etoricoxib ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
selective cyclo-oxygenase inhibitors 1113 202409-33-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • etoricoxib
  • arcoxia
  • etobrix
  • etocox
  • etoxib
  • etropain
  • nucoxia
  • torcoxia
  • MK-0663
A sulfone and pyridine derivative that acts as a cyclooxygenase-2 inhibitor. It is used as a NSAID for the treatment of pain associated with RHEUMATOID ARTHRITIS and ANKYLOSING SPONDYLITIS. It is also used for the short-term treatment of moderate postoperative dental pain.
  • Molecular weight: 358.84
  • Formula: C18H15ClN2O2S
  • CLOGP: 2.35
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 59.92
  • ALOGS: -5.04
  • ROTB: 3

Drug dosage:

DoseUnitRoute
60 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.14 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.78 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.79 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.08 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 26 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1998 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Labelled drug-drug interaction medication error 61.49 16.39 31 7825 13368 63467798
Fixed eruption 41.23 16.39 12 7844 1152 63480014
Apraxia 39.95 16.39 13 7843 1808 63479358
Perseveration 35.72 16.39 8 7848 267 63480899
Disorientation 35.00 16.39 33 7823 39419 63441747
Inflammatory marker increased 34.87 16.39 17 7839 6822 63474344
Spinal pain 34.38 16.39 21 7835 13118 63468048
Chronic gastritis 34.30 16.39 13 7843 2828 63478338
Porphyrins urine increased 31.38 16.39 5 7851 23 63481143
Acquired porphyria 31.38 16.39 5 7851 23 63481143
Thrombocytosis 31.28 16.39 15 7841 5803 63475363
Porphyrins stool increased 30.26 16.39 5 7851 30 63481136
Drug abuse 28.82 16.39 40 7816 72478 63408688
Joint contracture 28.70 16.39 10 7846 1714 63479452
Lumbar vertebral fracture 28.30 16.39 14 7842 5796 63475370
Axial spondyloarthritis 28.00 16.39 7 7849 377 63480789
Synovectomy 27.28 16.39 6 7850 184 63480982
Meteoropathy 26.45 16.39 4 7852 12 63481154
Spinal osteoarthritis 25.77 16.39 19 7837 16167 63464999
Thoracic vertebral fracture 25.18 16.39 12 7844 4580 63476586
Postoperative delirium 25.17 16.39 5 7851 92 63481074
Porphyria non-acute 24.61 16.39 6 7850 291 63480875
Drug interaction 24.52 16.39 73 7783 229058 63252108
Polymyalgia rheumatica 24.18 16.39 11 7845 3780 63477386
Ovulation disorder 23.55 16.39 4 7852 29 63481137
Synovial disorder 23.40 16.39 9 7847 2036 63479130
Serum ferritin decreased 23.29 16.39 9 7847 2061 63479105
Ankylosing spondylitis 23.04 16.39 15 7841 10459 63470707
Sopor 22.50 16.39 20 7836 22144 63459022
Aortic valve stenosis 22.40 16.39 10 7846 3289 63477877
Spinal fracture 21.62 16.39 18 7838 18253 63462913
Femur fracture 21.21 16.39 26 7830 41730 63439436
Hemianopia 20.68 16.39 7 7849 1100 63480066
Infusion related reaction 20.48 16.39 3 7853 245518 63235648
Withdrawal syndrome 20.21 16.39 18 7838 19979 63461187
Hepatitis A antibody abnormal 20.02 16.39 4 7852 76 63481090
Interspinous osteoarthritis 20.02 16.39 4 7852 76 63481090
Pyelocaliectasis 19.95 16.39 6 7850 645 63480521
Urticaria 19.83 16.39 55 7801 165747 63315419
Product prescribing error 19.59 16.39 20 7836 26269 63454897
Subileus 19.57 16.39 9 7847 3170 63477996
Hyperreflexia 19.52 16.39 11 7845 5923 63475243
Hallucination, visual 18.77 16.39 17 7839 19281 63461885
Allodynia 18.59 16.39 6 7850 813 63480353
Toxic epidermal necrolysis 18.39 16.39 19 7837 25315 63455851
Renal function test abnormal 18.38 16.39 9 7847 3644 63477522
Junctional ectopic tachycardia 18.37 16.39 4 7852 117 63481049
Sudden death 18.31 16.39 13 7843 10436 63470730
Drug eruption 18.14 16.39 20 7836 28674 63452492
Carotid artery stenosis 18.14 16.39 10 7846 5160 63476006
Lactic acidosis 18.10 16.39 23 7833 38264 63442902
Alopecia 17.54 16.39 10 7846 337526 63143640
Osteoarthritis 17.13 16.39 37 7819 95306 63385860
Ulnar nerve injury 17.11 16.39 4 7852 162 63481004
Speech disorder 17.02 16.39 23 7833 40606 63440560
Angioedema 16.91 16.39 25 7831 47940 63433226
Spondylitis 16.89 16.39 9 7847 4345 63476821

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Regurgitation 78.41 17.84 23 5818 1676 34949414
General physical health deterioration 65.37 17.84 93 5748 128176 34822914
Oropharyngeal discomfort 64.12 17.84 23 5818 3173 34947917
Vitamin B12 deficiency 62.48 17.84 24 5817 4007 34947083
Eructation 55.36 17.84 23 5818 4708 34946382
Spinal pain 53.69 17.84 24 5817 5865 34945225
Systemic infection 49.95 17.84 22 5819 5190 34945900
Hepatitis E antibody positive 49.64 17.84 11 5830 256 34950834
Body mass index abnormal 49.09 17.84 10 5831 153 34950937
Hepatitis E virus test positive 48.40 17.84 11 5830 288 34950802
Oral mucosa erosion 44.15 17.84 13 5828 959 34950131
Mucosal necrosis 43.58 17.84 8 5833 68 34951022
Neck pain 43.23 17.84 35 5806 25314 34925776
Antiphospholipid antibodies positive 42.37 17.84 10 5831 310 34950780
Death 41.86 17.84 8 5833 398041 34553049
Ligament calcification 40.55 17.84 9 5832 211 34950879
Product prescribing error 39.82 17.84 32 5809 22895 34928195
Palmoplantar pustulosis 39.61 17.84 8 5833 117 34950973
Suspected transmission of an infectious agent via product 37.02 17.84 11 5830 837 34950253
Coating in mouth 35.94 17.84 7 5834 84 34951006
Lip erosion 35.56 17.84 10 5831 626 34950464
Respiratory fatigue 34.88 17.84 7 5834 99 34950991
Hand fracture 33.78 17.84 13 5828 2179 34948911
Pregnancy of partner 31.50 17.84 8 5833 338 34950752
Sacroiliitis 30.87 17.84 11 5830 1487 34949603
Helicobacter gastritis 29.01 17.84 10 5831 1226 34949864
Craniocerebral injury 28.79 17.84 13 5828 3250 34947840
Adjustment disorder with disturbance of conduct 28.08 17.84 6 5835 117 34950973
Fluid intake reduced 27.22 17.84 13 5828 3688 34947402
Otitis media 27.12 17.84 12 5829 2860 34948230
Ankylosing spondylitis 24.82 17.84 14 5827 5590 34945500
Gastrointestinal inflammation 24.82 17.84 12 5829 3499 34947591
Costovertebral angle tenderness 23.48 17.84 5 5836 96 34950994
Poor peripheral circulation 23.45 17.84 9 5832 1498 34949592
Chronic idiopathic pain syndrome 23.31 17.84 4 5837 22 34951068
Immune-mediated adverse reaction 23.06 17.84 7 5834 573 34950517
Oral pruritus 22.42 17.84 6 5835 312 34950778
Formication 22.30 17.84 9 5832 1710 34949380
Peritoneal adhesions 21.89 17.84 5 5836 134 34950956
Axial spondyloarthritis 21.81 17.84 6 5835 346 34950744
Prerenal failure 20.62 17.84 9 5832 2075 34949015
Personality change 20.52 17.84 12 5829 5127 34945963
Mucosal ulceration 19.35 17.84 7 5834 988 34950102
Intensive care unit acquired weakness 19.14 17.84 7 5834 1020 34950070
Hypercholesterolaemia 19.09 17.84 14 5827 8748 34942342
Arthralgia 19.02 17.84 67 5774 169974 34781116
pH body fluid increased 18.97 17.84 4 5837 73 34951017
Sialadenosis 18.94 17.84 3 5838 9 34951081
Cardiac valve sclerosis 18.63 17.84 4 5837 80 34951010
Polyneuropathy 18.17 17.84 17 5824 14879 34936211
Endocarditis 17.91 17.84 12 5829 6499 34944591
Toxic epidermal necrolysis 17.84 17.84 20 5821 21626 34929464

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Regurgitation 64.81 14.79 22 12404 2765 79729197
General physical health deterioration 60.74 14.79 133 12293 275105 79456857
Product prescribing error 59.47 14.79 52 12374 44761 79687201
Spinal pain 58.59 14.79 34 12392 15358 79716604
Oral mucosa erosion 51.76 14.79 17 12409 1930 79730032
Hepatitis E antibody positive 50.36 14.79 11 12415 257 79731705
Hepatitis E virus test positive 49.23 14.79 11 12415 286 79731676
Labelled drug-drug interaction medication error 46.91 14.79 37 12389 27613 79704349
Body mass index abnormal 45.52 14.79 10 12416 240 79731722
Oropharyngeal discomfort 44.71 14.79 22 12404 7144 79724818
Vitamin B12 deficiency 44.49 14.79 22 12404 7219 79724743
Ligament calcification 41.13 14.79 9 12417 212 79731750
Perseveration 40.92 14.79 10 12416 387 79731575
Mucosal necrosis 39.79 14.79 8 12418 123 79731839
Lip erosion 38.98 14.79 13 12413 1547 79730415
Ankylosing spondylitis 38.77 14.79 24 12402 12181 79719781
Systemic infection 38.33 14.79 22 12404 9730 79722232
Fixed eruption 37.73 14.79 15 12411 2939 79729023
Immune-mediated adverse reaction 37.20 14.79 11 12415 883 79731079
Axial spondyloarthritis 37.06 14.79 10 12416 576 79731386
Inflammatory marker increased 36.36 14.79 22 12404 10718 79721244
Eructation 36.05 14.79 22 12404 10887 79721075
Toxic epidermal necrolysis 35.27 14.79 39 12387 44542 79687420
Suspected transmission of an infectious agent via product 34.14 14.79 11 12415 1175 79730787
Coating in mouth 33.80 14.79 8 12418 270 79731692
Thrombocytosis 32.89 14.79 19 12407 8507 79723455
Death 31.90 14.79 25 12401 566489 79165473
Polymyalgia rheumatica 31.54 14.79 15 12411 4522 79727440
Femur fracture 30.90 14.79 34 12392 38618 79693344
Lumbar vertebral fracture 30.74 14.79 17 12409 7005 79724957
Antiphospholipid antibodies positive 30.01 14.79 9 12417 759 79731203
Chronic gastritis 29.97 14.79 14 12412 4054 79727908
Thoracic vertebral fracture 29.45 14.79 15 12411 5238 79726724
Synovectomy 29.41 14.79 7 12419 242 79731720
Porphyrins urine increased 29.26 14.79 5 12421 29 79731933
Pregnancy of partner 28.97 14.79 7 12419 258 79731704
Respiratory fatigue 28.84 14.79 7 12419 263 79731699
Drug interaction 28.46 14.79 134 12292 415049 79316913
Acquired porphyria 28.20 14.79 5 12421 37 79731925
Apraxia 27.94 14.79 12 12414 2855 79729107
Palmoplantar pustulosis 27.92 14.79 8 12418 575 79731387
Sacroiliitis 27.91 14.79 13 12413 3741 79728221
Skin hyperpigmentation 27.44 14.79 16 12410 7287 79724675
Porphyrins stool increased 27.43 14.79 5 12421 44 79731918
Helicobacter gastritis 26.36 14.79 11 12415 2438 79729524
Neck pain 25.88 14.79 44 12382 75373 79656589
Meteoropathy 25.53 14.79 4 12422 12 79731950
Sopor 24.61 14.79 28 12398 32982 79698980
Craniocerebral injury 23.91 14.79 13 12413 5183 79726779
Disorientation 23.38 14.79 38 12388 62738 79669224
Completed suicide 23.16 14.79 5 12421 245762 79486200
Joint contracture 22.76 14.79 10 12416 2514 79729448
Poor peripheral circulation 22.06 14.79 11 12415 3672 79728290
Toxicity to various agents 21.99 14.79 20 12406 421520 79310442
Haemophilic arthropathy 21.99 14.79 5 12421 141 79731821
Chronic idiopathic pain syndrome 21.86 14.79 4 12422 36 79731926
Synovial disorder 21.66 14.79 9 12417 1974 79729988
Fluid intake reduced 21.60 14.79 13 12413 6275 79725687
