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

Stem definitionDrug idCAS RN
analgesic anti-inflammatory 880 22494-42-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • diflunisal
  • difludol
  • diflusinal
  • fluniget
  • fluodonil
  • difluorophenylsalicylic acid
  • MK-647
A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.
  • Molecular weight: 250.20
  • Formula: C13H8F2O3
  • CLOGP: 4.40
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 57.53
  • ALOGS: -3.55
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.75 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 6 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 99.92 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 85 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.00 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 19, 1982 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
Completed suicide 69.10 57.21 13 13 21021 2337038

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

Pharmacologic Action:

SourceCodeDescription
ATC N02BA11 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Salicylic acid and derivatives
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35481 non-narcotic analgesic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
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
Chronic pain indication 82423001
Osteoarthritis indication 396275006
Arthritis off-label use 3723001 DOID:848
Vascular headache off-label use 128187005
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
Breastfeeding (mother) contraindication 413712001
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.81 acidic
pKa2 12.64 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 1 Enzyme INHIBITOR IC50 4.40 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 5.09 WOMBAT-PK CHEMBL
Carbonic anhydrase 2 Enzyme Ki 5.03 CHEMBL
Carbonic anhydrase 1 Enzyme Ki 5.07 CHEMBL
Transthyretin Secreted Kd1 7.13 WOMBAT-PK

External reference:

IDSource
D004061 MESH_DESCRIPTOR_UI
4017950 VUID
N0000146300 NUI
C0012228 UMLSCUI
D00130 KEGG_DRUG
7C546U4DEN UNII
3774 INN_ID
1247 MMSL
3393 RXNORM
387116004 SNOMEDCT_US
4595 MMSL
d00208 MMSL
20865003 SNOMEDCT_US
4017950 VANDF
001599 NDDF
CHEBI:39669 CHEBI
CHEMBL898 ChEMBL_ID
DB00861 DRUGBANK_ID
1FL PDB_CHEM_ID
7162 IUPHAR_LIGAND_ID
3059 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 0093-0755 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 14539-673 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
DIFLUNISAL HUMAN PRESCRIPTION DRUG LABEL 1 52959-379 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 54868-3049 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 60760-756 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
DIFLUNISAL HUMAN PRESCRIPTION DRUG LABEL 1 64980-181 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 68151-0848 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 68382-530 TABLET 500 mg ORAL ANDA 15 sections
Diflunisal HUMAN PRESCRIPTION DRUG LABEL 1 70771-1083 TABLET 500 mg ORAL ANDA 14 sections