ROFECOXIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H14O4S
Molecular Weight	314.356
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3

InChI

InChIKey=RZJQGNCSTQAWON-UHFFFAOYSA-N

InChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3

HIDE SMILES / InChI

Molecular Formula	C17H14O4S
Molecular Weight	314.356
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/2016/021042s033,021052s024lbl.pdf | http://www.fda.gov/drugs/drugsafety/postmarketdrugsafetyinformationforpatientsandproviders/ucm106290.htm

Rofecoxib is a nonsteroidal anti-inflammatory drug which selectively inhibits COX-2 and subsequent prostaglandin synthesis. The drug was developed by Merk and approved by FDA in 1999 for relief of signs and symptoms of arthritis, acute pain in adults, and painful menstrual cycles under the name Vioxx. Later on Merck voluntarily withdrawn Vioxx from the market due to safety concerns (high risk of heart attack and stroke).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 192 Target ID: CHEMBL230 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Inhibitor 8228		0.02 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Hemophilic Arthropathy 1 Sources: https://adisinsight.springer.com/drugs/800050774 https://www.mdedge.com/rheumatology/article/152669/bleeding-disorders/fda-grants-orphan-drug-status-rofecoxib-hemophilic	Primary	Phase II 1144	Unknown Approved Use Unknown
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Palliative	Withdrawn	VIOXX Approved Use For relief of the signs and symptoms of osteoarthritis, rheumatoid arthritis in adults, pauciarticular or polyarticular course Juvenile Rheumatoid Arthritis (JRA) in patients 2 years and older and who weigh 10 kg (22 lbs) or more, for the management of acute pain in adults, for the treatment of primary dysmenorrhea, for the acute treatment of migraine attacks with or without aura in adults. Launch Date 9.2715837E11
Rheumatoid arthritis 313 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Palliative	Withdrawn	VIOXX Approved Use For relief of the signs and symptoms of osteoarthritis, rheumatoid arthritis in adults, pauciarticular or polyarticular course Juvenile Rheumatoid Arthritis (JRA) in patients 2 years and older and who weigh 10 kg (22 lbs) or more, for the management of acute pain in adults, for the treatment of primary dysmenorrhea, for the acute treatment of migraine attacks with or without aura in adults. Launch Date 9.2715837E11
Acute pain 17 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Primary	Withdrawn	VIOXX Approved Use For relief of the signs and symptoms of osteoarthritis, rheumatoid arthritis in adults, pauciarticular or polyarticular course Juvenile Rheumatoid Arthritis (JRA) in patients 2 years and older and who weigh 10 kg (22 lbs) or more, for the management of acute pain in adults, for the treatment of primary dysmenorrhea, for the acute treatment of migraine attacks with or without aura in adults. Launch Date 9.2715837E11
Primary dysmenorrhea 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Primary	Withdrawn	VIOXX Approved Use For relief of the signs and symptoms of osteoarthritis, rheumatoid arthritis in adults, pauciarticular or polyarticular course Juvenile Rheumatoid Arthritis (JRA) in patients 2 years and older and who weigh 10 kg (22 lbs) or more, for the management of acute pain in adults, for the treatment of primary dysmenorrhea, for the acute treatment of migraine attacks with or without aura in adults. Launch Date 9.2715837E11
Migraine 103 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Primary	Withdrawn	VIOXX Approved Use For relief of the signs and symptoms of osteoarthritis, rheumatoid arthritis in adults, pauciarticular or polyarticular course Juvenile Rheumatoid Arthritis (JRA) in patients 2 years and older and who weigh 10 kg (22 lbs) or more, for the management of acute pain in adults, for the treatment of primary dysmenorrhea, for the acute treatment of migraine attacks with or without aura in adults. Launch Date 9.2715837E11

