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

Stem definitionDrug idCAS RN
selective cyclo-oxygenase inhibitors 2397 162011-90-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • rofecoxib
  • vioxx
  • ceeoxx
a sulfonylphenyl furanone; withdrawn out of concern for TOXICITY
  • Molecular weight: 314.36
  • Formula: C17H14O4S
  • CLOGP: 1.80
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 60.44
  • ALOGS: -4.47
  • ROTB: 3

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
25 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.65 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 93 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.13 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
May 20, 1999 FDA

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 hypersensitivity 617.49 41.34 293 2616 250717 50351498
Stress 174.59 41.34 77 2832 53716 50548499
Oesophageal spasm 101.11 41.34 24 2885 2272 50599943
Oesophageal pain 96.35 41.34 24 2885 2778 50599437
Drug ineffective 91.42 41.34 165 2744 819168 49783047
Nasopharyngitis 86.02 41.34 78 2831 192849 50409366
Anaphylactic reaction 81.39 41.34 46 2863 54009 50548206
Drug intolerance 72.09 41.34 75 2834 219029 50383186
Spinal cord infection 70.46 41.34 14 2895 573 50601642
Lymphoedema 68.39 41.34 24 2885 9098 50593117
Bone erosion 52.03 41.34 21 2888 11666 50590549
Sleep apnoea syndrome 51.96 41.34 26 2883 23842 50578373
Tinnitus 50.74 41.34 27 2882 28105 50574110
Hepatic fibrosis 46.86 41.34 14 2895 3188 50599027
Impaired work ability 45.63 41.34 20 2889 13620 50588595

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
Acne cystic 252.06 57.25 37 873 460 29573157
Abdominal discomfort 94.34 57.25 40 870 47863 29525754
Drug intolerance 84.08 57.25 37 873 48342 29525275
Insomnia 81.98 57.25 44 866 88717 29484900
Drug ineffective 75.42 57.25 72 838 363098 29210519
Ankylosing spondylitis 71.27 57.25 18 892 4158 29569459
Sacroiliitis 70.15 57.25 14 896 1113 29572504

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
Drug hypersensitivity 507.85 44.42 233 2625 237582 64258292
Stress 181.78 44.42 76 2782 60458 64435416
Nasopharyngitis 118.58 44.42 85 2773 195988 64299886
Oesophageal spasm 115.89 44.42 26 2832 2499 64493375
Oesophageal pain 109.25 44.42 26 2832 3237 64492637
Drug ineffective 108.75 44.42 157 2701 840090 63655784
Anaphylactic reaction 82.30 44.42 46 2812 68618 64427256
Lymphoedema 80.68 44.42 26 2832 9879 64485995
Drug intolerance 77.44 44.42 65 2793 187927 64307947
Sleep apnoea syndrome 65.13 44.42 30 2828 29802 64466072
Therapeutic product effect decreased 58.28 44.42 45 2813 115306 64380568
Ankylosing spondylitis 52.60 44.42 18 2840 8216 64487658
Sacroiliitis 51.31 44.42 14 2844 2998 64492876
Bone erosion 50.17 44.42 19 2839 11576 64484298
Tinnitus 49.57 44.42 26 2832 34107 64461767
Impaired work ability 48.53 44.42 20 2838 15199 64480675
Fibromyalgia 48.45 44.42 26 2832 35705 64460169
Chest expansion decreased 46.67 44.42 8 2850 187 64495687
Therapeutic product effect incomplete 45.03 44.42 37 2821 103445 64392429
C-reactive protein abnormal 44.68 44.42 23 2835 29024 64466850

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AH02 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|

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Migraine indication 37796009 DOID:6364
Rheumatoid arthritis indication 69896004 DOID:7148
Dysmenorrhea indication 266599000
Osteoarthritis indication 396275006
Juvenile rheumatoid arthritis indication 410795001




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

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 6.51 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 5.77 CHEMBL
Prostaglandin E2 receptor EP2 subtype GPCR Ki 7.47 PDSP
Cytochrome c oxidase subunit 2 Enzyme IC50 5.52 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 7.92 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 4.63 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.37 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.12 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 4.94 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.52 CHEMBL

External reference:

IDSource
4021160 VUID
N0000148611 NUI
D00568 KEGG_DRUG
4021160 VANDF
C0762662 UMLSCUI
CHEBI:8887 CHEBI
RCX PDB_CHEM_ID
CHEMBL122 ChEMBL_ID
DB00533 DRUGBANK_ID
C116926 MESH_SUPPLEMENTAL_RECORD_UI
5090 PUBCHEM_CID
2893 IUPHAR_LIGAND_ID
7768 INN_ID
0QTW8Z7MCR UNII
232158 RXNORM
30883 MMSL
8220 MMSL
d04433 MMSL
007787 NDDF
116095002 SNOMEDCT_US
387008005 SNOMEDCT_US

Pharmaceutical products:

None