VALDECOXIB

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf | http://www.rotlaw.com/legal-library/bextra-valdecoxib/

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 188 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15494548	Inhibitor 7701	Osteoarthritis Rheumatoid arthritis	0.0050000000000000001 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 152 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Palliative	Cyclooxygenase-2	Withdrawn	BEXTRA Approved Use BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis.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
Rheumatoid arthritis 294 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Palliative	Cyclooxygenase-2	Withdrawn	BEXTRA Approved Use BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis.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 dysmenorrhea 14 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Primary		Withdrawn	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

C_max

Value	Dose	Analyte	Population
161.1 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341se8-003_bextra_lbl.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VALDECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1385 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16599270/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	VALDECOXIB serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.8 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	1-HYDROXYVALDECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1479 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341se8-003_bextra_lbl.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	VALDECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
9062 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16599270/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	VALDECOXIB serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
15 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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 OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.11 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341se8-003_bextra_lbl.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VALDECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16599270/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		VALDECOXIB serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341se8-003_bextra_lbl.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		VALDECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P2.pdf	unhealthy, 18-92 Health Status: unhealthy Age Group: 18-92 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P2.pdf	Other AEs: Gastrointestinal ulcer haemorrhage... Other AEs: Gastrointestinal ulcer haemorrhage (significant, 0.48%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P2.pdf
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: https://pubmed.ncbi.nlm.nih.gov/17133774	unhealthy, 32.3 ±10.9 Health Status: unhealthy Age Group: 32.3 ±10.9 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17133774	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: https://pubmed.ncbi.nlm.nih.gov/17133774
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf
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: https://ec.europa.eu/health/documents/community-register/2005/200501269150/anx_9150_en.pdf	unhealthy Health Status: unhealthy Sources: https://ec.europa.eu/health/documents/community-register/2005/200501269150/anx_9150_en.pdf	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: https://ec.europa.eu/health/documents/community-register/2005/200501269150/anx_9150_en.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Other AEs: Anaphylactic reaction, Angioedema... Other AEs: Anaphylactic reaction Angioedema Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Other AEs: Erythema multiforme... Other AEs: Erythema multiforme (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470 inhibitor 1172	substrate 865 inhibitor 1318	substrate 1038 inhibitor 1421

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1215 CYP1A2 1268 CYP2E1 761 OAT1 547 OAT3 570	CYP2C19 830 CYP1A2 892 UGT 160

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 1406	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	no
CYP2D6 1455	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	no
CYP2E1 841	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	no
CYP3A4 1462	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	no
OAT1 551	inhibitor 2614 Sources: https://www.jstage.jst.go.jp/article/dmpk/advpub/0/advpub_DMPK-10-RG-048/_pdf/-char/ja#page=11 Page: 11	no
CYP2C19 1277	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	yes
CYP2C19 1277	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	yes	SC-66905 1
CYP2C9 1362	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	yes
CYP2C9 1362	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	yes	SC-66905 1
CYP2D6 1455	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	yes	SC-66905 1
CYP3A4 1462	inhibitor 2614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21	yes	SC-66905 1
OAT3 572	inhibitor 2614 Sources: https://www.jstage.jst.go.jp/article/dmpk/advpub/0/advpub_DMPK-10-RG-048/_pdf/-char/ja#page=11 Page: 11	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C19 830	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12	major
CYP3A4 1470	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12	major		yes (co-administration study) Comment: co-administration with ketoconazole or Fluconazole increase VALDECOXIB AUC and Cmax Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12
CYP1A2 892	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12	minor
CYP2C9 865	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12	yes
CYP2D6 1038	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12	yes
UGT 160	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=13 Page: 13	yes
UGT 160	substrate 2752 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=36 Page: 36	yes	SC-66905 1

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63634	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63634
MolPort	MolPort-000-883-874	https://www.molport.com/shop/molecule-link/MolPort-000-883-874
ZINC	ZINC000000006694	http://zinc15.docking.org/substances/ZINC000000006694