C_max

Value	Dose	Co-administered	Analyte	Population
321 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ROFECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4018 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ROFECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
17 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ROFECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
13% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		ROFECOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12.5 mg 1 times / day steady, oral Recommended Dose: 12.5 mg, 1 times / day Route: oral Route: steady Dose: 12.5 mg, 1 times / day Co-administed with:: Gefitinib(250 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/	unhealthy, 44-76 years n = 6 Health Status: unhealthy Condition: non small-cell lung cancer Age Group: 44-76 years Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/	Disc. AE: Renal impairment... AEs leading to discontinuation/dose reduction: Renal impairment (grade 1, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/
50 mg 1 times / day steady, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: steady Dose: 50 mg, 1 times / day Co-administed with:: Gefitinib(250 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/	unhealthy, 44-76 years n = 33 Health Status: unhealthy Condition: non small-cell lung cancer Age Group: 44-76 years Sex: M+F Population Size: 33 Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/	Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/
25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/	unhealthy, 58–71years n = 1167 Health Status: unhealthy Condition: colorectal cancer Age Group: 58–71years Sex: M+F Population Size: 1167 Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/	Disc. AE: Cardiac thrombosis... Other AEs: Cardiac thrombosis... AEs leading to discontinuation/dose reduction: Cardiac thrombosis (grade 5, 4 patients) Other AEs: Cardiac thrombosis (16 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/
25 mg 1 times / day multiple, oral (max) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/	unhealthy, 66.8 years n = 2896 Health Status: unhealthy Condition: painful osteoarthritis of the knee or hip Age Group: 66.8 years Sex: M+F Population Size: 2896 Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/	Disc. AE: Dyspepsia, Nausea... AEs leading to discontinuation/dose reduction: Dyspepsia (4.4%) Nausea (2.4%) Dizziness (2.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/
25 mg 1 times / day multiple, oral (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	Disc. AE: Death... Other AEs: Hemorrhage, Edema... AEs leading to discontinuation/dose reduction: Death (grade 5, 1653 patients) Other AEs: Hemorrhage (3915 patients) Edema (3677 patients) Thrombosis (1917 patients) Embolism (233 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/

AEs

AE	Significance	Dose	Population
Renal impairment	grade 1, 1 patient Disc. AE	12.5 mg 1 times / day steady, oral Recommended Dose: 12.5 mg, 1 times / day Route: oral Route: steady Dose: 12.5 mg, 1 times / day Co-administed with:: Gefitinib(250 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/	unhealthy, 44-76 years n = 6 Health Status: unhealthy Condition: non small-cell lung cancer Age Group: 44-76 years Sex: M+F Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/17664473/
Cardiac thrombosis	16 patients	25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/	unhealthy, 58–71years n = 1167 Health Status: unhealthy Condition: colorectal cancer Age Group: 58–71years Sex: M+F Population Size: 1167 Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/
Cardiac thrombosis	grade 5, 4 patients Disc. AE	25 mg 1 times / day steady, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/	unhealthy, 58–71years n = 1167 Health Status: unhealthy Condition: colorectal cancer Age Group: 58–71years Sex: M+F Population Size: 1167 Sources: https://pubmed.ncbi.nlm.nih.gov/17652651/
Dizziness	2.1% Disc. AE	25 mg 1 times / day multiple, oral (max) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/	unhealthy, 66.8 years n = 2896 Health Status: unhealthy Condition: painful osteoarthritis of the knee or hip Age Group: 66.8 years Sex: M+F Population Size: 2896 Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/
Nausea	2.4% Disc. AE	25 mg 1 times / day multiple, oral (max) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/	unhealthy, 66.8 years n = 2896 Health Status: unhealthy Condition: painful osteoarthritis of the knee or hip Age Group: 66.8 years Sex: M+F Population Size: 2896 Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/
Dyspepsia	4.4% Disc. AE	25 mg 1 times / day multiple, oral (max) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/	unhealthy, 66.8 years n = 2896 Health Status: unhealthy Condition: painful osteoarthritis of the knee or hip Age Group: 66.8 years Sex: M+F Population Size: 2896 Sources: https://pubmed.ncbi.nlm.nih.gov/12495363/
Thrombosis	1917 patients	25 mg 1 times / day multiple, oral (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/
Embolism	233 patients	25 mg 1 times / day multiple, oral (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/
Edema	3677 patients	25 mg 1 times / day multiple, oral (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/
Hemorrhage	3915 patients	25 mg 1 times / day multiple, oral (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/
Death	grade 5, 1653 patients Disc. AE	25 mg 1 times / day multiple, oral (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/	unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: https://pubmed.ncbi.nlm.nih.gov/19453292/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 768 inhibitor 1579	inhibitor 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 781 CYP2E1 876	UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A8 283 UGT1A9 380 UGT2B7 389 UGT2B15 203

