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 51.82 16.02 26 6623 10451 50588024
Apraxia 41.29 16.02 13 6636 1532 50596943
Fixed eruption 39.75 16.02 11 6638 828 50597647
Inflammatory marker increased 37.04 16.02 17 6632 5617 50592858
Disorientation 36.30 16.02 33 6616 35451 50563024
Chronic gastritis 36.03 16.02 13 6636 2321 50596154
Perseveration 35.60 16.02 8 6641 255 50598220
Spinal pain 34.36 16.02 20 6629 10783 50587692
Thrombocytosis 32.61 16.02 15 6634 4981 50593494
Acquired porphyria 31.08 16.02 5 6644 23 50598452
Porphyrins urine increased 31.08 16.02 5 6644 23 50598452
Lumbar vertebral fracture 30.62 16.02 14 6635 4583 50593892
Synovial disorder 30.11 16.02 9 6640 891 50597584
Porphyrins stool increased 29.96 16.02 5 6644 30 50598445
Joint contracture 28.34 16.02 10 6639 1674 50596801
Polymyalgia rheumatica 27.40 16.02 11 6638 2625 50595850
Synovectomy 27.28 16.02 6 6643 173 50598302
Drug abuse 26.69 16.02 36 6613 59810 50538665
Meteoropathy 26.21 16.02 4 6645 12 50598463
Thoracic vertebral fracture 25.87 16.02 12 6637 4061 50594414
Postoperative delirium 25.25 16.02 5 6644 85 50598390
Serum ferritin decreased 24.85 16.02 9 6640 1623 50596852
Ankylosing spondylitis 24.75 16.02 14 6635 7151 50591324
Porphyria non-acute 24.25 16.02 6 6643 291 50598184
Drug interaction 24.11 16.02 69 6580 199552 50398923
Ovulation disorder 23.83 16.02 4 6645 25 50598450
Spinal fracture 23.21 16.02 18 6631 15555 50582920
Aortic valve stenosis 22.82 16.02 10 6639 2965 50595510
Femur fracture 22.23 16.02 26 6623 37438 50561037
Abdominal pain upper 22.15 16.02 58 6591 159251 50439224
Hemianopia 21.83 16.02 7 6642 875 50597600
Product prescribing error 20.47 16.02 19 6630 20942 50577533
Hyperreflexia 20.42 16.02 11 6638 5107 50593368
Subileus 20.28 16.02 9 6640 2750 50595725
Red blood cell sedimentation rate increased 20.15 16.02 22 6627 29394 50569081
Renal function test abnormal 20.00 16.02 9 6640 2840 50595635
Urticaria 19.91 16.02 49 6600 129512 50468963
Withdrawal syndrome 19.25 16.02 17 6632 17573 50580902
Allodynia 19.23 16.02 6 6643 686 50597789
Infected fistula 18.47 16.02 4 6645 107 50598368
Carotid artery stenosis 18.41 16.02 10 6639 4721 50593754
Junctional ectopic tachycardia 18.26 16.02 4 6645 113 50598362
Sopor 17.47 16.02 17 6632 19862 50578613
Angioedema 17.30 16.02 23 6626 37653 50560822
Respiratory tract infection 16.99 16.02 21 6628 31996 50566479
Substance abuse 16.84 16.02 9 6640 4115 50594360
Blood iron decreased 16.39 16.02 13 6636 11602 50586873
Lactic acidosis 16.31 16.02 21 6628 33334 50565141
Spondylolisthesis 16.14 16.02 8 6641 3129 50595346

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 62.41 19.94 18 4720 1289 29568500
Spinal pain 55.69 19.94 23 4715 4841 29564948
Body mass index abnormal 51.18 19.94 10 4728 128 29569661
Oropharyngeal discomfort 50.54 19.94 18 4720 2538 29567251
Vitamin B12 deficiency 49.78 19.94 19 4719 3252 29566537
Oral mucosa erosion 46.56 19.94 13 4725 828 29568961
Mucosal necrosis 44.69 19.94 8 4730 61 29569728
Antiphospholipid antibodies positive 43.77 19.94 10 4728 280 29569509
Eructation 42.68 19.94 18 4720 3988 29565801
