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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
0.0050000000000000001 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

1005868800000
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

1005868800000
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

1005868800000
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:
unhealthy, 18-92
Health Status: unhealthy
Age Group: 18-92
Sex: M+F
Sources:
Other AEs: Gastrointestinal ulcer haemorrhage...
Other AEs:
Gastrointestinal ulcer haemorrhage (significant, 0.48%)
Sources:
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:
unhealthy, 32.3 ±10.9
Health Status: unhealthy
Age Group: 32.3 ±10.9
Sex: M+F
Sources:
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:
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:
unhealthy
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:
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:
unhealthy
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:
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:
unhealthy
Other AEs: Anaphylactic reaction, Angioedema...
Other AEs:
Anaphylactic reaction
Angioedema
Sources:
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:
unhealthy
Other AEs: Erythema multiforme...
Other AEs:
Erythema multiforme (grade 3-5)
Sources:
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:
unhealthy
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:
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
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:
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:
unhealthy
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:
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:
unhealthy, 18-92
Health Status: unhealthy
Age Group: 18-92
Sex: M+F
Sources:
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:
unhealthy, 32.3 ±10.9
Health Status: unhealthy
Age Group: 32.3 ±10.9
Sex: M+F
Sources:
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:
unhealthy, 32.3 ±10.9
Health Status: unhealthy
Age Group: 32.3 ±10.9
Sex: M+F
Sources:
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:
unhealthy, 32.3 ±10.9
Health Status: unhealthy
Age Group: 32.3 ±10.9
Sex: M+F
Sources:
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:
unhealthy, 32.3 ±10.9
Health Status: unhealthy
Age Group: 32.3 ±10.9
Sex: M+F
Sources:
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Halitosis 0.3%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Gastroenteritis 1.2%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Peripheral edema 2.2%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Abdominal pain 5.5%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Dyspepsia 6.2%
Disc. AE
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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
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
The biochemical selectivity of novel COX-2 inhibitors in whole blood assays of COX-isozyme activity.
2002
Valdecoxib.
2002
Development and clinical application of COX-2-selective inhibitors for the treatment of osteoarthritis and rheumatoid arthritis.
2002
COX-2-selective inhibitors in the treatment of arthritis.
2002
Valdecoxib (Bextra)--a new cox-2 inhibitor.
2002 Apr 29
Valdecoxib, a cyclooxygenase-2-specific inhibitor, is effective in treating primary dysmenorrhea.
2002 Aug
Gateways to clinical trials.
2002 Dec
Valdecoxib (Pharmacia).
2002 Feb
Valdecoxib does not impair platelet function.
2002 Jul
The analgesic efficacy of valdecoxib vs. oxycodone/acetaminophen after oral surgery.
2002 May
The effects of cyclooxygenase isozyme inhibition on incisional wound healing in mouse skin.
2002 Nov
Incidence of gastroduodenal ulcers associated with valdecoxib compared with that of ibuprofen and diclofenac in patients with osteoarthritis.
2002 Oct
Gateways to Clinical Trials.
2002 Sep
A single preoperative oral dose of valdecoxib, a new cyclooxygenase-2 specific inhibitor, relieves post-oral surgery or bunionectomy pain.
2002 Sep
Efficacy and safety of valdecoxib in treating the signs and symptoms of rheumatoid arthritis: a randomized, controlled comparison with placebo and naproxen.
2002 Sep
[Adverse effects of NSAID are insidious. No pain--despite life threatening gastric hemorrhage].
2002 Sep 12
Valdecoxib.
2002 Summer
Determination of valdecoxib and its metabolites in human urine by automated solid-phase extraction-liquid chromatography-tandem mass spectrometry.
2003 Feb 25
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
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
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
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
Quantitation of Valdecoxib in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection using liquid-liquid extraction.
2004 Apr 5
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor.
2004 Feb
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.
2004 Jan
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride.
2004 Jan 19
Gateways to clinical trials.
2004 Mar
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.
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