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-2 189 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15494548	Inhibitor 7728		0.005 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 151 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Palliative	Withdrawn	BEXTRA Approved Use BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis.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 1.00586881E12
Rheumatoid arthritis 294 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf	Palliative	Withdrawn	BEXTRA Approved Use BEXTRA Tablets are indicated: For relief of the signs and symptoms of osteoarthritis and adult rheumatoid arthritis.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 1.00586881E12
Primary dysmenorrhea 12 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 1.00586881E12

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 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P2.pdf Page: p.28	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 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: https://pubmed.ncbi.nlm.nih.gov/17133774 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: https://pubmed.ncbi.nlm.nih.gov/17133774 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: https://pubmed.ncbi.nlm.nih.gov/17133774 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf Page: p.71	unhealthy n = 430 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 430 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf 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: https://ec.europa.eu/health/documents/community-register/2005/200501269150/anx_9150_en.pdf Page: p.3	unhealthy Health Status: unhealthy Condition: Osteoarthritis \| Adult rheumatoid arthritis Sources: https://ec.europa.eu/health/documents/community-register/2005/200501269150/anx_9150_en.pdf 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: https://ec.europa.eu/health/documents/community-register/2005/200501269150/anx_9150_en.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Osteoarthritis \| Adult rheumatoid arthritis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf Page: p.1, 9	unhealthy Health Status: unhealthy Condition: Osteoarthritis \| Adult rheumatoid arthritis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf Page: p.1, 9	Other AEs: Erythema multiforme... Other AEs: Erythema multiforme (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf Page: p.9	unhealthy Health Status: unhealthy Condition: Osteoarthritis \| Adult rheumatoid arthritis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf Page: p.9	Other AEs: Anaphylactic reaction, Angioedema... Other AEs: Anaphylactic reaction Angioedema Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf Page: p.70	unhealthy n = 1114 Health Status: unhealthy Condition: Rheumatoid arthritis Sex: M+F Population Size: 1114 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf Page: p.69	unhealthy n = 430 Health Status: unhealthy Condition: Arthritis Sex: M+F Population Size: 430 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_medr_P3.pdf Page: p.69

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1601 inhibitor 1467	substrate 936 inhibitor 1604	substrate 1118 inhibitor 1702

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1325 CYP1A2 1383 CYP2E1 790 OAT1 554 OAT3 588	CYP2C19 910 CYP1A2 972 UGT 173

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
CYP2E1 871	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
OAT1 558	inhibitor 3045 Sources: https://www.jstage.jst.go.jp/article/dmpk/advpub/0/advpub_DMPK-10-RG-048/_pdf/-char/ja#page=11 Page: 11.0	no
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 1
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 1
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 1
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 1
OAT3 590	inhibitor 3045 Sources: https://www.jstage.jst.go.jp/article/dmpk/advpub/0/advpub_DMPK-10-RG-048/_pdf/-char/ja#page=11 Page: 11.0	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C19 910	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	major
CYP3A4 1601	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	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: 12.0
CYP1A2 972	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	minor
CYP2C9 936	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	yes
CYP2D6 1118	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	yes
UGT 173	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=13 Page: 13.0	yes
UGT 173	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=36 Page: 36.0	yes	SC-66905 1

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63634	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63634
ChemicalBook	CB4754453	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4754453
MolPort	MolPort-000-883-874	https://www.molport.com/shop/molecule-link/MolPort-000-883-874
Selleck Chemicals	valdecoxib	http://www.selleckchem.com/products/valdecoxib.html
ZINC	ZINC000000006694	http://zinc15.docking.org/substances/ZINC000000006694
eMolecules	877479	https://www.emolecules.com/cgi-bin/more?vid=877479

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
Parecoxib (parecoxib sodium).	2001	11465874
A three-step kinetic mechanism for selective inhibition of cyclo-oxygenase-2 by diarylheterocyclic inhibitors.	2001 Aug 1	11463341
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
Upper gastrointestinal safety evaluation of parecoxib sodium, a new parenteral cyclooxygenase-2-specific inhibitor, compared with ketorolac, naproxen, and placebo.	2001 Sep	11589257
The injectable cyclooxygenase-2-specific inhibitor parecoxib sodium has analgesic efficacy when administered preoperatively.	2001 Sep	11524347
Etoricoxib.	2002	12466002
Development and clinical application of COX-2-selective inhibitors for the treatment of osteoarthritis and rheumatoid arthritis.	2002	12086294
Selecting new drugs for pain control: evidence-based decisions or clinical impressions?	2002 Aug	12198983
Efficacy and safety of intravenous parecoxib sodium in relieving acute postoperative pain following gynecologic laparotomy surgery.	2002 Aug	12151917
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
Effects of parecoxib, a parenteral COX-2-specific inhibitor, on the pharmacokinetics and pharmacodynamics of propofol.	2002 Jan	11753007
Randomized placebo-controlled trial comparing efficacy and safety of valdecoxib with naproxen in patients with osteoarthritis.	2002 Jun	12100776
Nonsteroidal anti-inflammatory drugs, coxibs, and cardio-renal physiology: a mechanism-based approach.	2002 Mar 21	11909554
Valdecoxib is more efficacious than rofecoxib in relieving pain associated with oral surgery.	2002 Mar-Apr	11897923
The analgesic efficacy of valdecoxib vs. oxycodone/acetaminophen after oral surgery.	2002 May	12036167
Evaluation of efficacy, safety and tolerability of valdecoxib in osteo-arthritis patients--an Indian study.	2002 Nov	12797647
The influence of parecoxib, a parenteral cyclooxygenase-2 specific inhibitor, on the pharmacokinetics and clinical effects of midazolam.	2002 Sep	12198057
Disposition of a specific cyclooxygenase-2 inhibitor, valdecoxib, in human.	2002 Sep	12167567
[Pharmacology of cyclooxygenase 2 inhibition].	2003	12705061
[Coxibs: highly selective cyclooxygenase-2 inhibitors. Part II. Side effects].	2003 Apr	12868201
The role of cyclooxygenase selective inhibitors in the gastrointestinal tract.	2003 Dec	14602052
The COX-2 specific inhibitor, valdecoxib, is an effective, opioid-sparing analgesic in patients undergoing total knee arthroplasty.	2003 Feb	12590029
Review article: The pharmacological properties and clinical use of valdecoxib, a new cyclo-oxygenase-2-selective inhibitor.	2003 Feb 15	12622757
Gateways to clinical trials.	2003 Jan-Feb	12690708
Efficacy and safety of the first parenteral selective COX-2 inhibitor, parecoxib sodium, in adult patients with postoperative pain.	2003 Jul	14748383
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
Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population.	2003 Jul-Aug	12911075
Gateways to clinical trials. March 2003.	2003 Mar	12731460
Gateways to clinical trials.	2003 May	12808477
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
Development and validation of an automated SPE-LC-MS/MS assay for valdecoxib and its hydroxylated metabolite in human plasma.	2003 Sep 15	12946532
Clinical pharmacology of novel selective COX-2 inhibitors.	2004	14965322
Effective treatment of laparoscopic cholecystectomy pain with intravenous followed by oral COX-2 specific inhibitor.	2004 Feb	14742366
S-adenosyl methionine (SAMe) versus celecoxib for the treatment of osteoarthritis symptoms: a double-blind cross-over trial. [ISRCTN36233495].	2004 Feb 26	15102339
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.	2004 Jan	14996519
Unexpected nanomolar inhibition of carbonic anhydrase by COX-2-selective celecoxib: new pharmacological opportunities due to related binding site recognition.	2004 Jan 29	14736236
Collision-induced dissociation of valdecoxib metabolites: a novel rearrangement involving an isoxazole ring.	2004 Mar	15039937
Valdecoxib versus rofecoxib in acute postsurgical pain: results of a randomized controlled trial.	2004 May	15120774
Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic.	2004 May	15117884
Parecoxib sodium, an injectable COX-2-specific inhibitor, does not affect unfractionated heparin-regulated blood coagulation parameters.	2004 May	15102867
A systematic review of COX-2 inhibitors compared with traditional NSAIDs, or different COX-2 inhibitors for post-operative pain.	2004 May	15101847

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. Primary Dysmenorrhea: the recommended dose of BEXTRA Tablets for treatment of primary dysmenorrhea is 20 mg twice daily, as needed.

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)