Drug/Small Molecule:
diflunisal

2D structure

Overview

Trade Names: Adomal; Difludol; Dolisal; Dolobid; Dolobil; Dolobis; Flovacil; Fluniget; Fluodonil; Flustar
PharmGKB Accession Id: PA449313

Description

A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of aspirin. PubChem (source: Drug Bank)

Indication

For acute or long-term use for symptomatic treatment of mild to moderate pain, osteoarthritis, and rheumatoid arthritis. (source: Drug Bank)

ATC Therapeutic Category

  • N02BA:Salicylic acid and derivatives

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

The precise mechanism of the analgesic and anti-inflammatory actions of diflunisal is not known. Diflunisal is a prostaglandin synthetase inhibitor. In animals, prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain. Since prostaglandins are known to be among the mediators of pain and inflammation, the mode of action of diflunisal may be due to a decrease of prostaglandins in peripheral tissues. (source: Drug Bank)

Pharmacology

Diflunisal is a nonsteroidal drug with analgesic, anti-inflammatory and antipyretic properties. It is a peripherally-acting non-narcotic analgesic drug. Habituation, tolerance and addiction have not been reported. Diflunisal is a difluorophenyl derivative of salicylic acid. Chemically, diflunisal differs from aspirin (acetylsalicylic acid) in two respects. The first of these two is the presence of a difluorophenyl substituent at carbon 1. The second difference is the removal of the 0-acetyl group from the carbon 4 position. Diflunisal is not metabolized to salicylic acid, and the fluorine atoms are not displaced from the difluorophenyl ring structure. (source: Drug Bank)

Food Interactions

Avoid alcohol.
Take with food to reduce irritation. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic, primarily via glucuronide conjugation (90% of administered dose). (source: Drug Bank)

Protein Binding

More than 99% of diflunisal in plasma is bound to proteins. (source: Drug Bank)

Absorption

Rapidly and completely absorbed following oral administration, with a bioavailability of 80-90%. (source: Drug Bank)

Toxicity

Oral LD<sub>50</sub> in rat, mouse, and rabbit is 392 mg/kg, 439 mg/kg, and 603 mg/kg, respectively. Symptoms of overdose include coma, tachycardia, stupor, and vomiting. The lowest dose without the presence of other medicines which caused death was 15 grams. (source: Drug Bank)

Isomeric SMILES Code:

c1cc(c(cc1c2ccc(cc2F)F)C(=O)O)O (source: Drug Bank)

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
ALB Uncurated Annotation (source: Drug Bank)
PTGS1 Uncurated Annotation (source: Drug Bank)
PTGS2 Uncurated Annotation (source: Drug Bank)
TTR Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)
alendronate Uncurated Annotation Increased risk of gastric toxicity (source: Drug Bank)
dicumarol Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)
indomethacin Uncurated Annotation Increases the effect and toxicity of indomethacin (source: Drug Bank)
probenecid Uncurated Annotation Probenecid increases toxicity of diflunisal (source: Drug Bank)
warfarin Uncurated Annotation The NSAID increases the anticoagulant effect (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00861
ChEBI ID:
4538
KEGG Compound ID:
C01691
KEGG Drug ID:
D00130
PubChem Compound ID:
3059
PubChem Substance ID:
4832

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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