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 53.42 16.34 27 7028 11559 56273453
Fixed eruption 43.57 16.34 12 7043 931 56284081
Apraxia 40.53 16.34 13 7042 1706 56283306
Drug abuse 38.71 16.34 45 7010 67565 56217447
Disorientation 36.75 16.34 33 7022 36580 56248432
Inflammatory marker increased 36.54 16.34 17 7038 6073 56278939
Spinal pain 36.09 16.34 21 7034 11863 56273149
Perseveration 35.97 16.34 8 7047 255 56284757
Chronic gastritis 35.37 16.34 13 7042 2565 56282447
Axial spondyloarthritis 35.33 16.34 8 7047 277 56284735
Thrombocytosis 32.27 16.34 15 7040 5347 56279665
Acquired porphyria 31.31 16.34 5 7050 23 56284989
Porphyrins urine increased 31.31 16.34 5 7050 23 56284989
Lumbar vertebral fracture 30.23 16.34 14 7041 4950 56280062
Porphyrins stool increased 30.20 16.34 5 7050 30 56284982
Joint contracture 28.70 16.34 10 7045 1692 56283320
Synovial disorder 28.57 16.34 9 7046 1114 56283898
Synovectomy 27.56 16.34 6 7049 173 56284839
Meteoropathy 26.40 16.34 4 7051 12 56285000
Polymyalgia rheumatica 26.24 16.34 11 7044 3071 56281941
Drug interaction 25.97 16.34 71 6984 209684 56075328
Thoracic vertebral fracture 25.89 16.34 12 7043 4251 56280761
Postoperative delirium 25.43 16.34 5 7050 86 56284926
Porphyria non-acute 24.50 16.34 6 7049 293 56284719
Serum ferritin decreased 24.27 16.34 9 7046 1819 56283193
Ovulation disorder 24.02 16.34 4 7051 25 56284987
Spinal fracture 23.11 16.34 18 7037 16406 56268606
Aortic valve stenosis 22.73 16.34 10 7045 3137 56281875
Femur fracture 22.22 16.34 26 7029 39269 56245743
Withdrawal syndrome 21.26 16.34 18 7037 18444 56266568
Ankylosing spondylitis 21.14 16.34 14 7041 9916 56275096
Hemianopia 20.98 16.34 7 7048 1039 56283973
Abdominal pain upper 20.72 16.34 59 6996 178254 56106758
Intervertebral disc protrusion 20.68 16.34 19 7036 21675 56263337
Hyperreflexia 20.65 16.34 11 7044 5239 56279773
Subileus 20.12 16.34 9 7046 2935 56282077
Renal function test abnormal 20.04 16.34 9 7046 2962 56282050
Product prescribing error 19.60 16.34 19 7036 23167 56261845
Urticaria 18.92 16.34 50 7005 144626 56140386
Allodynia 18.72 16.34 6 7049 785 56284227
Carotid artery stenosis 18.50 16.34 10 7045 4900 56280112
Junctional ectopic tachycardia 18.45 16.34 4 7051 113 56284899
Angioedema 17.95 16.34 24 7031 41429 56243583
Sopor 17.41 16.34 17 7038 20905 56264107
Infected fistula 17.18 16.34 4 7051 157 56284855
Groin pain 17.11 16.34 12 7043 9328 56275684
Red blood cell sedimentation rate increased 17.09 16.34 22 7033 36601 56248411
Infusion related reaction 16.72 16.34 3 7052 208928 56076084
Speech disorder 16.68 16.34 22 7033 37471 56247541
Alopecia 16.63 16.34 8 7047 293450 55991562
Substance abuse 16.45 16.34 9 7046 4516 56280496

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 74.55 19.57 21 5261 1328 31690734
Oropharyngeal discomfort 59.96 19.57 21 5261 2710 31689352
Vitamin B12 deficiency 58.38 19.57 22 5260 3497 31688565
Spinal pain 53.35 19.57 23 5259 5172 31686890
Eructation 51.27 19.57 21 5261 4158 31687904
Hepatitis E antibody positive 49.67 19.57 11 5271 256 31691806
Body mass index abnormal 49.62 19.57 10 5272 145 31691917
Hepatitis E virus test positive 48.58 19.57 11 5271 284 31691778
Oral mucosa erosion 45.51 19.57 13 5269 864 31691198
Mucosal necrosis 44.26 19.57 8 5274 62 31692000
Antiphospholipid antibodies positive 43.04 19.57 10 5272 290 31691772
Neck pain 42.08 19.57 33 5249 22877 31669185
Ligament calcification 40.57 19.57 9 5273 211 31691851
