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 |
---|---|---|
4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. | 2000 Mar 9 |
|
Parecoxib (parecoxib sodium). | 2001 |
|
A three-step kinetic mechanism for selective inhibition of cyclo-oxygenase-2 by diarylheterocyclic inhibitors. | 2001 Aug 1 |
|
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. | 2001 Feb |
|
A pharmacokinetic study of intramuscular (i.m.) parecoxib sodium in normal subjects. | 2001 Oct |
|
Upper gastrointestinal safety evaluation of parecoxib sodium, a new parenteral cyclooxygenase-2-specific inhibitor, compared with ketorolac, naproxen, and placebo. | 2001 Sep |
|
The injectable cyclooxygenase-2-specific inhibitor parecoxib sodium has analgesic efficacy when administered preoperatively. | 2001 Sep |
|
Etoricoxib. | 2002 |
|
Development and clinical application of COX-2-selective inhibitors for the treatment of osteoarthritis and rheumatoid arthritis. | 2002 |
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Selecting new drugs for pain control: evidence-based decisions or clinical impressions? | 2002 Aug |
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Efficacy and safety of intravenous parecoxib sodium in relieving acute postoperative pain following gynecologic laparotomy surgery. | 2002 Aug |
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Valdecoxib, a cyclooxygenase-2-specific inhibitor, is effective in treating primary dysmenorrhea. | 2002 Aug |
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Gateways to clinical trials. | 2002 Dec |
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Valdecoxib (Pharmacia). | 2002 Feb |
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Effects of parecoxib, a parenteral COX-2-specific inhibitor, on the pharmacokinetics and pharmacodynamics of propofol. | 2002 Jan |
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Randomized placebo-controlled trial comparing efficacy and safety of valdecoxib with naproxen in patients with osteoarthritis. | 2002 Jun |
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Nonsteroidal anti-inflammatory drugs, coxibs, and cardio-renal physiology: a mechanism-based approach. | 2002 Mar 21 |
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Valdecoxib is more efficacious than rofecoxib in relieving pain associated with oral surgery. | 2002 Mar-Apr |
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The analgesic efficacy of valdecoxib vs. oxycodone/acetaminophen after oral surgery. | 2002 May |
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Evaluation of efficacy, safety and tolerability of valdecoxib in osteo-arthritis patients--an Indian study. | 2002 Nov |
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The influence of parecoxib, a parenteral cyclooxygenase-2 specific inhibitor, on the pharmacokinetics and clinical effects of midazolam. | 2002 Sep |
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Disposition of a specific cyclooxygenase-2 inhibitor, valdecoxib, in human. | 2002 Sep |
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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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The role of cyclooxygenase selective inhibitors in the gastrointestinal tract. | 2003 Dec |
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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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Review article: The pharmacological properties and clinical use of valdecoxib, a new cyclo-oxygenase-2-selective inhibitor. | 2003 Feb 15 |
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Gateways to clinical trials. | 2003 Jan-Feb |
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Efficacy and safety of the first parenteral selective COX-2 inhibitor, parecoxib sodium, in adult patients with postoperative pain. | 2003 Jul |
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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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[Tolerable pain therapy in rheumatism saves long-term costs. Despite this most COX-2 candidates receive conventional NSAID therapy]. | 2003 Jul 24 |
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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. March 2003. | 2003 Mar |
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Gateways to clinical trials. | 2003 May |
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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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Single doses of parecoxib sodium intravenously are as effective as ketorolac in reducing pain after oral surgery. | 2003 Sep |
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Development and validation of an automated SPE-LC-MS/MS assay for valdecoxib and its hydroxylated metabolite in human plasma. | 2003 Sep 15 |
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Clinical pharmacology of novel selective COX-2 inhibitors. | 2004 |
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Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor. | 2004 Feb |
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S-adenosyl methionine (SAMe) versus celecoxib for the treatment of osteoarthritis symptoms: a double-blind cross-over trial. [ISRCTN36233495]. | 2004 Feb 26 |
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Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials. | 2004 Jan |
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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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Valdecoxib versus rofecoxib in acute postsurgical pain: results of a randomized controlled trial. | 2004 May |
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Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic. | 2004 May |
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Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters. | 2004 May |
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A systematic review of COX-2 inhibitors compared with traditional NSAIDs, or different COX-2 inhibitors for post-operative pain. | 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
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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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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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