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
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
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 |
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 Later on Merck voluntarily withdrawn Vioxx from the market due to safety concerns (high risk of heart attack and stroke).
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL230 |
0.02 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Palliative | VIOXX Approved UseFor 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 Date1999 |
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Palliative | VIOXX Approved UseFor 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 Date1999 |
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Primary | VIOXX Approved UseFor 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 Date1999 |
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Primary | VIOXX Approved UseFor 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 Date1999 |
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Primary | VIOXX Approved UseFor 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 Date1999 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
321 ng/mL |
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 |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17 h |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13% |
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 Sources: |
unhealthy, 44-76 years Health Status: unhealthy Age Group: 44-76 years Sex: M+F Sources: |
Disc. AE: Renal impairment... AEs leading to discontinuation/dose reduction: Renal impairment (grade 1, 1 patient) Sources: |
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 Sources: |
unhealthy, 44-76 years Health Status: unhealthy Age Group: 44-76 years Sex: M+F Sources: |
|
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: |
unhealthy, 58–71years Health Status: unhealthy Age Group: 58–71years Sex: M+F Sources: |
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: |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, 66.8 years Health Status: unhealthy Age Group: 66.8 years Sex: M+F Sources: |
Disc. AE: Dyspepsia, Nausea... AEs leading to discontinuation/dose reduction: Dyspepsia (4.4%) Sources: Nausea (2.4%) Dizziness (2.1%) |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult |
Disc. AE: Death... Other AEs: Hemorrhage, Edema... AEs leading to discontinuation/dose reduction: Death (grade 5, 1653 patients) Other AEs:Hemorrhage (3915 patients) Sources: Edema (3677 patients) Thrombosis (1917 patients) Embolism (233 patients) |
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 Sources: |
unhealthy, 44-76 years Health Status: unhealthy Age Group: 44-76 years Sex: M+F Sources: |
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: |
unhealthy, 58–71years Health Status: unhealthy Age Group: 58–71years Sex: M+F Sources: |
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: |
unhealthy, 58–71years Health Status: unhealthy Age Group: 58–71years Sex: M+F Sources: |
Dizziness | 2.1% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, 66.8 years Health Status: unhealthy Age Group: 66.8 years Sex: M+F Sources: |
Nausea | 2.4% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, 66.8 years Health Status: unhealthy Age Group: 66.8 years Sex: M+F Sources: |
Dyspepsia | 4.4% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, 66.8 years Health Status: unhealthy Age Group: 66.8 years Sex: M+F Sources: |
Thrombosis | 1917 patients | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult |
Embolism | 233 patients | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult |
Edema | 3677 patients | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult |
Hemorrhage | 3915 patients | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult |
Death | grade 5, 1653 patients Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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 Page: 4.0 |
||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
yes [IC50 1.17 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
Page: 4.0 |
weak | |||
Page: 4.0 |
weak | |||
Page: 4.0 |
weak | |||
Page: 4.0 |
weak | |||
Page: 4.0 |
weak | |||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions. | 1999 Nov 26 |
|
Rofecoxib. | 2000 Jul |
|
Alzheimer's disease, inflammation and non-steroidal anti-inflammatory drugs. | 2001 |
|
Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis. | 2001 |
|
Tolerability profiles of rofecoxib (Vioxx) and Arthrotec. A comparison of six weeks treatment in patients with osteoarthritis. | 2001 |
|
A multicenter, randomized, controlled trial to evaluate the safety profile, tolerability, and efficacy of rofecoxib in advanced elderly patients with osteoarthritis. | 2001 Apr |
|
Gastrointestinal damage induced by celecoxib and rofecoxib in rats. | 2001 Apr |
|
Selective COX-2 inhibitors. | 2001 Apr |
|
Cyclo-oxygenase and lipoxygenase pathways in mast cell dependent-neurogenic inflammation induced by electrical stimulation of the rat saphenous nerve. | 2001 Apr |
|
Effects of specific inhibition of cyclo-oxygenase-1 and cyclo-oxygenase-2 in the rat stomach with normal mucosa and after acid challenge. | 2001 Apr |
|
COX-2 inhibitors and the gastrointestinal tract. | 2001 Apr |
|
Rofecoxib (Vioxx): a year in review. | 2001 Apr 3 |
|
Rofecoxib as an alternative in aspirin hypersensitivity. | 2001 Aug |
|
Effects of COX-2 inhibitors on aortic prostacyclin production in cholesterol-fed rabbits. | 2001 Aug |
|
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. | 2001 Feb |
|
FDA refuses companies' request to drop ulcer warning. | 2001 Feb 17 |
|
Efficacy of cyclooxygenase-2-specific inhibitors. | 2001 Feb 19 |
|
Anti-inflammatory drugs, cyclooxygenases and other factors. | 2001 Jan |
|
Effect of rofecoxib on the pharmacokinetics of digoxin in healthy volunteers. | 2001 Jan |
|
Cyclooxygenase inhibitors: any reservations? | 2001 Jan-Feb |
|
Renal effects of COX-2-selective inhibitors. | 2001 Jan-Feb |
|
Gastric preconditioning induced by short ischemia: the role of prostaglandins, nitric oxide and adenosine. | 2001 Jul-Aug |
|
[Selective COX-2 inhibitor. Stomach protection--but not always]. | 2001 Jun 21 |
|
Cyclooxygenase-2 inhibition and renal function. | 2001 Jun 5 |
|
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 |
|
Osteoarthritis management: the role of cyclooxygenase-2-selective inhibitors. | 2001 Mar |
|
[Therapy with preferential and specific COX-2 inhibitors]. | 2001 Mar |
|
Is rofecoxib safer than naproxen? | 2001 Mar |
|
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 |
|
[Cyclooxygenase inhibitors]. | 2001 Mar 17 |
|
Cyclooxygenase-2--specific inhibitors and cardiorenal function: a randomized, controlled trial of celecoxib and rofecoxib in older hypertensive osteoarthritis patients. | 2001 Mar-Apr |
|
Cardiovascular and renal effects of COX-2-specific inhibitors: recent insights and evolving clinical implications. | 2001 Mar-Apr |
|
Current concepts regarding pharmacologic treatment of rheumatoid and osteoarthritis. | 2001 May |
|
Upper gastrointestinal toxicity of rofecoxib and naproxen. | 2001 May 3 |
|
[The coxibs, third generation of non-steroidal anti-inflammatory agents]. | 2001 May-Jun |
|
LC determination of rofecoxib in bulk and pharmaceutical formulations. | 2001 Nov |
|
COX-1 and COX-2 inhibitors. | 2001 Oct |
|
Tolerability to new COX-2 inhibitors in NSAID-sensitive patients with cutaneous reactions. | 2001 Sep |
|
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves. | 2001 Sep 21 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27940550
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
Edited
Wed Apr 02 07:55:36 GMT 2025
by
admin
on
Wed Apr 02 07:55:36 GMT 2025
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Record UNII |
0QTW8Z7MCR
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QM01AH02
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NCI_THESAURUS |
C80509
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CFR |
21 CFR 216.24
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FDA ORPHAN DRUG |
181703
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LIVERTOX |
NBK548628
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WHO-ATC |
M01AH02
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FDA ORPHAN DRUG |
601917
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DB00533
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SUB04261MIG
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C1832
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720256
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ROFECOXIB
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m9647
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100000091590
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162011-90-7
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CHEMBL122
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7262
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758705
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C116926
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232158
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR |
IC50
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METABOLIC ENZYME -> INHIBITOR |
IC50
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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