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP3A4 1909	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21042lbl.pdf#page=4 Page: 4.0	likely	weak (co-administration study) Comment: A 30% interactions, additional studies would be necessary reduction of the AUC of the CYP3A4 substrate to more completely elucidate the drug interaction midazolam was observed with rofecoxib 25mg profile of rofecoxib and determine the clinical rele- daily. This reduction is most probably due to in- vance of any possible interactions. creased first-pass metabolism through induction of intestinal CYP3A4 by rofecoxib Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/21042lbl.pdf#page=4 Page: 4.0
CYP2C9 1803	inhibitor 3240 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
CYP2D6 1875	inhibitor 3240 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
CYP2E1 964	inhibitor 3240 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
CYP3A4 1909	inhibitor 3240 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
OATP1B1 796	inhibitor 3240 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3894639/	yes [IC50 1.17 uM]

Drug as victim

Target	Modality	Activity	Metabolite
UGT2B15 203	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/	major	5-hydroxyrofecoxib 1
UGT1A1 418	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A3 422	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A4 347	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A6 307	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A8 283	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A9 380	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/	yes	5-hydroxyrofecoxib 1
UGT2B7 389	substrate 3326 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/	yes	5-hydroxyrofecoxib 1

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8887	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8887
ChemicalBook	CB6327130	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6327130
MolPort	MolPort-000-883-878	https://www.molport.com/shop/molecule-link/MolPort-000-883-878
MolPort	MolPort-006-817-786	https://www.molport.com/shop/molecule-link/MolPort-006-817-786
Selleck Chemicals	rofecoxib-vioxx	http://www.selleckchem.com/products/rofecoxib-vioxx.html
ZINC	ZINC000000007455	http://zinc15.docking.org/substances/ZINC000000007455
eMolecules	877485	https://www.emolecules.com/cgi-bin/more?vid=877485

PubMed

Title	Date	PubMed
Effect of local application of growth factors on gastric ulcer healing and mucosal expression of cyclooxygenase-1 and -2.	2001	11549833
[Selective cyclooxygenase 2 inhibitors (COX-2)].	2001	11468975
Potential adverse effects of cyclooxygenase-2 inhibition: evidence from animal models of inflammation.	2001	11437671
Apoptosis signaling pathways mediated by cyclooxygenase-2 inhibitors in prostate cancer cells.	2001	11384747
A multicenter, randomized, controlled trial to evaluate the safety profile, tolerability, and efficacy of rofecoxib in advanced elderly patients with osteoarthritis.	2001 Apr	11405384
[The coxibs, third generation anti-inflammatories].	2001 Apr	11388024
Gastrointestinal damage induced by celecoxib and rofecoxib in rats.	2001 Apr	11330413
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.	2001 Apr	11315375
Cyclo-oxygenase and lipoxygenase pathways in mast cell dependent-neurogenic inflammation induced by electrical stimulation of the rat saphenous nerve.	2001 Apr	11264253
Effects of COX-2 inhibitors on aortic prostacyclin production in cholesterol-fed rabbits.	2001 Aug	11472739
Selective and rapid liquid chromatography-mass spectrometry method for the quantification of rofecoxib in pharmacokinetic studies with humans.	2001 Aug 25	11522069
Design and synthesis of celecoxib and rofecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of sulfonamide and methylsulfonyl pharmacophores by an azido bioisostere.	2001 Aug 30	11520213
Safety of a specific COX-2 inhibitor in aspirin-induced asthma.	2001 Feb	11251623
The selective cyclooxygenase-2 inhibitor rofecoxib reduces kainate-induced cell death in the rat hippocampus.	2001 Feb	11168565
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2.	2001 Feb	11160644
FDA refuses companies' request to drop ulcer warning.	2001 Feb 17	11179151
Efficacy of single-dose and multidose rofecoxib in the treatment of post-orthopedic surgery pain.	2001 Jan	11198829
Effect of rofecoxib on the pharmacokinetics of digoxin in healthy volunteers.	2001 Jan	11144988
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans.	2001 Jan	11136272
[Stomach-saving "Coxibs". No reason for therapeutic risks].	2001 Jan 18	11215349
Renal effects of COX-2-selective inhibitors.	2001 Jan-Feb	11275626
Economic evaluation of rofecoxib versus nonselective nonsteroidal anti-inflammatory drugs for the treatment of osteoarthritis.	2001 Jul	11519771
Cyclooxygenase (COX-2) selective inhibitors. Any better than NSAIDs?	2001 Jul	11494927
Induction of delayed follicular rupture in the human by the selective COX-2 inhibitor rofecoxib: a randomized double-blind study.	2001 Jul	11425807
[Safety of specific cyclo-oxygenase 2 inhibitors].	2001 Jul 28	11503322
Rofecoxib-induced renal dysfunction in a patient with compensated cirrhosis and heart failure.	2001 Jun	11419859
Cyclooxygenase-1 vs. cyclooxygenase-2 inhibitors in the induction of antinociception in rodent withdrawal reflexes.	2001 Jun	11378164
Classic NSAID and selective cyclooxygenase (COX)-1 and COX-2 inhibitors in healing of chronic gastric ulcers.	2001 Jun 1	11376495
[Selective COX-2 inhibitor. Stomach protection--but not always].	2001 Jun 21	11469005
Cyclooxygenase-2 inhibition and renal function.	2001 Jun 5	11388825
[Results of the VIGOR study. Rofecoxib halves the complication rate].	2001 Jun 7	11460417
[Therapy of arthrosis. Life threatening gastrointestinal events can be reduced].	2001 Jun 7	11460416
Preoperative oral rofecoxib does not decrease postoperative pain or morphine consumption in patients after radical prostatectomy: a prospective, randomized, double-blinded, placebo-controlled trial.	2001 Mar	11331167
Osteoarthritis management: the role of cyclooxygenase-2-selective inhibitors.	2001 Mar	11318071
Is rofecoxib safer than naproxen?	2001 Mar	11252204
Where is the evidence that cyclooxygenase inhibition is the primary cause of nonsteroidal anti-inflammatory drug (NSAID)-induced gastrointestinal injury? Topical injury revisited.	2001 Mar 15	11266647
Cyclooxygenase-2--specific inhibitors and cardiorenal function: a randomized, controlled trial of celecoxib and rofecoxib in older hypertensive osteoarthritis patients.	2001 Mar-Apr	11304662
[The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%].	2001 May	11413920
EULAR recommendations for the management of knee osteoarthritis.	2001 May	11345080
[Clinical use of COX-2 inhibitors].	2001 May-Jun	11548555
COX-1 and COX-2 inhibitors.	2001 Oct	11566042
Tolerability to new COX-2 inhibitors in NSAID-sensitive patients with cutaneous reactions.	2001 Sep	11570615
Tolerability of rofecoxib.	2001 Sep	11551261
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves.	2001 Sep 21	11567657
How safe are your prescription pills?	2001 Sep 3	11550614
Celecoxib- and rofecoxib-induced delirium.	2001 Spring	11449042

