Identification

Name
Etoricoxib
Accession Number
DB01628  (DB07166)
Type
Small Molecule
Groups
Approved, Investigational
Description

Etoricoxib is a new COX-2 selective inhibitor. Current therapeutic indications are: treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. Like any other COX-2 selective inhibitor, Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2). This reduces the generation of prostaglandins (PGs) from arachidonic acid.

Structure
Thumb
Synonyms
  • 5-chloro-2-(6-Methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine
  • 5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl
  • 5-chloro-6'-Methyl-3-(P-(methylsulfonyl)phenyl)-2,3'-bipyridine
  • ETORICOXIB
  • Etoricoxibum
  • L791456
External IDs
L-791456 / MK-0663 / MK-663
Product Ingredients
IngredientUNIICASInChI Key
Etoricoxib hydrochloride138Y28RY5E202409-40-3NNGHGPAKTWAHHB-UHFFFAOYSA-N
International/Other Brands
Algix / Arcoxia / Coxyveen (Solmarc Lifesciences) / Etorix / Nucoxia / Tauxib
Categories
UNII
WRX4NFY03R
CAS number
202409-33-4
Weight
Average: 358.842
Monoisotopic: 358.054276131
Chemical Formula
C18H15ClN2O2S
InChI Key
MNJVRJDLRVPLFE-UHFFFAOYSA-N
InChI
InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
IUPAC Name
5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine
SMILES
CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O

Pharmacology

Indication

For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.

Pharmacodynamics

Etoricoxib is a COX-2 selective inhibitor (approximately 106 times more selective for COX-2 inhibition over COX-1). Currently it is approved in more than 60 countries worldwide but not in the US, where the Food and Drug Administration (FDA) require additional safety and efficacy data for etoricoxib before it will issue approval.

Mechanism of action

Like any other COX-2 selective inhibitor Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2). This reduces prostaglandins (PGs) generation from arachidonic acid.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
Absorption

Bioavailability is 100% following oral administration.

Volume of distribution
Not Available
Protein binding

92%

Metabolism

Hepatic, primarily via CYP3A4.

Route of elimination
Not Available
Half life

22 hours

Clearance
Not Available
Toxicity

This reduced activity is the cause of reduced gastrointestinal toxicity, as demonstrated in several large clinical trials performed with different COXIB (see below links on NEJM and The Lancet). Some clinical trials and meta-analysis showed that treatment with COXIB lead to increased incidence of cardiovascular adverse events compared to placebo

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Etoricoxib Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Etoricoxib.
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Etoricoxib.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Etoricoxib.
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Etoricoxib is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Etoricoxib is combined with 19-norandrostenedione.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Etoricoxib.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Etoricoxib.
5-androstenedioneThe risk or severity of adverse effects can be increased when Etoricoxib is combined with 5-androstenedione.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Etoricoxib.
6-Deoxyerythronolide BThe metabolism of Etoricoxib can be decreased when combined with 6-Deoxyerythronolide B.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Andrea Castellin, Paolo Stabile, Francesco Fontana, Ottorino De Lucchi, Andrea Caporale, Stefano Tartaggia, "PROCESS FOR PREPARING 1-(6-METHYLPYRIDIN-3-YL)-2-[4-(METHYLSULFONYL)PHENYL]ETHANONE, AN INTERMEDIATE OF ETORICOXIB." U.S. Patent US20120232281, issued September 13, 2012.

US20120232281
General References
Not Available
External Links
Human Metabolome Database
HMDB0015565
KEGG Drug
D03710
KEGG Compound
C11718
PubChem Compound
123619
PubChem Substance
46504505
ChemSpider
110209
BindingDB
50072064
ChEBI
6339
ChEMBL
CHEMBL416146
Therapeutic Targets Database
DAP000738
PharmGKB
PA164776853
HET
5CH
Wikipedia
Etoricoxib
ATC Codes
M01AH05 — Etoricoxib
PDB Entries
3cfl

