ContaminantDB: Diflunisal

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:51 UTC

Update Date

2026-05-14 16:51:00 UTC

Accession Number

CHEM002292

Identification

Common Name

Diflunisal

Class

Small Molecule

Description

Diflunisal, a salicylate derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with pharmacologic actions similar to other prototypical NSAIAs. Diflunisal possesses anti-inflammatory, analgesic and antipyretic activity. Though its mechanism of action has not been clearly established, most of its actions appear to be associated with inhibition of prostaglandin synthesis via the arachidonic acid pathway. Diflunisal is used to relieve pain accompanied with inflammation and in the symptomatic treatment of rheumatoid arthritis and osteoarthritis.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anti-Inflammatory Agent, Non-Steroidal
Cyclooxygenase Inhibitor
Drug
Ester
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2',4'-Difluoro-4-hydroxy-3-biphenylcarboxylic acid	ChEBI
2-(Hydroxy)-5-(2,4-difluorophenyl)benzoic acid	ChEBI
5-(2,4-Difluorophenyl)salicylic acid	ChEBI
Dolobid	ChEBI
2',4'-Difluoro-4-hydroxy-3-biphenylcarboxylate	Generator
2-(Hydroxy)-5-(2,4-difluorophenyl)benzoate	Generator
5-(2,4-Difluorophenyl)salicylate	Generator
Diflunisal novopharm brand	HMDB
Dolocid	HMDB
Frosst sa brand OF diflunisal	HMDB
Novopharm brand OF diflunisal	HMDB
Nu pharm brand OF diflunisal	HMDB
Nu-diflunisal	HMDB
Merck brand OF diflunisal	HMDB
Novo-diflunisal	HMDB
Apo-diflunisal	HMDB
Dolobis	HMDB
Merck sharp and dohme brand OF diflunisal	HMDB
Nu-pharm brand OF diflunisal	HMDB
Apotex brand OF diflunisal	HMDB
Cahill may roberts brand OF diflunisal	HMDB
Apo diflunisal	HMDB
ApoDiflunisal	HMDB
Novo diflunisal	HMDB
Nu diflunisal	HMDB
NovoDiflunisal	HMDB
NuDiflunisal	HMDB

Chemical Formula

C₁₃H₈F₂O₃

Average Molecular Mass

250.198 g/mol

Monoisotopic Mass

250.044 g/mol

CAS Registry Number

22494-42-4

IUPAC Name

2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylic acid

Traditional Name

diflunisal

SMILES

OC(=O)C1=C(O)C=CC(=C1)C1=C(F)C=C(F)C=C1

InChI Identifier

InChI=1S/C13H8F2O3/c14-8-2-3-9(11(15)6-8)7-1-4-12(16)10(5-7)13(17)18/h1-6,16H,(H,17,18)

InChI Key

HUPFGZXOMWLGNK-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Fluorobenzene
Halobenzene
Phenol
Aryl fluoride
Aryl halide
Vinylogous acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organohalogen compound
Organofluoride
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:39669 )
monohydroxybenzoic acid (CHEBI:39669 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Diflunisal Pathway	Not Available	Not Available

Applications

Biological Roles

non-narcotic analgesic

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	210-211°C
Boiling Point	Not Available
Solubility	Practically insoluble (14.5 mg/L) at neutral or acidic pH.

Predicted Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	3.11	ALOGPS
logP	3.91	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.86 m³·mol⁻¹	ChemAxon
Polarizability	22.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pc0-1190000000-37ea5d58644c01ef5b1e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05fr-5019000000-223530358c78521d8313	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-2690000000-64056c9dc4e2f14d3c59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4j-5590000000-462ea99995ea9238bf94	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-5490000000-ec23e03578a95364b748	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9550000000-2fa065aea811fa7b6c5a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000t-9000000000-01d2c7c75ab3756b3df7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090000000-e1009fb8e100faed2065	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0090000000-e9bcdf3ba0212ee28f45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fc0-1970000000-baed3c5d64825d6b04b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-0090000000-6427bf95a0116aa621f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-83af00a8dd308410951d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0690000000-a756057c6442130830ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0090000000-645b3ae2575f11227813	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-78fd25facb031cdb643f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-0940000000-9920437171fca6936f28	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-3e0ed3bddcaf7a500b10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-0090000000-4ac100e6866826f4e00a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kdi-1930000000-6c51e381123d99125d70	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fai-1690000000-d231ff5a9ac7d9769d2d	Spectrum

Toxicity Profile

Route of Exposure

Rapidly and completely absorbed following oral administration, with a bioavailability of 80-90%. Peak plasma concentrations are achieved 2 - 3 hours following oral administration.

Mechanism of Toxicity

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.

Metabolism

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 Values

LD50: 392 mg/kg (Oral, Rat) (1) LD50: 439 mg/kg (Oral, Mouse) (1) LD50: 603 mg/kg (Oral, Rabbit) (1)

Lethal Dose

The lowest dose without the presence of other medicines which caused death was 15 grams.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used to relieve pain, tenderness, swelling and stiffness caused by osteoarthritis (arthritis caused by a breakdown of the lining of the joints) and rheumatoid arthritis (arthritis caused by swelling of the lining of the joints). [L1869]

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include coma, tachycardia, stupor, and vomiting.

Treatment

In the event of overdosage, the stomach should be emptied by inducing vomiting or by gastric lavage, and the patient carefully observed and given symptomatic and supportive treatment. Because of the high degree of protein binding, hemodialysis may not be effective. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00861

HMDB ID

HMDB0014999

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID