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QuickView for Diflunisal (compound)

Name: Diflunisal
PubChem Compound ID: 3059
Description: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.
Molecular formula: C13H8F2O3
Molecular weight: 250.198 g/mol
Diflunisal; [1,1'-Biphenyl]-3-carboxylic acid, 2',4'-difluoro-4-hydroxy-; KBio2_001442; Spectrum2_001012; MK-647; Spectrum4_000513; KBio2_006578; KBioGR_001085; KBioSS_001442; CAS-22494-42-4.
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Name: Diflunisal
Name (isomeric): DB00861
Drug Type: small molecule
Description: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN.
Brand: Fluodonil, Flovacil, Difludol, Dolisal, Dolobis, Dolobid, Flustar, Adomal, Fluniget, Dolobil
Category: Analgesics, Non-Narcotic, Antipyretics, Cyclooxygenase Inhibitors, Analgesics, Anti-inflammatory Agents, Nonsteroidal Anti-inflammatory Agents (NSAIAs)
CAS number: 22494-42-4
Indication: For symptomatic treatment of mild to moderate pain accompanied by inflammation (e.g. musculoskeletal trauma, post-dental extraction, post-episiotomy), osteoarthritis, and rheumatoid arthritis.
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 r...
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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 mod...
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Absorption: Rapidly and completely absorbed following oral administration, with a bioavailability of 80-90%. Peak plasma concentrations are achieved 2 - 3 hours following oral administration.
Protein binding: At least 98 to 99% of diflunisal in plasma is bound to proteins.
Biotransformation: Hepatic, primarily via glucuronide conjugation (90% of administered dose).
Route of elimination: The drug is excreted in the urine as two soluble glucuronide conjugates accounting for about 90% of the administered dose. Little or no diflunisal is excreted in the feces.
Half Life: 8 to 12 hours
Toxicity: Oral LD50 in rat, mouse, and rabbit is 392 mg/kg, 439 mg/kg, and 603 mg/kg, respectively. Symptoms of overdose include drowsiness, nausea, vomiting, diarrhea, hyperventilation, tachycardia, sweating, tinnitus, disorientation, stupor, and coma. The lowest dose without the presence of other medicines which caused death was 15 grams.

Selective COX-2 inhibitors have been associated with increased risk of serious cardiovascular events (e.g. myocardial infarction, stroke) in some patients. Current data is insufficient to assess the cardiovascular risk of diflunisal. Short-term use does not appear to be associated with increased cardiovascular risk (except when used immediately following coronary artery bypass graft (CABG) surgery). Risk of GI toxicity including bleeding, ulceration and perforation. Risk of direct renal injury, including renal papillary necrosis. Severe hepatic reactions, including cholestasis and/or jaundice, have been reported. May cause rash or hypersensitivity syndrome.

Affected organisms: Humans and other mammals
Food interaction:
Avoid alcohol.
Food slightly delays rate of absorption with no effect on extent of absorption.
Take with food to reduce gastric irritation.
Drug interaction:
AnisindioneThe NSAID, diflunisal, may increase the anticoagulant effect of anisindione.
DicumarolThe NSAID, diflunisal, may increase the anticoagulant effect of dicumarol.
LithiumThe NSAID, diflunisal, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
IndomethacinConcomitant therapy with the two NSAIDs, indomethacin and diflunisal, increases the risk of NSAID-related adverse effects (e.g. GI ulcers, bleeds, increased blood pressure).
TrandolaprilThe NSAID, Diflunisal, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Diflunisal is initiated, discontinued or dose changed.
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