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentMuscle pains1
1CompletedTreatmentPain NOS1
1RecruitingTreatmentTuberculosis1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedTreatmentProstate Cancer1
2CompletedTreatmentRheumatoid Arthritis1
2RecruitingTreatmentAnkylosing Spondylitis (AS)1
2TerminatedTreatmentComplex Regional Pain Syndrome Type II / Peripheral Nerve Injury (PNI) / Polyneuropathies / Postherpetic Neuralgia / Radicular syndrome1
2TerminatedTreatmentOsteoarthritis, Hip / Pain NOS / Postoperative pain1
3Active Not RecruitingTreatmentBrachial Plexus Block / Postoperative pain1
3CompletedTreatmentAcute Pain Following a Total Abdominal Hysterectomy1
3CompletedTreatmentAnkylosing Spondylitis (AS)2
3CompletedTreatmentAnterior Cruciate Ligament Injury1
3CompletedTreatmentArthroplasties Hip Replacement / Osteoarthritis, Hip / Perioperative Blood Loss1
3CompletedTreatmentDysmenorrhea2
3CompletedTreatmentHysterectomy / Oophorectomy / Postoperative pain / Tubal Excision1
3CompletedTreatmentKnee Osteoarthritis (Knee OA)1
3CompletedTreatmentOsteoarthritis (OA)4
3CompletedTreatmentPostoperative Dental Pain1
3CompletedTreatmentPostoperative pain3
3CompletedTreatmentRheumatoid Arthritis2
3CompletedTreatmentRheumatoid Arthritis,Osteoarthritis1
3RecruitingTreatmentPrimary Hypertrophic Osteoarthropathy1
3TerminatedTreatmentSoft Tissue Injuries of the Shoulder / Tenosynovitis and Bursitis Affecting the Shoulder1
4Active Not RecruitingNot AvailableAcute Gouty Arthritis / Ankylosing Spondylitis (AS) / Arthritis / Osteoarthritis (OA) / Rheumatoid Arthritis1
4CompletedPreventionFasting / Fasting Headache / Headaches / Ramadan Headache1
4CompletedPreventionOssification, Heterotopic1
4CompletedTreatmentAchilles Tendinopathy1
4CompletedTreatmentCyclooxygenase Two Inhibitors / Etoricoxib / Periodontitis / Saliva / Superoxide Dismutase1
4CompletedTreatmentLaparoscopic Surgery for Appendicitis / Laparoscopic Surgery for Cholecystitis / Laparoscopic Surgery for Ovarian Cysts1
4CompletedTreatmentOsteoarthritis (OA) / Pain NOS1
4CompletedTreatmentPain NOS2
4CompletedTreatmentPost-operational Pain1
4CompletedTreatmentPostoperative pain2
4CompletedTreatmentRupture of Anterior Cruciate Ligament1
4TerminatedPreventionPain NOS1
4TerminatedTreatmentPost-Operative Pain1
4Unknown StatusPreventionHeadaches1
4Unknown StatusTreatmentDental Extraction1
4Unknown StatusTreatmentFibromyalgia1
4Unknown StatusTreatmentLow Back Pain (LBP)1
4Unknown StatusTreatmentPain, Acute1
4Unknown StatusTreatmentNeurocostal neuralgia / Postherpetic Neuralgia1
4Unknown StatusTreatmentRheumatoid Arthritis1
4WithdrawnTreatmentHallux Valgus / Postoperative pain1
4WithdrawnTreatmentOsteoarthritis (OA)1
4WithdrawnTreatmentSprains1
Not AvailableActive Not RecruitingNot AvailableSpondylarthropathies; Spondylitis, Ankylosing1
Not AvailableCompletedNot AvailableAnkylosing Spondylitis (AS)1
Not AvailableCompletedNot AvailableOsteoarthritis (OA)1
Not AvailableCompletedBasic ScienceAsthma Bronchial1
Not AvailableCompletedPreventionColor Changes During Tooth Formation1
Not AvailableCompletedPreventionPostoperative pain1
Not AvailableCompletedTreatmentAdverse Anesthesia Outcome1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1
Not AvailableCompletedTreatmentProliferative Diabetic Retinopathy (PDR)1
Not AvailableRecruitingTreatmentAnaesthesia therapy / Anesthesia Morbidity / Breast Neoplasm Female / Regional Anesthesia / Regional Anesthesia Morbidity1
Not AvailableRecruitingTreatmentCervical Osteoarthritis1
Not AvailableUnknown StatusTreatmentEdema / Pain NOS / Trismus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00328 mg/mLALOGPS
logP3.7ALOGPS
logP2.79ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)19.69ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.92 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.04 m3·mol-1ChemAxon
Polarizability36.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9776
Blood Brain Barrier+0.9399