PubMed

Title	Date	PubMed
4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2.	2000 Mar 9	10715145
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2.	2001 Feb	11160644
A pharmacokinetic study of intramuscular (i.m.) parecoxib sodium in normal subjects.	2001 Oct	11583480
The biochemical selectivity of novel COX-2 inhibitors in whole blood assays of COX-isozyme activity.	2002	12564662
Valdecoxib.	2002	12269850
Development and clinical application of COX-2-selective inhibitors for the treatment of osteoarthritis and rheumatoid arthritis.	2002	12086294
COX-2-selective inhibitors in the treatment of arthritis.	2002	12086290
Valdecoxib (Bextra)--a new cox-2 inhibitor.	2002 Apr 29	11981510
Valdecoxib, a cyclooxygenase-2-specific inhibitor, is effective in treating primary dysmenorrhea.	2002 Aug	12151162
Gateways to clinical trials.	2002 Dec	12616965
Valdecoxib (Pharmacia).	2002 Feb	12020053
Valdecoxib does not impair platelet function.	2002 Jul	12098171
The analgesic efficacy of valdecoxib vs. oxycodone/acetaminophen after oral surgery.	2002 May	12036167
The effects of cyclooxygenase isozyme inhibition on incisional wound healing in mouse skin.	2002 Nov	12445211
Incidence of gastroduodenal ulcers associated with valdecoxib compared with that of ibuprofen and diclofenac in patients with osteoarthritis.	2002 Oct	12362101
Gateways to Clinical Trials.	2002 Sep	12428432
A single preoperative oral dose of valdecoxib, a new cyclooxygenase-2 specific inhibitor, relieves post-oral surgery or bunionectomy pain.	2002 Sep	12218521
Efficacy and safety of valdecoxib in treating the signs and symptoms of rheumatoid arthritis: a randomized, controlled comparison with placebo and naproxen.	2002 Sep	12209034
[Adverse effects of NSAID are insidious. No pain--despite life threatening gastric hemorrhage].	2002 Sep 12	12380342
Valdecoxib.	2002 Summer	12227215
Determination of valdecoxib and its metabolites in human urine by automated solid-phase extraction-liquid chromatography-tandem mass spectrometry.	2003 Feb 25	12535845
Differential inhibition of fracture healing by non-selective and cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs.	2003 Jul	12798067
[Tolerable pain therapy in rheumatism saves long-term costs. Despite this most COX-2 candidates receive conventional NSAID therapy].	2003 Jul 24	12958786
Gateways to clinical trials.	2003 Jun	12851663
Efficacy and safety of the cyclooxygenase 2 inhibitors parecoxib and valdecoxib in patients undergoing coronary artery bypass surgery.	2003 Jun	12830070
[Progress in therapy of rheumatism. New coxib works especially fast].	2003 Jun 5	12854230
Gateways to clinical trials. March 2003.	2003 Mar	12731460
Gateways to clinical trials.	2003 May	12808477
The COX-2 selective inhibitor, valdecoxib, does not impair platelet function in the elderly: results of a randomized controlled trial.	2003 May	12751271
[Adverse effect-free analgesia. New COX-2 inhibitor is even more selective].	2003 May 1	12808824
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	12810937
Single doses of parecoxib sodium intravenously are as effective as ketorolac in reducing pain after oral surgery.	2003 Sep	12966478
Quantitation of Valdecoxib in human plasma by high-performance liquid chromatography with ultraviolet absorbance detection using liquid-liquid extraction.	2004 Apr 5	15018787
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor.	2004 Feb	14742366
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.	2004 Jan	14996519
Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride.	2004 Jan 19	14698154
Gateways to clinical trials.	2004 Mar	15071612
Collision-induced dissociation of valdecoxib metabolites: a novel rearrangement involving an isoxazole ring.	2004 Mar	15039937
Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters.	2004 May	15102867

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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)