PARECOXIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H18N2O4S
Molecular Weight	370.422
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)NS(=O)(=O)C1=CC=C(C=C1)C2=C(C)ON=C2C3=CC=CC=C3

InChI

InChIKey=TZRHLKRLEZJVIJ-UHFFFAOYSA-N

InChI=1S/C19H18N2O4S/c1-3-17(22)21-26(23,24)16-11-9-14(10-12-16)18-13(2)25-20-19(18)15-7-5-4-6-8-15/h4-12H,3H2,1-2H3,(H,21,22)

HIDE SMILES / InChI

Molecular Formula	C19H18N2O4S
Molecular Weight	370.422
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB08439 | http://www.fda.gov/ohrms/dockets/ac/05/briefing/2005-4090B1_28_CC-FDA-Tab-Q.htmhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21341lbl.pdf | http://www.rotlaw.com/legal-library/bextra-valdecoxib/
Curator's Comment: Description was created based on several sources, including https://www.medicines.org.uk/emc/medicine/8771

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-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15494548	Inhibitor 8297		0.005 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.fda.gov/ohrms/dockets/ac/05/briefing/2005-4090B1_28_CC-FDA-Tab-Q.htm \| https://www.medicines.org.uk/emc/PIL.14519.latest.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/25135338	Inhibitor 8297		5.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pain, postoperative 9 Sources: https://www.medicines.org.uk/emc/PIL.14519.latest.pdf	Palliative	Approved 8429	Dynastat Approved Use Dynastat is used for the short-term treatment of pain in adults after an operation. Launch Date 1.01666882E12
Osteoarthritis 157 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 316 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 16 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 1737 inhibitor 1587	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1478 CYP1A2 1524 CYP2E1 882 OAT1 599 OAT3 642	CYP2C19 991 CYP1A2 1054 UGT 192

Drug as perpetrator

Target	Modality	Activity	Metabolite
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	no
OAT1 603	inhibitor 3277 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 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 3
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 3
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 3
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=21 Page: 21.0	yes	SC-66905 3
OAT3 644	inhibitor 3277 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 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	major
CYP3A4 1737	substrate 3367 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 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	minor
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	yes
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=12 Page: 12.0	yes
UGT 192	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=13 Page: 13.0	yes
UGT 192	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-341_Bextra_biopharmr_P1.pdf#page=36 Page: 36.0	yes	SC-66905 3

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
Parecoxib. Pharmacia corp.	2001 Aug	15973593
[Pharmacology and classification of cyclooxygenase inhibitors].	2004 Apr	15366670
The second generation of COX-2 inhibitors: clinical pharmacological point of view.	2004 Aug	15279595
First and second generations of COX-2 selective inhibitors.	2004 Aug	15279593
[Review of analgesics].	2004 Dec	15669520
Reaction between parecoxib and vecuronium.	2004 Dec	15549999
Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations.	2004 Jul	15335413
The analgesic effects that underlie patient satisfaction with treatment.	2004 Jul	15275801
Parecoxib: new preparation. A NSAID for postoperative pain: no proven advantage.	2004 Jun	15233140
Parecoxib: a shift in pain management?	2004 Mar	15853557
Role of parecoxib in pre-emptive analgesia: comparison of the efficacy and safety of pre- and postoperative parecoxib in patients undergoing general surgery.	2004 May	15636035
The analgesic efficacy of intramuscular parecoxib sodium in postoperative dental pain.	2004 Nov	15622663
A clinical trial demonstrates the analgesic activity of intravenous parecoxib sodium compared with ketorolac or morphine after gynecologic surgery with laparotomy.	2004 Oct	15507939
Presurgical intravenous parecoxib sodium and follow-up oral valdecoxib for pain management after laparoscopic cholecystectomy surgery reduces opioid requirements and opioid-related adverse effects.	2004 Oct	15352969
Parecoxib impairs early tendon repair but improves later remodeling.	2004 Oct-Nov	15494342
Patients' global evaluation of analgesia and safety of injected parecoxib for postoperative pain: a quantitative systematic review.	2004 Sep	15333414
[Use of low molecular weight heparin (Clexane) together with selective COX-2 inhibitor (Dynastat--once or twice per day)].	2005	16313051
Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance.	2005	16168077
Parecoxib: renal failure.	2005 Apr	15877325
Update on cyclooxygenase inhibitors: has a third COX isoform entered the fray?	2005 Aug	16083531
COX-2 inhibition prevents downregulation of key renal water and sodium transport proteins in response to bilateral ureteral obstruction.	2005 Aug	15840770
Cyclooxygenase-2 plays a central role in the genesis of pancreatitis and associated lung injury.	2005 Feb	15730936
Reduction of opioid-related adverse events using opioid-sparing analgesia with COX-2 inhibitors lacks documentation: a systematic review.	2005 Feb	15715611
Severe bronchospasm after parenteral parecoxib: cyclooxygenase-2 inhibitors: not the answer yet.	2005 Feb	15681964
The cyclooxygenase-2-specific inhibitor parecoxib sodium is as effective as 12 mg of morphine administered intramuscularly for treating pain after gynecologic laparotomy surgery.	2005 Feb	15673875
Role of cyclooxygenase-2 in lipopolysaccharide-induced hyperalgesia in formalin test.	2005 Jan	15691066
Selective cyclooxygenase-2 inhibition reverses microcirculatory and inflammatory sequelae of closed soft-tissue trauma in an animal model.	2005 Jan	15634827
Cyclooxygenase-2 is a target of KRASD12, which facilitates the outgrowth of murine C26 colorectal liver metastases.	2005 Jan 1	15671526
Parecoxib, valdecoxib, and cardiovascular risk.	2005 Jan 25	15655125
Pulmonary embolism in a woman taking oral contraceptives and valdecoxib.	2005 Jul	16013893
Prostaglandin-mediated control of rat brain kynurenic acid synthesis--opposite actions by COX-1 and COX-2 isoforms.	2005 Jul	15517427
The meaning of pain relief in a clinical trial.	2005 Jun	15943962
Parecoxib versus ibuprofen.	2005 Mar	15819339
COX-2 inhibitors--a lesson in unexpected problems.	2005 Mar 17	15713947
COX-2 inhibitors--lessons in drug safety.	2005 Mar 17	15713946
Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery.	2005 Mar 17	15713945
[Involvement of L-arginine-nitric oxide-cyclic GMP pathway in the peripheral antinociceptive effect induced by parecoxib].	2005 Mar-Apr	15910705
A randomized, double-blind comparison between parecoxib sodium and propacetamol for parenteral postoperative analgesia after inguinal hernia repair in adult patients.	2005 May	15845675
Changing role of COX-2 inhibitors in the perioperative period: is parecoxib really the answer?	2005 May	15845674
The cardioprotective effects of preconditioning with endotoxin, but not ischemia, are abolished by a peroxisome proliferator-activated receptor-gamma antagonist.	2005 May	15734901
Cardiovascular issues of COX-2 inhibitors and NSAIDs.	2005 Nov	16299629
Effects of intrarenal administration of the cox-2 inhibitor parecoxib during porcine suprarenal aortic cross-clamping.	2005 Nov	16247335
Increased risk of cardiovascular events with parecoxib/valdecoxib: a systematic review and meta-analysis.	2005 Nov 25	16311613
Cancer chemoprevention: lessons learned and future directions.	2005 Oct 3	16160697
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	16115995
Analgesic synergism between intrathecal morphine and cyclooxygenase-2 inhibitors in mice.	2005 Sep	16102800
COX-2 inhibitors and pain after oral surgery - pertinent papers 2002-2003.	2006 Apr	16191457
Constitutive cyclo-oxygenase-2 does not contribute to the development of human visceral pain hypersensitivity.	2006 Aug	16122956
Single dose parecoxib significantly improves ventilatory function in early extubation coronary artery bypass surgery: a prospective randomized double blind placebo controlled trial.	2006 Feb	16361300
Combination therapy using the cyclooxygenase-2 inhibitor Parecoxib and radioimmunotherapy in nude mice with small peritoneal metastases of colonic origin.	2006 Jan	15868166

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

100 uM parecoxib inhibited rat osteoclast differentiation by 94%

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:37:26 UTC 2023` Edited by `admin` on `Fri Dec 15 16:37:26 UTC 2023`
Record UNII	9TUW81Y3CE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PARECOXIB

Official Name

English

PROPANAMIDE, N-((4-(5-METHYL-3-PHENYL-4-ISOXAZOLYL)PHENYL)SULFONYL)-

Systematic Name

English

SC-69124

Code

English

Parecoxib [WHO-DD]

Common Name

English

N-((P-(5-METHYL-3-PHENYL-4-ISOXAZOLYL)PHENYL)SULFONYL)PROPIONAMIDE

Common Name

English

PARECOXIB [USAN]

Common Name

English

parecoxib [INN]

Common Name

English

PARECOXIB [EMA EPAR]

Common Name

English

RAYZON

Brand Name

English

PARECOXIB [MI]

Common Name

English

XAPIT

Brand Name

English

Classification Tree Code System Code

WHO-ATC

M01AH04