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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
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
Selecting new drugs for pain control: evidence-based decisions or clinical impressions?
2002 Aug
Efficacy and safety of intravenous parecoxib sodium in relieving acute postoperative pain following gynecologic laparotomy surgery.
2002 Aug
Valdecoxib, a cyclooxygenase-2-specific inhibitor, is effective in treating primary dysmenorrhea.
2002 Aug
Gateways to clinical trials.
2002 Dec
Valdecoxib (Pharmacia).
2002 Feb
Effects of parecoxib, a parenteral COX-2-specific inhibitor, on the pharmacokinetics and pharmacodynamics of propofol.
2002 Jan
Randomized placebo-controlled trial comparing efficacy and safety of valdecoxib with naproxen in patients with osteoarthritis.
2002 Jun
Nonsteroidal anti-inflammatory drugs, coxibs, and cardio-renal physiology: a mechanism-based approach.
2002 Mar 21
Valdecoxib is more efficacious than rofecoxib in relieving pain associated with oral surgery.
2002 Mar-Apr
The analgesic efficacy of valdecoxib vs. oxycodone/acetaminophen after oral surgery.
2002 May
Evaluation of efficacy, safety and tolerability of valdecoxib in osteo-arthritis patients--an Indian study.
2002 Nov
The influence of parecoxib, a parenteral cyclooxygenase-2 specific inhibitor, on the pharmacokinetics and clinical effects of midazolam.
2002 Sep
Disposition of a specific cyclooxygenase-2 inhibitor, valdecoxib, in human.
2002 Sep
[Pharmacology of cyclooxygenase 2 inhibition].
2003
[Coxibs: highly selective cyclooxygenase-2 inhibitors. Part II. Side effects].
2003 Apr
The role of cyclooxygenase selective inhibitors in the gastrointestinal tract.
2003 Dec
The COX-2 specific inhibitor, valdecoxib, is an effective, opioid-sparing analgesic in patients undergoing total knee arthroplasty.
2003 Feb
Review article: The pharmacological properties and clinical use of valdecoxib, a new cyclo-oxygenase-2-selective inhibitor.
2003 Feb 15
Gateways to clinical trials.
2003 Jan-Feb
Efficacy and safety of the first parenteral selective COX-2 inhibitor, parecoxib sodium, in adult patients with postoperative pain.
2003 Jul
Differential inhibition of fracture healing by non-selective and cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs.
2003 Jul
[Tolerable pain therapy in rheumatism saves long-term costs. Despite this most COX-2 candidates receive conventional NSAID therapy].
2003 Jul 24
Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population.
2003 Jul-Aug
Gateways to clinical trials. March 2003.
2003 Mar
Gateways to clinical trials.
2003 May
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
Single doses of parecoxib sodium intravenously are as effective as ketorolac in reducing pain after oral surgery.
2003 Sep
Development and validation of an automated SPE-LC-MS/MS assay for valdecoxib and its hydroxylated metabolite in human plasma.
2003 Sep 15
Clinical pharmacology of novel selective COX-2 inhibitors.
2004
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor.
2004 Feb
S-adenosyl methionine (SAMe) versus celecoxib for the treatment of osteoarthritis symptoms: a double-blind cross-over trial. [ISRCTN36233495].
2004 Feb 26
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.
2004 Jan
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
Valdecoxib versus rofecoxib in acute postsurgical pain: results of a randomized controlled trial.
2004 May
Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic.
2004 May
Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters.
2004 May
A systematic review of COX-2 inhibitors compared with traditional NSAIDs, or different COX-2 inhibitors for post-operative pain.
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
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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