Palmoplantar pustulosis 39.76 19.57 8 5274 115 31691947
General physical health deterioration 38.19 19.57 68 5214 113367 31578695
Suspected transmission of an infectious agent via product 37.69 19.57 11 5271 789 31691273
Lip erosion 37.23 19.57 10 5272 529 31691533
Hand fracture 36.59 19.57 13 5269 1748 31690314
Coating in mouth 36.52 19.57 7 5275 77 31691985
Death 36.21 19.57 8 5274 360561 31331501
Ankylosing spondylitis 35.40 19.57 18 5264 5863 31686199
Respiratory fatigue 34.96 19.57 7 5275 98 31691964
Product prescribing error 33.30 19.57 27 5255 19615 31672447
Sacroiliitis 31.96 19.57 11 5271 1347 31690715
Craniocerebral injury 30.51 19.57 13 5269 2837 31689225
Helicobacter gastritis 29.25 19.57 10 5272 1200 31690862
Otitis media 28.23 19.57 12 5270 2604 31689458
Systemic infection 28.13 19.57 13 5269 3436 31688626
Pregnancy of partner 27.09 19.57 7 5275 318 31691744
Psoriatic arthropathy 26.88 19.57 24 5258 19859 31672203
Gastrointestinal inflammation 25.82 19.57 12 5270 3213 31688849
Chronic idiopathic pain syndrome 24.37 19.57 4 5278 16 31692046
Immune-mediated adverse reaction 24.15 19.57 7 5275 490 31691572
Poor peripheral circulation 23.95 19.57 9 5273 1418 31690644
Costovertebral angle tenderness 23.64 19.57 5 5277 93 31691969
Oral pruritus 23.15 19.57 6 5276 276 31691786
Formication 23.02 19.57 9 5273 1578 31690484
Peritoneal adhesions 22.01 19.57 5 5277 131 31691931
Prerenal failure 21.67 19.57 9 5273 1844 31690218
Axial spondyloarthritis 21.66 19.57 6 5276 356 31691706
Personality change 21.32 19.57 12 5270 4783 31687279
Hypercholesterolaemia 20.22 19.57 14 5268 8016 31684046
Polyneuropathy 20.19 19.57 17 5265 13005 31679057
Mucosal ulceration 19.77 19.57 7 5275 931 31691131
Intensive care unit acquired weakness 19.60 19.57 7 5275 955 31691107
Toxic epidermal necrolysis 19.60 19.57 20 5262 19504 31672558

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
Spinal pain 58.91 14.87 33 11187 13737 70903487
Regurgitation 56.89 14.87 19 11201 2237 70914987
Oral mucosa erosion 53.15 14.87 17 11203 1748 70915476
Product prescribing error 52.71 14.87 46 11174 38906 70878318
Hepatitis E antibody positive 50.19 14.87 11 11209 257 70916967
Hepatitis E virus test positive 49.29 14.87 11 11209 280 70916944
Body mass index abnormal 45.78 14.87 10 11210 230 70916994
Ankylosing spondylitis 42.06 14.87 25 11195 11621 70905603
Perseveration 41.15 14.87 10 11210 372 70916852
Ligament calcification 41.00 14.87 9 11211 212 70917012
Lip erosion 40.43 14.87 13 11207 1359 70915865
Mucosal necrosis 40.17 14.87 8 11212 115 70917109
Inflammatory marker increased 39.06 14.87 22 11198 9252 70907972
Vitamin B12 deficiency 38.99 14.87 19 11201 5953 70911271
Oropharyngeal discomfort 38.66 14.87 19 11201 6060 70911164
Immune-mediated adverse reaction 37.89 14.87 11 11209 816 70916408
General physical health deterioration 37.03 14.87 101 11119 235930 70681294
Fixed eruption 36.36 14.87 14 11206 2482 70914742
Suspected transmission of an infectious agent via product 34.70 14.87 11 11209 1098 70916126
Coating in mouth 34.46 14.87 8 11212 244 70916980
Thrombocytosis 34.24 14.87 19 11201 7765 70909459
Labelled drug-drug interaction medication error 33.66 14.87 29 11191 24098 70893126
Polymyalgia rheumatica 33.54 14.87 15 11205 3871 70913353
Lumbar vertebral fracture 33.05 14.87 17 11203 5970 70911254
Antiphospholipid antibodies positive 30.68 14.87 9 11211 692 70916532
Thoracic vertebral fracture 30.48 14.87 15 11205 4799 70912425
Eructation 30.25 14.87 19 11201 9741 70907483