Infusion related reaction 21.06 14.79 5 12421 230232 79501730
Tongue oedema 20.11 14.79 13 12413 7104 79724858
Urticaria 20.07 14.79 69 12357 185132 79546830
Musculoskeletal pain 19.78 14.79 47 12379 102307 79629655
Hemianopia 19.40 14.79 8 12418 1720 79730242
Otitis media 19.37 14.79 12 12414 6094 79725868
Costovertebral angle tenderness 19.33 14.79 5 12421 244 79731718
Dysuria 19.19 14.79 31 12395 50920 79681042
Hand fracture 19.16 14.79 12 12414 6213 79725749
Hepatitis A antibody abnormal 19.10 14.79 4 12422 76 79731886
Interspinous osteoarthritis 19.10 14.79 4 12422 76 79731886
pH body fluid increased 18.95 14.79 4 12422 79 79731883
Renal function test abnormal 18.91 14.79 11 12415 4987 79726975
Weight increased 18.63 14.79 10 12416 277376 79454586
Aortic valve stenosis 18.32 14.79 11 12415 5283 79726679
Spinal fracture 18.23 14.79 18 12408 18036 79713926
Hyperreflexia 18.18 14.79 13 12413 8372 79723590
Porphyria non-acute 17.76 14.79 6 12420 743 79731219
Spondylolisthesis 17.61 14.79 9 12417 3166 79728796
Cardiac valve sclerosis 17.58 14.79 4 12422 113 79731849
Peritoneal adhesions 17.58 14.79 5 12421 350 79731612
Postoperative delirium 17.47 14.79 5 12421 358 79731604
Spinal osteoarthritis 17.32 14.79 17 12409 16910 79715052
Gastrointestinal submucosal tumour 17.13 14.79 4 12422 127 79731835
Gastrointestinal inflammation 17.06 14.79 12 12414 7532 79724430
Drug eruption 16.91 14.79 27 12399 43908 79688054
Disease progression 16.87 14.79 4 12422 184358 79547604
Spondylitis 16.82 14.79 10 12416 4721 79727241
Prerenal failure 16.32 14.79 9 12417 3689 79728273
Iridocyclitis 16.30 14.79 9 12417 3695 79728267
Gamma-glutamyltransferase increased 16.30 14.79 30 12396 54650 79677312
Ulnar nerve injury 16.17 14.79 4 12422 163 79731799
Mucosal ulceration 15.54 14.79 7 12419 1866 79730096
Withdrawal syndrome 15.48 14.79 20 12406 26834 79705128
Urethral stenosis 15.47 14.79 6 12420 1100 79730862
Lactic acidosis 15.47 14.79 34 12392 70325 79661637
Off label use 15.40 14.79 81 12345 907134 78824828
Psychotic behaviour 15.35 14.79 6 12420 1123 79730839
Intensive care unit acquired weakness 15.32 14.79 7 12419 1926 79730036
Psoriatic arthropathy 15.27 14.79 36 12390 77963 79653999
Subileus 15.18 14.79 10 12416 5644 79726318

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AH05 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Coxibs
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D052246 Cyclooxygenase 2 Inhibitors
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory agent
CHEBI has role CHEBI:50629 COX-2 inhibitor

Drug Use | Suggest Off label Use Form| |View source of the data|

None




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.6 Basic
pKa2 1.75 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 6.10 WOMBAT-PK IUPHAR
Prostaglandin G/H synthase 1 Enzyme IC50 4.92 CHEMBL
Prostaglandin E2 receptor EP2 subtype GPCR Ki 7.10 PDSP
Mitogen-activated protein kinase 14 Kinase IC50 6.28 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.64 CHEMBL

External reference:

IDSource
D03710 KEGG_DRUG
C0972314 UMLSCUI
CHEBI:6339 CHEBI
5CH PDB_CHEM_ID
CHEMBL416146 ChEMBL_ID
DB01628 DRUGBANK_ID
D000077613 MESH_DESCRIPTOR_UI
123619 PUBCHEM_CID
2896 IUPHAR_LIGAND_ID
8082 INN_ID
WRX4NFY03R UNII
307296 RXNORM
009633 NDDF
395292007 SNOMEDCT_US
409134009 SNOMEDCT_US

Pharmaceutical products:

None