Patents

Sample Use Guides

In Vivo Use Guide

Osteoarthritis: the recommended starting dose of rofecoxib (VIOXX) is 12.5 mg once daily. Rheumatoid Arthritis: the recommended dose is 50 mg once daily. Management of Acute Pain and Treatment of Primary Dysmenorrhea: the recommended dose is 50 mg once daily. Acute Treatment of Migraine Attacks with or without aura: the recommended dose is 25 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

THP-1 human macrophages and peripheral blood mononuclear cells were incubated with rofecoxib (at 5, 10, 25 uM). The presence of rofecoxib (at high concentrations) significantly decreased expression of 27-hydroxylase and ABCA1, interfering with normal cholesterol outflow from macrophages.

Substance Class	Chemical Created by `admin` on `Thu Jul 06 22:00:26 UTC 2023` Edited by `admin` on `Thu Jul 06 22:00:26 UTC 2023`
Record UNII	0QTW8Z7MCR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROFECOXIB

Official Name

English

NSC-758705

Code

English

rofecoxib [INN]

Common Name

English

MK-966

Code

English

TRM-201

Code

English

VIOXX

Brand Name

English

M01AH02

Code

English

ROFECOXIB [MI]

Common Name

English

NSC-720256

Code

English

ROFECOXIB [MART.]

Common Name

English

ROFECOXIB [USAN]

Common Name

English

MK-0966

Code

English

MK0966

Code

English

TRM201

Code

English

ROFECOXIB [VANDF]

Common Name

English

Rofecoxib [WHO-DD]

Common Name

English

4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone

Systematic Name

English

ROFECOXIB [ORANGE BOOK]

Common Name

English

ROFECOXIB [JAN]

Common Name

English

4-(P-(METHYLSULFONYL)PHENYL)-3-PHENYL-2(5H)-FURANONE

Common Name

English

ROFECOXIB [HSDB]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM01AH02