Synovectomy 29.74 14.87 7 11213 227 70916997
Drug interaction 29.57 14.87 129 11091 381312 70535912
Sacroiliitis 29.43 14.87 13 11207 3260 70913964
Porphyrins urine increased 29.18 14.87 5 11215 29 70917195
Respiratory fatigue 29.00 14.87 7 11213 253 70916971
Death 28.97 14.87 23 11197 510038 70407186
Apraxia 28.53 14.87 12 11208 2671 70914553
Skin hyperpigmentation 28.47 14.87 16 11204 6699 70910525
Chronic gastritis 28.20 14.87 13 11207 3600 70913624
Palmoplantar pustulosis 28.13 14.87 8 11212 551 70916673
Acquired porphyria 28.13 14.87 5 11215 37 70917187
Haemophilic arthropathy 27.76 14.87 6 11214 131 70917093
Porphyrins stool increased 27.36 14.87 5 11215 44 70917180
Synovial disorder 26.67 14.87 9 11211 1094 70916130
Helicobacter gastritis 26.54 14.87 11 11209 2360 70914864
Meteoropathy 25.47 14.87 4 11216 12 70917212
Craniocerebral injury 25.24 14.87 13 11207 4578 70912646
Toxic epidermal necrolysis 24.89 14.87 31 11189 39526 70877698
Pregnancy of partner 24.08 14.87 6 11214 248 70916976
Chronic idiopathic pain syndrome 23.84 14.87 4 11216 20 70917204
Femur fracture 23.84 14.87 29 11191 36103 70881121
Joint contracture 23.37 14.87 10 11210 2322 70914902
Neck pain 22.59 14.87 39 11181 66618 70850606
Poor peripheral circulation 22.48 14.87 11 11209 3474 70913750
Tongue oedema 21.47 14.87 13 11207 6246 70910978
Completed suicide 21.11 14.87 5 11215 227130 70690094
Systemic infection 20.73 14.87 13 11207 6644 70910580
Toxicity to various agents 20.73 14.87 18 11202 382154 70535070
Renal function test abnormal 20.61 14.87 11 11209 4163 70913061
Hand fracture 20.51 14.87 12 11208 5415 70911809
Axial spondyloarthritis 20.20 14.87 6 11214 482 70916742
Drug abuse 20.12 14.87 60 11160 147196 70770028
Urticaria 20.02 14.87 64 11156 162985 70754239
Otitis media 19.89 14.87 12 11208 5727 70911497
Disorientation 19.77 14.87 34 11186 57889 70859335
Spinal fracture 19.69 14.87 18 11202 16149 70901075
Hemianopia 19.58 14.87 8 11212 1657 70915567
Postoperative delirium 19.50 14.87 5 11215 232 70916992
Hyperreflexia 19.41 14.87 13 11207 7429 70909795
Costovertebral angle tenderness 19.40 14.87 5 11215 237 70916987
pH body fluid increased 18.94 14.87 4 11216 78 70917146
Sopor 18.87 14.87 24 11196 31243 70885981
Intervertebral disc protrusion 18.84 14.87 20 11200 21483 70895741
Spondylolisthesis 18.17 14.87 9 11211 2917 70914307
Gastrointestinal inflammation 18.15 14.87 12 11208 6711 70910513
Porphyria non-acute 17.71 14.87 6 11214 738 70916486
Cardiac valve sclerosis 17.63 14.87 4 11216 110 70917114
Peritoneal adhesions 17.60 14.87 5 11215 343 70916881
Gastrointestinal submucosal tumour 17.17 14.87 4 11216 124 70917100
Infusion related reaction 17.12 14.87 5 11215 197529 70719695
Prerenal failure 16.93 14.87 9 11211 3377 70913847
Withdrawal syndrome 16.45 14.87 20 11200 24884 70892340
Aortic valve stenosis 16.24 14.87 10 11210 4949 70912275
Face oedema 15.98 14.87 20 11200 25619 70891605
Gastrointestinal ulcer perforation 15.89 14.87 3 11217 32 70917192
Urethral stenosis 15.82 14.87 6 11214 1021 70916203
Intensive care unit acquired weakness 15.81 14.87 7 11213 1764 70915460
Subileus 15.76 14.87 10 11210 5217 70912007
Mucosal ulceration 15.70 14.87 7 11213 1794 70915430
Psychotic behaviour 15.51 14.87 6 11214 1076 70916148
Angioedema 15.23 14.87 33 11187 66577 70850647
Gamma-glutamyltransferase increased 15.05 14.87 28 11192 50657 70866567
Weight increased 14.93 14.87 10 11210 242321 70674903

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