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Details

Stereochemistry ACHIRAL
Molecular Formula C16H14N2O3S
Molecular Weight 314.359
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALDECOXIB

SMILES

CC1=C(C(=NO1)C2=CC=CC=C2)C3=CC=C(C=C3)S(N)(=O)=O

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 314.359
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Dynastat

Approved Use

Dynastat is used for the short-term treatment of pain in adults after an operation.

Launch Date

2002
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

2001
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

2001
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

2001
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
A pharmacokinetic study of intramuscular (i.m.) parecoxib sodium in normal subjects.
2001 Oct
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
Efficacy and safety of intravenous parecoxib sodium in relieving acute postoperative pain following gynecologic laparotomy surgery.
2002 Aug
Gateways to clinical trials.
2002 Dec
Upper GI mucosal effects of parecoxib sodium in healthy elderly subjects.
2002 Jan
Effect of parecoxib, a novel intravenous cyclooxygenase type-2 inhibitor, on the postoperative opioid requirement and quality of pain control.
2002 Jun
Intravenous parecoxib sodium foracute pain after orthopedic knee surgery.
2002 Jun
[Control of postoperative pain. First COX-2 inhibitor for injection].
2002 Jun 27
Evaluation of efficacy, safety and tolerability of valdecoxib in osteo-arthritis patients--an Indian study.
2002 Nov
COX-2 inhibitors and their role in gynecology.
2002 Nov
The effects of cyclooxygenase isozyme inhibition on incisional wound healing in mouse skin.
2002 Nov
[Pharmacology of cyclooxygenase 2 inhibition].
2003
The second generation of COX-2 inhibitors: what advantages do the newest offer?
2003
The role of cyclooxygenase selective inhibitors in the gastrointestinal tract.
2003 Dec
Clinical pharmacology of etoricoxib: a novel selective COX2 inhibitor.
2003 Feb
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
Efficacy and safety of the first parenteral selective COX-2 inhibitor, parecoxib sodium, in adult patients with postoperative pain.
2003 Jul
Gateways to clinical trials.
2003 Jun
[Progress in therapy of rheumatism. New coxib works especially fast].
2003 Jun 5
Gateways to clinical trials. March 2003.
2003 Mar
[Adverse effect-free analgesia. New COX-2 inhibitor is even more selective].
2003 May 1
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
Stability of reconstituted parecoxib for injection with commonly used diluents.
2003 Oct
Expression of cyclooxygenase isozymes during morphogenesis and cycling of pelage hair follicles in mouse skin: precocious onset of the first catagen phase and alopecia upon cyclooxygenase-2 overexpression.
2003 Oct
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
Selective cyclo-oxygenase-2 inhibition with parecoxib acutely impairs endothelium-dependent vasodilatation in patients with essential hypertension.
2003 Sep
Gateways to clinical trials.
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
[Review of analgesics].
2004 Dec
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
Differential effects of selective COX-2 inhibitors on cell cycle regulation and proliferation of glioblastoma cell lines.
2004 Jan
Anti-hyperalgesic activity of the cox-2 inhibitor lumiracoxib in a model of bone cancer pain in the rat.
2004 Jan
Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations.
2004 Jul
Parecoxib: new preparation. A NSAID for postoperative pain: no proven advantage.
2004 Jun
Gateways to clinical trials.
2004 Mar
Collision-induced dissociation of valdecoxib metabolites: a novel rearrangement involving an isoxazole ring.
2004 Mar
Patients' global evaluation of analgesia and safety of injected parecoxib for postoperative pain: a quantitative systematic review.
2004 Sep
[Use of low molecular weight heparin (Clexane) together with selective COX-2 inhibitor (Dynastat--once or twice per day)].
2005
Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance.
2005
COX-2 inhibition prevents downregulation of key renal water and sodium transport proteins in response to bilateral ureteral obstruction.
2005 Aug
Cyclooxygenase-2 plays a central role in the genesis of pancreatitis and associated lung injury.
2005 Feb
Cardiovascular issues of COX-2 inhibitors and NSAIDs.
2005 Nov
Increased risk of cardiovascular events with parecoxib/valdecoxib: a systematic review and meta-analysis.
2005 Nov 25
The antinociceptive effect of local or systemic parecoxib combined with lidocaine/clonidine intravenous regional analgesia for complex regional pain syndrome type I in the arm.
2005 Sep
Analgesic synergism between intrathecal morphine and cyclooxygenase-2 inhibitors in mice.
2005 Sep
Single dose parecoxib significantly improves ventilatory function in early extubation coronary artery bypass surgery: a prospective randomized double blind placebo controlled trial.
2006 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: intravenously (IV) or intramuscularly (IM)
The recommended dose is 40 mg administered intravenously (IV) or intramuscularly (IM), followed every 6 to 12 hours by 20 mg or 40 mg as required, not to exceed 80 mg/day.
Route of Administration: Parenteral
100 uM parecoxib inhibited rat osteoclast differentiation by 94%
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:57:42 GMT 2023
Edited
by admin
on Fri Dec 15 15:57:42 GMT 2023
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
SC-65872
Code English
VALDYN
Brand Name English
VALDECOXIB [MART.]
Common Name English
VALDECOXIB [VANDF]
Common Name English
Valdecoxib [WHO-DD]
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 Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
WHO-ATC M01AH03
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
EMA ASSESSMENT REPORTS BEXTRA (WITHDRAWN: DYSMENORRHEA)
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
EMA ASSESSMENT REPORTS VALDYN (WITHDRAWN: DYSMENORRHEA)
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
EMA ASSESSMENT REPORTS BEXTRA (WITHDRAWN: OSTEOARTHRITIS)
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
EMA ASSESSMENT REPORTS VALDYN (WITHDRAWN: OSTEOARTHRITIS)
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
EMA ASSESSMENT REPORTS BEXTRA (WITHDRAWN: ARTHRITIS, RHEUMATOID)
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
WHO-VATC QM01AH03
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
Code System Code Type Description
DRUG BANK
DB00580
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
HSDB
7302
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
MERCK INDEX
m11356
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2799
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
INN
7815
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
NCI_THESAURUS
C1869
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
EVMPD
SUB05065MIG
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
LACTMED
Valdecoxib
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
WIKIPEDIA
VALDECOXIB
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
CHEBI
63634
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
CAS
181695-72-7
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID6044226
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
USAN
KK-41
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL865
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
NSC
759846
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
PUBCHEM
119607
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
RXCUI
278567
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY RxNorm
FDA UNII
2919279Q3W
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
SMS_ID
100000085238
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
MESH
C406224
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
IUPHAR
2894
Created by admin on Fri Dec 15 15:57:42 GMT 2023 , Edited by admin on Fri Dec 15 15:57:42 GMT 2023
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL; URINE
TARGET -> INHIBITOR
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
Related Record Type Details
METABOLITE ACTIVE -> PARENT
MINOR
URINE
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
URINE
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
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 -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE ACTIVE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
MAJOR
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