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
Drug abuse 65.19 38.17 19 316 12007 2345743
Disorientation 52.50 38.17 14 321 6358 2351392
Subileus 51.35 38.17 9 326 562 2357188
Nausea 49.13 38.17 29 306 112160 2245590
Intestinal perforation 41.08 38.17 9 326 1782 2355968
Metastases to bone 38.96 38.17 9 326 2260 2355490
Haematemesis 38.52 38.17 10 325 4072 2353678

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
Toxic epidermal necrolysis 76.28 45.47 16 211 2355 1744199
Acute kidney injury 60.65 45.47 24 203 34920 1711634

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 drug

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

Pharmaceutical products:

None