etodolac Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory agents, ibufenac derivatives 1103 41340-25-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • etodolac
  • etodine
  • etodolic acid
  • hypen
A non-steroidal anti-inflammatory agent and cyclooxygenase-2 (COX-2) inhibitor with potent analgesic and anti-arthritic properties. It has been shown to be effective in the treatment of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; ANKYLOSING SPONDYLITIS; and in the alleviation of postoperative pain (PAIN, POSTOPERATIVE).
  • Molecular weight: 287.36
  • Formula: C17H21NO3
  • CLOGP: 3.43
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 62.32
  • ALOGS: -3.87
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 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) 69.60 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Jan. 31, 1991 FDA WYETH PHARMS INC

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 66.02 13.57 124 6762 243701 46435475
Interstitial lung disease 49.98 13.57 50 6836 53899 46625277
Hepatic function abnormal 43.65 13.57 38 6848 34383 46644793
Pneumocystis jirovecii pneumonia 28.19 13.57 21 6865 15227 46663949
Liver disorder 28.18 13.57 31 6855 37215 46641961
Psoriatic arthropathy 22.03 13.57 27 6859 36352 46642824
Altered state of consciousness 18.65 13.57 20 6866 23328 46655848
Aspartate aminotransferase increased 17.55 13.57 37 6849 78663 46600513
Disseminated intravascular coagulation 16.46 13.57 17 6869 18988 46660188
Beta-N-acetyl-D-glucosaminidase increased 15.56 13.57 3 6883 39 46679137
Blood lactate dehydrogenase increased 15.39 13.57 17 6869 20483 46658693
Herpes zoster 15.23 13.57 32 6854 67840 46611336
Organising pneumonia 14.42 13.57 9 6877 4893 46674283

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
Interstitial lung disease 55.42 16.08 53 3932 60144 29888349
Gastric haemorrhage 45.13 16.08 23 3962 9444 29939049
Gastric ulcer 40.08 16.08 25 3960 15096 29933397
Gastrointestinal haemorrhage 36.54 16.08 50 3935 83396 29865097
Duodenal ulcer 25.30 16.08 16 3969 9885 29938608
Erythema multiforme 23.18 16.08 14 3971 7971 29940522
Blood alkaline phosphatase increased 22.13 16.08 24 3961 31463 29917030
Atypical femur fracture 18.71 16.08 5 3980 326 29948167
Hepatic function abnormal 18.12 16.08 25 3960 41920 29906573
Palmar-plantar erythrodysaesthesia syndrome 17.39 16.08 15 3970 14855 29933638
Rectal haemorrhage 16.89 16.08 22 3963 34917 29913576
Blood lactate dehydrogenase increased 16.79 16.08 17 3968 20584 29927909
Aspartate aminotransferase increased 16.55 16.08 30 3955 63392 29885101
Renal cell carcinoma 16.46 16.08 10 3975 5756 29942737

Pharmacologic Action:

SourceCodeDescription
ATC M01AB08 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Acetic acid derivatives and related substances
FDA CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:35493 anti-pyretic
CHEBI has role CHEBI:50629 cyclooxygenase-2 inhibitor
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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Rheumatoid arthritis indication 69896004 DOID:7148
Osteoarthritis indication 396275006
Juvenile rheumatoid arthritis indication 410795001
Ankylosing spondylitis off-label use 9631008 DOID:7147
Tendinitis off-label use 34840004 DOID:971
Bursitis off-label use 84017003 DOID:2965
Gout off-label use 90560007 DOID:13189
Peptic ulcer contraindication 13200003 DOID:750
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.95 acidic
pKa2 11.17 acidic

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 5.70 CHEMBL CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 5.58 DRUG MATRIX

External reference:

IDSource
4019559 VUID
N0000147659 NUI
D00315 KEGG_DRUG
4019559 VANDF
C0059865 UMLSCUI
CHEBI:4909 CHEBI
CHEMBL622 ChEMBL_ID
DB00749 DRUGBANK_ID
D017308 MESH_DESCRIPTOR_UI
3308 PUBCHEM_CID
7185 IUPHAR_LIGAND_ID
3715 INN_ID
2M36281008 UNII
24605 RXNORM
4707 MMSL
8937 MMSL
d00851 MMSL
003587 NDDF
108510003 SNOMEDCT_US
386860005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 0093-1118 TABLET, FILM COATED, EXTENDED RELEASE 600 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 0093-1122 TABLET, FILM COATED, EXTENDED RELEASE 400 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 0093-7172 TABLET, FILM COATED, EXTENDED RELEASE 500 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 0185-0675 TABLET, COATED 400 mg ORAL ANDA 26 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 0185-0687 TABLET, COATED 500 mg ORAL ANDA 26 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 10544-862 TABLET, FILM COATED 400 mg ORAL ANDA 30 sections
ETODOLAC HUMAN PRESCRIPTION DRUG LABEL 1 16590-092 TABLET 400 mg ORAL ANDA 30 sections
ETODOLAC HUMAN PRESCRIPTION DRUG LABEL 1 16590-488 CAPSULE 300 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 16714-497 TABLET, EXTENDED RELEASE 400 mg ORAL ANDA 28 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 16714-498 TABLET, EXTENDED RELEASE 500 mg ORAL ANDA 28 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 16714-499 TABLET, EXTENDED RELEASE 600 mg ORAL ANDA 28 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 21695-049 CAPSULE, GELATIN COATED 300 mg ORAL ANDA 27 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 21695-050 TABLET, FILM COATED 400 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 33261-043 TABLET, FILM COATED 400 mg ORAL ANDA 28 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 33261-044 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 35356-711 TABLET, FILM COATED 400 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 42254-052 TABLET, FILM COATED 400 mg ORAL ANDA 28 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 42254-121 CAPSULE 300 mg ORAL ANDA 14 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 42291-404 CAPSULE 200 mg ORAL ANDA 26 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 42291-405 CAPSULE 300 mg ORAL ANDA 26 sections
ETODOLAC HUMAN PRESCRIPTION DRUG LABEL 1 42549-511 TABLET, FILM COATED 400 mg ORAL ANDA 30 sections
Etodolac Human Prescription Drug Label 1 42799-111 TABLET, FILM COATED 400 mg ORAL ANDA 25 sections
Etodolac Human Prescription Drug Label 1 42799-112 TABLET, FILM COATED 500 mg ORAL ANDA 25 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43063-578 TABLET, FILM COATED 400 mg ORAL ANDA 31 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43063-671 TABLET, FILM COATED 500 mg ORAL ANDA 31 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43063-834 TABLET, COATED 400 mg ORAL ANDA 27 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43063-856 TABLET, FILM COATED 400 mg ORAL ANDA 31 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43353-294 CAPSULE 300 mg ORAL ANDA 26 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43353-749 TABLET, FILM COATED 500 mg ORAL ANDA 30 sections
Etodolac HUMAN PRESCRIPTION DRUG LABEL 1 43353-752 TABLET, FILM COATED 400 mg ORAL ANDA 30 sections