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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
Structure of VALDECOXIB

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)

HIDE SMILES / InChI

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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.005 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BEXTRA

Approved Use

BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea.

Launch Date

1.00586881E12
Palliative
BEXTRA

Approved Use

BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea.

Launch Date

1.00586881E12
Primary
BEXTRA

Approved Use

BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis. For the treatment of primary dysmenorrhea.

Launch Date

1.00586881E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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%)
Dizziness (grade 2, 1%)
Other AEs:
Dyspepsia (2%)
Gastritis (5.9%)
Sources: Page: p.462
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%)
Peripheral 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%)
Sources: Page: p.71
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)
Gastrointestinal ulcer (grade 3-5)
Gastrointestinal bleeding (grade 3-5)
Other AEs:
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)
Stevens-Johnson syndrome (grade 3-5)
Sources: Page: p.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.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
Angioedema
Sources: Page: p.9
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%)
Halitosis (0.3%)
Abdominal pain (5.5%)
Dyspepsia (6.2%)
Gastroenteritis (1.2%)
Sources: Page: p.70
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%)
Diarrhea (0.7%)
Dyspepsia (1.4%)
Nausea (0.9%)
Sources: Page: p.69
AEs

AEs

AESignificanceDosePopulation
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

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
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
[Pharmacology of cyclooxygenase 2 inhibition].
2003
[Coxibs: highly selective cyclooxygenase-2 inhibitors. Part II. Side effects].
2003 Apr
Valdecoxib-induced toxic epidermal necrolysis in a patient allergic to sulfa drugs.
2003 Apr
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
Characterization of celecoxib and valdecoxib binding to cyclooxygenase.
2003 Apr
Pharmacokinetics and metabolism of a COX-2 inhibitor, valdecoxib, in mice.
2003 Apr
The COX-2 specific inhibitor, valdecoxib, is an effective, opioid-sparing analgesic in patients undergoing total knee arthroplasty.
2003 Feb
Clinical pharmacology of etoricoxib: a novel selective COX2 inhibitor.
2003 Feb
Review article: The pharmacological properties and clinical use of valdecoxib, a new cyclo-oxygenase-2-selective inhibitor.
2003 Feb 15
Determination of valdecoxib and its metabolites in human urine by automated solid-phase extraction-liquid chromatography-tandem mass spectrometry.
2003 Feb 25
Gateways to clinical trials.
2003 Jan-Feb
Cyclooxygenase-2: from arthritis treatment to new indications for the prevention and treatment of cancer.
2003 Jan-Feb
New warnings for Bextra.
2003 Jan-Feb
Differential inhibition of fracture healing by non-selective and cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs.
2003 Jul
A comparison of the upper gastrointestinal mucosal effects of valdecoxib, naproxen and placebo in healthy elderly subjects.
2003 Jul 1
Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population.
2003 Jul-Aug
Gateways to clinical trials.
2003 Jun
Efficacy and safety of the cyclooxygenase 2 inhibitors parecoxib and valdecoxib in patients undergoing coronary artery bypass surgery.
2003 Jun
[Progress in therapy of rheumatism. New coxib works especially fast].
2003 Jun 5
Valdecoxib: a review.
2003 Mar
Gateways to clinical trials. March 2003.
2003 Mar
Gateways to clinical trials.
2003 May
The COX-2 selective inhibitor, valdecoxib, does not impair platelet function in the elderly: results of a randomized controlled trial.
2003 May
[Adverse effect-free analgesia. New COX-2 inhibitor is even more selective].
2003 May 1
Clinical pharmacology of selective COX-2 inhibitors.
2003 May-Aug
The burden of acute postoperative pain and the potential role of the COX-2-specific inhibitors.
2003 Nov
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
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
[Pain therapy in rheumatism. After 65 years of age coxibs are the best choice].
2003 Oct 16
Gateways to clinical trials.
2003 Sep
Valdecoxib, a COX-2-specific inhibitor, does not affect cardiac repolarization.
2003 Sep
Clinical pharmacology of novel selective COX-2 inhibitors.
2004
Quantitation of Valdecoxib in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection using liquid-liquid extraction.
2004 Apr 5
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.
2004 Jan
Differential effects of selective COX-2 inhibitors on cell cycle regulation and proliferation of glioblastoma cell lines.
2004 Jan
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride.
2004 Jan 19
Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition.
2004 Jan 29
Collision-induced dissociation of valdecoxib metabolites: a novel rearrangement involving an isoxazole ring.
2004 Mar
Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters.
2004 May
Patents

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
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 Fri Jun 25 21:50:32 UTC 2021
Edited
by admin
on Fri Jun 25 21:50:32 UTC 2021
Record UNII
2919279Q3W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALDECOXIB
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
VALDECOXIB [WHO-DD]
Common Name English
SC-65872
Code English
VALDYN
Brand Name English
VALDECOXIB [MART.]
Common Name English
VALDECOXIB [VANDF]
Common Name English
VALDECOXIB [MI]
Common Name English
4-(5-METHYL-3-PHENYLISOXAZOL-4-YL)BENZENESULFONAMIDE
Systematic Name English
VALDECOXIB [USAN]
Common Name English
BEXTRA
Brand Name English
VALDECOXIB [HSDB]
Common Name English
VALDECOXIB [INN]
Common Name English
VALDECOXIB [EMA EPAR]
Common Name English
P-(5-METHYL-3-PHENYL-4-ISOXAZOLYL)BENZENESULFONAMIDE
Common Name English
VALDECOXIB [ORANGE BOOK]
Common Name English
NSC-759846
Code English
Classification Tree Code System Code
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
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
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
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
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
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
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
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
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
Code System Code Type Description
DRUG BANK
DB00580
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
HSDB
7302
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
MERCK INDEX
M11356
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2799
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
INN
7815
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
NCI_THESAURUS
C1869
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
EVMPD
SUB05065MIG
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
LACTMED
Valdecoxib
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
WIKIPEDIA
VALDECOXIB
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
CAS
181695-72-7
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
EPA CompTox
181695-72-7
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
ChEMBL
CHEMBL865
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
PUBCHEM
119607
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
RXCUI
278567
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY RxNorm
FDA UNII
2919279Q3W
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
MESH
C406224
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
IUPHAR
2894
Created by admin on Fri Jun 25 21:50:32 UTC 2021 , Edited by admin on Fri Jun 25 21:50:32 UTC 2021
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL; URINE
BINDER->LIGAND
Plasma protein binding for valdecoxib is about 98% over the concentration range (21-2384 ng/mL).
BINDING
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
INHIBITOR -> TARGET
Related Record Type Details
METABOLITE ACTIVE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
MAJOR
URINE
PRODRUG -> METABOLITE ACTIVE
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
METABOLITE -> PARENT
MINOR
URINE
METABOLITE ACTIVE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
ORAL BIOAVAILABILITY PHARMACOKINETIC ORAL ADMINISTRATION

Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC