at recommended dosages in appropriate patients. | 2003 |
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[Pharmacology of cyclooxygenase 2 inhibition]. | 2003 |
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[Coxibs: highly selective cyclooxygenase-2 inhibitors. Part II. Side effects]. | 2003 Apr |
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Valdecoxib-induced toxic epidermal necrolysis in a patient allergic to sulfa drugs. | 2003 Apr |
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Simultaneous assessment of drug interactions with low- and high-extraction opioids: application to parecoxib effects on the pharmacokinetics and pharmacodynamics of fentanyl and alfentanil. | 2003 Apr |
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Characterization of celecoxib and valdecoxib binding to cyclooxygenase. | 2003 Apr |
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Pharmacokinetics and metabolism of a COX-2 inhibitor, valdecoxib, in mice. | 2003 Apr |
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The COX-2 specific inhibitor, valdecoxib, is an effective, opioid-sparing analgesic in patients undergoing total knee arthroplasty. | 2003 Feb |
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Clinical pharmacology of etoricoxib: a novel selective COX2 inhibitor. | 2003 Feb |
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Review article: The pharmacological properties and clinical use of valdecoxib, a new cyclo-oxygenase-2-selective inhibitor. | 2003 Feb 15 |
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Determination of valdecoxib and its metabolites in human urine by automated solid-phase extraction-liquid chromatography-tandem mass spectrometry. | 2003 Feb 25 |
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Gateways to clinical trials. | 2003 Jan-Feb |
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Cyclooxygenase-2: from arthritis treatment to new indications for the prevention and treatment of cancer. | 2003 Jan-Feb |
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New warnings for Bextra. | 2003 Jan-Feb |
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Differential inhibition of fracture healing by non-selective and cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs. | 2003 Jul |
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A comparison of the upper gastrointestinal mucosal effects of valdecoxib, naproxen and placebo in healthy elderly subjects. | 2003 Jul 1 |
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Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population. | 2003 Jul-Aug |
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Gateways to clinical trials. | 2003 Jun |
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Efficacy and safety of the cyclooxygenase 2 inhibitors parecoxib and valdecoxib in patients undergoing coronary artery bypass surgery. | 2003 Jun |
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[Progress in therapy of rheumatism. New coxib works especially fast]. | 2003 Jun 5 |
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Valdecoxib: a review. | 2003 Mar |
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Gateways to clinical trials. March 2003. | 2003 Mar |
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Gateways to clinical trials. | 2003 May |
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The COX-2 selective inhibitor, valdecoxib, does not impair platelet function in the elderly: results of a randomized controlled trial. | 2003 May |
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[Adverse effect-free analgesia. New COX-2 inhibitor is even more selective]. | 2003 May 1 |
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Clinical pharmacology of selective COX-2 inhibitors. | 2003 May-Aug |
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The burden of acute postoperative pain and the potential role of the COX-2-specific inhibitors. | 2003 Nov |
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Measuring dyspepsia-related health in randomized trials: the Severity of Dyspepsia Assessment (SODA) and its use in treatment with NSAIDs and COX-2-specific inhibitors. | 2003 Nov |
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Valdecoxib is as effective as diclofenac in the management of rheumatoid arthritis with a lower incidence of gastroduodenal ulcers: results of a 26-week trial. | 2003 Oct |
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[Pain therapy in rheumatism. After 65 years of age coxibs are the best choice]. | 2003 Oct 16 |
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Gateways to clinical trials. | 2003 Sep |
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Valdecoxib, a COX-2-specific inhibitor, does not affect cardiac repolarization. | 2003 Sep |
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Clinical pharmacology of novel selective COX-2 inhibitors. | 2004 |
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Quantitation of Valdecoxib in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection using liquid-liquid extraction. | 2004 Apr 5 |
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Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials. | 2004 Jan |
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Differential effects of selective COX-2 inhibitors on cell cycle regulation and proliferation of glioblastoma cell lines. | 2004 Jan |
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Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride. | 2004 Jan 19 |
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Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition. | 2004 Jan 29 |
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Collision-induced dissociation of valdecoxib metabolites: a novel rearrangement involving an isoxazole ring. | 2004 Mar |
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Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters. | 2004 May |
Sample Use Guides
Osteoarthritis and Adult Rheumatoid Arthritis: the recommended dose of BEXTRA Tablets (VALDECOXIB) for the relief of the signs and symptoms of arthritis is 10 mg once daily.
Primary Dysmenorrhea: the recommended dose of BEXTRA Tablets for treatment of primary dysmenorrhea is 20 mg twice daily, as needed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15494548
Valdecoxib potently inhibits recombinant COX-2, with an IC50 of 0.005 uM. Unique binding interactions of valdecoxib with COX-2 translate into a fast rate of inactivation of COX-2 (110,000 M/s). The overall saturation binding affinity for COX-2 of valdecoxib is 2.6 nM. Valdecoxib inhibits COX-1 in a competitive fashion only at very high concentrations IC50= 150 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:50:32 UTC 2021
by
admin
on
Fri Jun 25 21:50:32 UTC 2021
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Record UNII |
2919279Q3W
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Record Status |
Validated (UNII)
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Record Version |
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EMA ASSESSMENT REPORTS |
VALDYN (WITHDRAWN: ARTHRITIS, RHEUMATOID)
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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WHO-ATC |
M01AH03
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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EMA ASSESSMENT REPORTS |
BEXTRA (WITHDRAWN: DYSMENORRHEA)
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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EMA ASSESSMENT REPORTS |
VALDYN (WITHDRAWN: DYSMENORRHEA)
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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EMA ASSESSMENT REPORTS |
BEXTRA (WITHDRAWN: OSTEOARTHRITIS)
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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NCI_THESAURUS |
C1323
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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EMA ASSESSMENT REPORTS |
VALDYN (WITHDRAWN: OSTEOARTHRITIS)
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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EMA ASSESSMENT REPORTS |
BEXTRA (WITHDRAWN: ARTHRITIS, RHEUMATOID)
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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WHO-VATC |
QM01AH03
Created by
admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
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DB00580
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7302
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M11356
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PRIMARY | Merck Index | ||
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2799
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7815
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C1869
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SUB05065MIG
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Valdecoxib
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VALDECOXIB
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181695-72-7
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CHEMBL865
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119607
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278567
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2919279Q3W
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C406224
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2894
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Related Record | Type | Details | ||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL; URINE
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BINDER->LIGAND |
Plasma protein binding for valdecoxib is about 98% over the concentration range (21-2384 ng/mL).
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE | |||
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INHIBITOR -> TARGET |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
MAJOR
URINE
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE ACTIVE -> PARENT |
Plasma concentrations of valdecoxib were 10-20 fold higher than the corresponding SC-66905 (M1) concentrations. The metabolite M1 is a less potent COX-2 specific inhibitor than the parent.
MAJOR
PLASMA
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE ACTIVE -> PARENT |
FECAL
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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