etoricoxib 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 ┬ÁM/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
Disorientation 43.43 15.32 41 7644 36877 46641500
Drug interaction 43.29 15.32 100 7585 202994 46475383
Apraxia 41.27 15.32 14 7671 1661 46676716
Perseveration 33.80 15.32 8 7677 255 46678122
Acquired porphyria 29.95 15.32 5 7680 23 46678354
Porphyrins urine increased 29.95 15.32 5 7680 23 46678354
Chronic gastritis 29.35 15.32 12 7673 2391 46675986
Spinal pain 29.33 15.32 19 7666 9873 46668504
Porphyrins stool increased 28.84 15.32 5 7680 30 46678347
Synovial disorder 28.70 15.32 9 7676 833 46677544
Drug abuse 28.39 15.32 43 7642 63365 46615012
Lumbar vertebral fracture 27.78 15.32 14 7671 4528 46673849
Postoperative delirium 26.40 15.32 5 7680 52 46678325
Thoracic vertebral fracture 26.22 15.32 13 7672 4062 46674315
Synovectomy 25.83 15.32 6 7679 176 46678201
Meteoropathy 25.31 15.32 4 7681 12 46678365
Ankylosing spondylitis 25.19 15.32 15 7670 6722 46671655
Intervertebral disc protrusion 24.63 15.32 23 7662 20382 46657995
Speech disorder 24.51 15.32 30 7655 36137 46642240
Fixed eruption 24.38 15.32 8 7677 857 46677520
Hemianopia 23.95 15.32 8 7677 905 46677472
Subileus 23.63 15.32 11 7674 2992 46675385
Serum ferritin decreased 22.77 15.32 9 7676 1643 46676734
Ovulation disorder 22.66 15.32 4 7681 27 46678350
Porphyria non-acute 22.16 15.32 6 7679 331 46678046
Spinal fracture 21.93 15.32 19 7666 15286 46663091
Femur fracture 20.84 15.32 28 7657 36969 46641408
Red blood cell sedimentation rate increased 20.61 15.32 22 7663 22867 46655510
Hyperreflexia 20.43 15.32 12 7673 5242 46673135
Aortic valve stenosis 20.20 15.32 10 7675 3114 46675263
Osteoarthritis 19.62 15.32 36 7649 61989 46616388
Infected fistula 17.99 15.32 4 7681 96 46678281
Hyperthyroidism 17.71 15.32 15 7670 11696 46666681
Inflammatory marker increased 17.43 15.32 11 7674 5464 46672913
Skin ulcer 17.42 15.32 24 7661 32434 46645943
Sopor 16.01 15.32 18 7667 19810 46658567
Urticaria 15.85 15.32 49 7636 117843 46560534
Respiratory tract infection 15.84 15.32 22 7663 29950 46648427
Thyroid cancer recurrent 15.61 15.32 3 7682 34 46678343
Carotid artery stenosis 15.58 15.32 10 7675 5110 46673267

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
Body mass index abnormal 55.08 18.49 10 5080 78 29947310
Spinal pain 52.88 18.49 22 5068 4442 29942946
Ligament calcification 51.63 18.49 9 5081 54 29947334
Oral mucosa erosion 46.15 18.49 13 5077 805 29946583
Mucosal necrosis 43.45 18.49 8 5082 68 29947320
Antiphospholipid antibodies positive 43.02 18.49 10 5080 285 29947103
Palmoplantar pustulosis 42.56 18.49 8 5082 77 29947311
Respiratory fatigue 37.46 18.49 7 5083 65 29947323
Coating in mouth 36.81 18.49 7 5083 72 29947316
General physical health deterioration 36.78 18.49 63 5027 99881 29847507
Hand fracture 36.74 18.49 13 5077 1694 29945694
Sacroiliitis 36.69 18.49 11 5079 849 29946539
Lip erosion 35.82 18.49 10 5080 599 29946789
Product prescribing error 34.44 18.49 26 5064 16707 29930681
Ankylosing spondylitis 33.33 18.49 16 5074 4518 29942870
Gastrointestinal inflammation 29.97 18.49 13 5077 2906 29944482
Drug interaction 28.21 18.49 86 5004 199482 29747906
Otitis media 28.21 18.49 12 5078 2559 29944829
Craniocerebral injury 27.09 18.49 12 5078 2821 29944567
Formication 25.64 18.49 10 5080 1707 29945681
Psoriatic arthropathy 24.96 18.49 21 5069 15740 29931648
Death 24.95 18.49 15 5075 357268 29590120
Immune-mediated adverse reaction 24.31 18.49 7 5083 469 29946919
Oral pruritus 23.42 18.49 6 5084 258 29947130
Poor peripheral circulation 22.72 18.49 9 5081 1601 29945787
Anal fissure 22.45 18.49 10 5080 2381 29945007
Skin exfoliation 21.57 18.49 23 5067 23149 29924239
Impaired healing 20.45 18.49 18 5072 14322 29933066
Intensive care unit acquired weakness 20.14 18.49 7 5083 865 29946523
Mucosal ulceration 20.09 18.49 7 5083 871 29946517
Hyperhidrosis 19.22 18.49 38 5052 67052 29880336
Sialadenosis 18.88 18.49 3 5087 9 29947379
Toxic epidermal necrolysis 18.84 18.49 19 5071 17921 29929467
Endocarditis 18.54 18.49 12 5078 6031 29941357

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 drugs
CHEBI has role CHEBI:50629 cyclooxygenase-2 inhibitor

Drug Use (View source of the data)

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 E2 receptor EP2 subtype GPCR Ki 7.10 PDSP
Prostaglandin G/H synthase 1 Enzyme IC50 4.92 CHEMBL
Mitogen-activated protein kinase 14 Kinase IC50 6.28 CHEMBL

External reference:

IDSource
D03710 KEGG_DRUG
C1530229 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