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 Later on Merck voluntarily withdrawn Vioxx from the market due to safety concerns (high risk of heart attack and stroke).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 Date9.2715837E11 |
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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 Date9.2715837E11 |
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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 Date9.2715837E11 |
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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 Date9.2715837E11 |
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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 Date9.2715837E11 |
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 Co-administed with:: Gefitinib(250 mg) Sources: |
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: |
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 Co-administed with:: Gefitinib(250 mg) Sources: |
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: |
|
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 n = 1167 Health Status: unhealthy Condition: colorectal cancer Age Group: 58–71years Sex: M+F Population Size: 1167 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 (max) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
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: |
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 (typical) Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: |
unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: |
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 Co-administed with:: Gefitinib(250 mg) Sources: |
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: |
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 n = 1167 Health Status: unhealthy Condition: colorectal cancer Age Group: 58–71years Sex: M+F Population Size: 1167 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 n = 1167 Health Status: unhealthy Condition: colorectal cancer Age Group: 58–71years Sex: M+F Population Size: 1167 Sources: |
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: |
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: |
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: |
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: |
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: |
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: |
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: |
unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: |
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: |
unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: |
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: |
unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: |
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: |
unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: |
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: |
unhealthy, adult n = 2200000 Health Status: unhealthy Condition: various Age Group: adult Sex: M+F Population Size: 2200000 Sources: |
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 |
---|---|---|
Effect of local application of growth factors on gastric ulcer healing and mucosal expression of cyclooxygenase-1 and -2. | 2001 |
|
[Selective cyclooxygenase 2 inhibitors (COX-2)]. | 2001 |
|
Potential adverse effects of cyclooxygenase-2 inhibition: evidence from animal models of inflammation. | 2001 |
|
Apoptosis signaling pathways mediated by cyclooxygenase-2 inhibitors in prostate cancer cells. | 2001 |
|
A multicenter, randomized, controlled trial to evaluate the safety profile, tolerability, and efficacy of rofecoxib in advanced elderly patients with osteoarthritis. | 2001 Apr |
|
[The coxibs, third generation anti-inflammatories]. | 2001 Apr |
|
Gastrointestinal damage induced by celecoxib and rofecoxib in rats. | 2001 Apr |
|
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. | 2001 Apr |
|
Cyclo-oxygenase and lipoxygenase pathways in mast cell dependent-neurogenic inflammation induced by electrical stimulation of the rat saphenous nerve. | 2001 Apr |
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Effects of COX-2 inhibitors on aortic prostacyclin production in cholesterol-fed rabbits. | 2001 Aug |
|
Selective and rapid liquid chromatography-mass spectrometry method for the quantification of rofecoxib in pharmacokinetic studies with humans. | 2001 Aug 25 |
|
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 |
|
Safety of a specific COX-2 inhibitor in aspirin-induced asthma. | 2001 Feb |
|
The selective cyclooxygenase-2 inhibitor rofecoxib reduces kainate-induced cell death in the rat hippocampus. | 2001 Feb |
|
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 single-dose and multidose rofecoxib in the treatment of post-orthopedic surgery pain. | 2001 Jan |
|
Effect of rofecoxib on the pharmacokinetics of digoxin in healthy volunteers. | 2001 Jan |
|
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans. | 2001 Jan |
|
[Stomach-saving "Coxibs". No reason for therapeutic risks]. | 2001 Jan 18 |
|
Renal effects of COX-2-selective inhibitors. | 2001 Jan-Feb |
|
Economic evaluation of rofecoxib versus nonselective nonsteroidal anti-inflammatory drugs for the treatment of osteoarthritis. | 2001 Jul |
|
Cyclooxygenase (COX-2) selective inhibitors. Any better than NSAIDs? | 2001 Jul |
|
Induction of delayed follicular rupture in the human by the selective COX-2 inhibitor rofecoxib: a randomized double-blind study. | 2001 Jul |
|
[Safety of specific cyclo-oxygenase 2 inhibitors]. | 2001 Jul 28 |
|
Rofecoxib-induced renal dysfunction in a patient with compensated cirrhosis and heart failure. | 2001 Jun |
|
Cyclooxygenase-1 vs. cyclooxygenase-2 inhibitors in the induction of antinociception in rodent withdrawal reflexes. | 2001 Jun |
|
Classic NSAID and selective cyclooxygenase (COX)-1 and COX-2 inhibitors in healing of chronic gastric ulcers. | 2001 Jun 1 |
|
[Selective COX-2 inhibitor. Stomach protection--but not always]. | 2001 Jun 21 |
|
Cyclooxygenase-2 inhibition and renal function. | 2001 Jun 5 |
|
[Results of the VIGOR study. Rofecoxib halves the complication rate]. | 2001 Jun 7 |
|
[Therapy of arthrosis. Life threatening gastrointestinal events can be reduced]. | 2001 Jun 7 |
|
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 |
|
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-2--specific inhibitors and cardiorenal function: a randomized, controlled trial of celecoxib and rofecoxib in older hypertensive osteoarthritis patients. | 2001 Mar-Apr |
|
[The selective Cox-2 inhibition by rofecoxib reduces risk of severe gastrointestinal complications of anti-inflammatory therapy by more than 50%]. | 2001 May |
|
EULAR recommendations for the management of knee osteoarthritis. | 2001 May |
|
[Clinical use of COX-2 inhibitors]. | 2001 May-Jun |
|
COX-1 and COX-2 inhibitors. | 2001 Oct |
|
Tolerability to new COX-2 inhibitors in NSAID-sensitive patients with cutaneous reactions. | 2001 Sep |
|
Tolerability of rofecoxib. | 2001 Sep |
|
Ischemic preconditioning, the most effective gastroprotective intervention: involvement of prostaglandins, nitric oxide, adenosine and sensory nerves. | 2001 Sep 21 |
|
How safe are your prescription pills? | 2001 Sep 3 |
|
Celecoxib- and rofecoxib-induced delirium. | 2001 Spring |
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
Thu Jul 06 22:00:26 UTC 2023
by
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on
Thu Jul 06 22:00:26 UTC 2023
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Record UNII |
0QTW8Z7MCR
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Record Status |
Validated (UNII)
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WHO-VATC |
QM01AH02
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NCI_THESAURUS |
C80509
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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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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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