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.845
P-glycoprotein inhibitor INon-inhibitor0.7624
P-glycoprotein inhibitor IINon-inhibitor0.9869
Renal organic cation transporterNon-inhibitor0.8267
CYP450 2C9 substrateNon-substrate0.6702
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.506
CYP450 1A2 substrateInhibitor0.6415
CYP450 2C9 inhibitorInhibitor0.8528
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorInhibitor0.9087
CYP450 3A4 inhibitorInhibitor0.585
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8848
Ames testNon AMES toxic0.7952
CarcinogenicityNon-carcinogens0.6856
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.4100 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9934
hERG inhibition (predictor II)Non-inhibitor0.8582
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Bipyridines and oligopyridines
Direct Parent
Bipyridines and oligopyridines
Alternative Parents
Phenylpyridines / Benzenesulfonyl compounds / Methylpyridines / Aryl chlorides / Sulfones / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides
show 2 more
Substituents
Bipyridine / 3-phenylpyridine / Benzenesulfonyl group / Methylpyridine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Sulfone / Sulfonyl
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfone, organochlorine compound, bipyridines (CHEBI:6339)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Capone ML, Tacconelli S, Di Francesco L, Sacchetti A, Sciulli MG, Patrignani P: Pharmacodynamic of cyclooxygenase inhibitors in humans. Prostaglandins Other Lipid Mediat. 2007 Jan;82(1-4):85-94. Epub 2006 Jul 3. [PubMed:17164136]
  4. FitzGerald GA: COX-2 in play at the AHA and the FDA. Trends Pharmacol Sci. 2007 Jul;28(7):303-7. Epub 2007 Jun 18. [PubMed:17573128]
  5. Yuan Y, Hunt RH: Global gastrointestinal safety profile of etoricoxib and lumiracoxib. Curr Pharm Des. 2007;13(22):2237-47. [PubMed:17691997]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Takemoto JK, Reynolds JK, Remsberg CM, Vega-Villa KR, Davies NM: Clinical pharmacokinetic and pharmacodynamic profile of etoricoxib. Clin Pharmacokinet. 2008;47(11):703-20. [PubMed:18840026]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
Data based on findings of in vitro studies.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Kassahun K, McIntosh IS, Shou M, Walsh DJ, Rodeheffer C, Slaughter DE, Geer LA, Halpin RA, Agrawal N, Rodrigues AD: Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor. Drug Metab Dispos. 2001 Jun;29(6):813-20. [PubMed:11353749]
  2. Etoricoxib FDA label [File]
  3. EMA Etoricoxib Assessment [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Lin LY, Di Stefano EW, Schmitz DA, Hsu L, Ellis SW, Lennard MS, Tucker GT, Cho AK: Oxidation of methamphetamine and methylenedioxymethamphetamine by CYP2D6. Drug Metab Dispos. 1997 Sep;25(9):1059-64. [PubMed:9311621]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Kassahun K, McIntosh IS, Shou M, Walsh DJ, Rodeheffer C, Slaughter DE, Geer LA, Halpin RA, Agrawal N, Rodrigues AD: Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor. Drug Metab Dispos. 2001 Jun;29(6):813-20. [PubMed:11353749]
  3. Etoricoxib FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Kassahun K, McIntosh IS, Shou M, Walsh DJ, Rodeheffer C, Slaughter DE, Geer LA, Halpin RA, Agrawal N, Rodrigues AD: Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor. Drug Metab Dispos. 2001 Jun;29(6):813-20. [PubMed:11353749]
  3. Medhi B, Sukhija M, Prakash A, Gaikwad S, Bansal V, Pandhi P: Effects of etoricoxib on the pharmacokinetics of phenytoin. Pharmacol Rep. 2008 Mar-Apr;60(2):233-7. [PubMed:18443385]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Kassahun K, McIntosh IS, Shou M, Walsh DJ, Rodeheffer C, Slaughter DE, Geer LA, Halpin RA, Agrawal N, Rodrigues AD: Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor. Drug Metab Dispos. 2001 Jun;29(6):813-20. [PubMed:11353749]

Drug created on August 30, 2007 09:49 / Updated on October 21, 2018 20:32