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 Later on Merck voluntarily withdrawn Vioxx from the market due to safety concerns (high risk of heart attack and stroke).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-2 196 Target ID: CHEMBL230 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Inhibitor 8297		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 1132	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157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021042s033,021052s024lbl.pdf	Palliative	Withdrawn	VIOXX Approved Use For relief of the signs and symptoms of osteoarthritis, rheumatoid arthritis in adults, pauciarticular or polyarticular course Juvenile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 1999
Rheumatoid arthritis 316 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 1999
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 1999
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 1999
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 1999

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 781 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 788 CYP2E1 882	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 1925	inducer 1573 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 1819	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1517/14656566.1.5.1053 Page: 6.0	no
OATP1B1 803	inhibitor 3277 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 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/	major	5-hydroxyrofecoxib 1
UGT1A1 418	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A3 422	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A4 347	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A6 307	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A8 283	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/ Page: 4.0	weak	5-hydroxyrofecoxib 1
UGT1A9 380	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1885136/	yes	5-hydroxyrofecoxib 1
UGT2B7 389	substrate 3367 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
Alzheimer's disease, inflammation and non-steroidal anti-inflammatory drugs.	2001	11433600
[COX-2 specific inhibitors: are NSAIDs and the stomach become reconcilied?].	2001 Apr	11449148
Rofecoxib as an alternative in aspirin hypersensitivity.	2001 Aug	11488679
Effects of COX-2 inhibitors on aortic prostacyclin production in cholesterol-fed rabbits.	2001 Aug	11472739
Risk of cardiovascular events associated with selective COX-2 inhibitors.	2001 Aug 22-29	11509060
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
[Elderly patient with rheumatoid arthritis. Minimizing the peptic ulcer hemorrhage risk].	2001 Aug 9	11556192
The coxibs, selective inhibitors of cyclooxygenase-2.	2001 Aug 9	11496855
Cyclooxygenase inhibitors: any reservations?	2001 Jan-Feb	11478355
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
Stimulated release of arachidonic acid from rat liver cells by celecoxib and indomethacin.	2001 Jul	11487305
Selective cyclooxygenase-2 inhibitors: a pattern of nephrotoxicity similar to traditional nonsteroidal anti-inflammatory drugs.	2001 Jul	11448662
Lack of cross-reactivity between rofecoxib and aspirin in aspirin-sensitive patients with asthma.	2001 Jul	11447381
Cyclooxygenase-selective inhibition of prostanoid formation: transducing biochemical selectivity into clinical read-outs.	2001 Jul	11435450
Induction of delayed follicular rupture in the human by the selective COX-2 inhibitor rofecoxib: a randomized double-blind study.	2001 Jul	11425807
Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans after the application of cinnamic aldehyde.	2001 Jul	11423836
A new class of COX-2 inhibitors offer an alternative to NSAIDS in pain management after spinal surgery.	2001 Jul 1	11458162
[Safety of specific cyclo-oxygenase 2 inhibitors].	2001 Jul 28	11503322
Ibuprofen to rofecoxib: what does it all mean and what do I do now?	2001 Jul-Aug	11467102
Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine.	2001 Jul-Aug	11433185
[Clinical application of cyclooxygenase-2 inhibitors].	2001 Jun	11503270
Celecoxib-- the debate ranges on.	2001 Jun	11455700
Effect of rofecoxib therapy on measures of health-related quality of life in patients with osteoarthritis.	2001 Jun	11439734
Rofecoxib-induced renal dysfunction in a patient with compensated cirrhosis and heart failure.	2001 Jun	11419859
Acute tubulointerstitial nephritis associated with the selective COX-2 enzyme inhibitor, rofecoxib.	2001 Jun 16	11425419
[Safety of specific cyclo-oxygenase 2 inhibitors].	2001 Jun 2	11414163
[Selective COX-2 inhibitor. Stomach protection--but not always].	2001 Jun 21	11469005
[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
Discovery and design of selective cyclooxygenase-2 inhibitors as non-ulcerogenic, anti-inflammatory drugs with potential utility as anti-cancer agents.	2001 Mar	11465540
Current concepts regarding pharmacologic treatment of rheumatoid and osteoarthritis.	2001 May	11478054
[Clinical use of COX-2 inhibitors].	2001 May-Jun	11548555
[The coxibs, third generation of non-steroidal anti-inflammatory agents].	2001 May-Jun	11508259
LC determination of rofecoxib in bulk and pharmaceutical formulations.	2001 Nov	11516914
COX-1 and COX-2 inhibitors.	2001 Oct	11566042
Influence of risk factors on endoscopic and clinical ulcers in patients taking rofecoxib or ibuprofen in two randomized controlled trials.	2001 Oct	11563999
Acute, anuric renal failure associated with two doses of a cyclooxygenase-2 inhibitor.	2001 Oct	11549912
Tolerability to new COX-2 inhibitors in NSAID-sensitive patients with cutaneous reactions.	2001 Sep	11570615
Tolerability of rofecoxib.	2001 Sep	11551261
Nephrotoxicity of selective COX-2 inhibitors.	2001 Sep	11550988
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
Arthritis: what it is, why you get it and how to stop the pain.	2001 Sep 3	11550612
Pain relief at a price. A blow to the heart?	2001 Sep 3	11550395
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 `Sat Dec 16 16:31:46 GMT 2023` Edited by `admin` on `Sat Dec 16 16:31:46 GMT 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