Palmoplantar pustulosis 40.97 19.94 8 4730 102 29569687
Ligament calcification 40.93 19.94 9 4729 211 29569578
Neck pain 38.52 19.94 30 4708 21417 29548372
Hand fracture 38.18 19.94 13 4725 1604 29568185
Lip erosion 38.13 19.94 10 4728 502 29569287
Respiratory fatigue 37.88 19.94 7 4731 65 29569724
Coating in mouth 36.97 19.94 7 4731 75 29569714
Sacroiliitis 34.40 19.94 11 4727 1116 29568673
Craniocerebral injury 31.65 19.94 13 4725 2695 29567094
Death 31.64 19.94 8 4730 342076 29227713
Helicobacter gastritis 30.92 19.94 10 4728 1052 29568737
Product prescribing error 29.82 19.94 24 4714 17952 29551837
Otitis media 28.81 19.94 12 4726 2577 29567212
Hepatitis E antibody positive 27.27 19.94 6 4732 141 29569648
Gastrointestinal inflammation 27.08 19.94 12 4726 2996 29566793
Hepatitis E virus test positive 26.23 19.94 6 4732 169 29569620
Immune-mediated adverse reaction 25.15 19.94 7 4731 440 29569349
Chronic idiopathic pain syndrome 24.52 19.94 4 4734 16 29569773
Poor peripheral circulation 24.50 19.94 9 4729 1385 29568404
General physical health deterioration 24.37 19.94 52 4686 102805 29466984
Costovertebral angle tenderness 23.89 19.94 5 4733 92 29569697
Oral pruritus 23.87 19.94 6 4732 254 29569535
Formication 23.63 19.94 9 4729 1531 29568258
Ankylosing spondylitis 23.33 19.94 12 4726 4164 29565625
Pregnancy of partner 22.63 19.94 6 4732 314 29569475
Peritoneal adhesions 22.43 19.94 5 4733 125 29569664
Prerenal failure 22.32 19.94 9 4729 1779 29568010
Personality change 22.14 19.94 12 4726 4626 29565163
Anal fissure 21.47 19.94 10 4728 2798 29566991
Mucosal ulceration 20.42 19.94 7 4731 881 29568908
Intensive care unit acquired weakness 20.01 19.94 7 4731 936 29568853

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 60.78 15.45 33 10446 12588 64475665
Oral mucosa erosion 53.26 15.45 17 10462 1690 64486563
Product prescribing error 49.46 15.45 43 10436 35226 64453027
Body mass index abnormal 46.43 15.45 10 10469 209 64488044
Regurgitation 42.04 15.45 15 10464 2094 64486159
Mucosal necrosis 41.07 15.45 8 10471 99 64488154
Lip erosion 40.99 15.45 13 10466 1266 64486987
Perseveration 40.89 15.45 10 10469 372 64487881
Ligament calcification 40.76 15.45 9 10470 212 64488041
Inflammatory marker increased 40.42 15.45 22 10457 8429 64479824
Immune-mediated adverse reaction 38.42 15.45 11 10468 756 64487497
Ankylosing spondylitis 38.18 15.45 21 10458 8213 64480040
Polymyalgia rheumatica 35.26 15.45 15 10464 3344 64484909
Thrombocytosis 35.26 15.45 19 10460 7137 64481116
Coating in mouth 34.80 15.45 8 10471 227 64488026
Fixed eruption 34.32 15.45 13 10466 2146 64486107
Antiphospholipid antibodies positive 30.78 15.45 9 10470 666 64487587
Sacroiliitis 30.13 15.45 13 10466 2999 64485254
Respiratory fatigue 30.04 15.45 7 10472 211 64488042
Synovectomy 29.55 15.45 7 10472 227 64488026
Chronic gastritis 29.22 15.45 13 10466 3227 64485026
Labelled drug-drug interaction medication error 29.13 15.45 26 10453 22036 64466217
Apraxia 29.07 15.45 12 10467 2483 64485770
Porphyrins urine increased 29.05 15.45 5 10474 29 64488224
Palmoplantar pustulosis 28.85 15.45 8 10471 489 64487764
Oropharyngeal discomfort 28.64 15.45 15 10464 5320 64482933
Death 28.61 15.45 22 10457 482683 64005570
Vitamin B12 deficiency 28.28 15.45 15 10464 5457 64482796
Drug interaction 28.25 15.45 125 10354 361958 64126295
Acquired porphyria 27.99 15.45 5 10474 37 64488216
Synovial disorder 27.77 15.45 9 10470 939 64487314
Porphyrins stool increased 27.22 15.45 5 10474 44 64488209
Hepatitis E antibody positive 27.14 15.45 6 10473 142 64488111
Helicobacter gastritis 27.06 15.45 11 10468 2189 64486064
Hepatitis E virus test positive 26.28 15.45 6 10473 165 64488088
Craniocerebral injury 26.07 15.45 13 10466 4163 64484090
Skin hyperpigmentation 25.76 15.45 15 10464 6536 64481717
Lumbar vertebral fracture 25.42 15.45 14 10465 5488 64482765
Meteoropathy 25.36 15.45 4 10475 12 64488241
Pregnancy of partner 24.01 15.45 6 10473 244 64488009
Chronic idiopathic pain syndrome 23.74 15.45 4 10475 20 64488233
Joint contracture 23.17 15.45 10 10469 2309 64485944
Poor peripheral circulation 23.10 15.45 11 10468 3189 64485064
General physical health deterioration 22.77 15.45 79 10400 204346 64283907
Thoracic vertebral fracture 22.18 15.45 12 10467 4541 64483712
Urticaria 21.98 15.45 63 10416 147254 64340999
Tongue oedema 21.68 15.45 13 10466 5977 64482276
Completed suicide 21.57 15.45 5 10474 224409 64263844
Hand fracture 21.42 15.45 12 10467 4862 64483391
Eructation 21.11 15.45 15 10464 9176 64479077
Axial spondyloarthritis 21.10 15.45 6 10473 402 64487851
Postoperative delirium 20.88 15.45 5 10474 170 64488083
Renal function test abnormal 20.84 15.45 11 10468 3963 64484290
Spinal fracture 20.26 15.45 18 10461 15156 64473097
Otitis media 20.25 15.45 12 10467 5401 64482852
Disorientation 20.03 15.45 34 10445 55794 64432459
Hemianopia 19.98 15.45 8 10471 1531 64486722
Costovertebral angle tenderness 19.81 15.45 5 10474 212 64488041
Toxicity to various agents 19.75 15.45 18 10461 363495 64124758
Hyperreflexia 19.57 15.45 13 10466 7135 64481118
Toxic epidermal necrolysis 19.50 15.45 27 10452 37139 64451114
Neck pain 18.88 15.45 35 10444 61498 64426755
pH body fluid increased 18.88 15.45 4 10475 77 64488176
Gastrointestinal inflammation 18.75 15.45 12 10467 6183 64482070
Spondylolisthesis 18.34 15.45 9 10470 2785 64485468
Femur fracture 18.21 15.45 25 10454 34110 64454143
Porphyria non-acute 17.74 15.45 6 10473 715 64487538
Haemophilic arthropathy 17.66 15.45 4 10475 106 64488147
Peritoneal adhesions 17.61 15.45 5 10474 333 64487920
Cardiac valve sclerosis 17.59 15.45 4 10475 108 64488145
Prerenal failure 17.13 15.45 9 10470 3213 64485040
Gastrointestinal submucosal tumour 17.09 15.45 4 10475 123 64488130
Aortic valve stenosis 16.73 15.45 10 10469 4570 64483683
Suspected transmission of an infectious agent via product 16.31 15.45 6 10473 913 64487340
Face oedema 16.11 15.45 20 10459 24741 64463512
Subileus 15.96 15.45 10 10469 4967 64483286
Urethral stenosis 15.90 15.45 6 10473 980 64487273
Gastrointestinal ulcer perforation 15.81 15.45 3 10476 32 64488221
Mucosal ulceration 15.80 15.45 7 10472 1720 64486533
Intensive care unit acquired weakness 15.80 15.45 7 10472 1720 64486533
Psychotic behaviour 15.65 15.45 6 10473 1023 64487230

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