diflunisal

Trade name: dolobid

Small moleculeapproved

Approved

Apr 19, 1982

Diflunisal is a salicylic acid derivative with analgesic and anti-inflammatory activity. It was developed by Merck Sharp & Dohme in 1971 after showing promise in a research project studying more potent chemical analogs of aspirin. Diflunisal is an aspirin-like nonsteroidal anti-inflammatory drug that inhibits cyclooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis.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. — NCATS

Clinical trial activity

4 trials · 7 clinical orgs · 10 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Feb 1, 2006 (NCT00294671)

Timeline

1980s

Apr 19, 1982
Merck — Earliest FDA Approval
Apr 19, 1982
Merck — NDA Organization

1990s

Jul 31, 1992
Teva — Marketing Organization
Nov 27, 1992
DASTECH INTL — Marketing Organization
Nov 27, 1992
Socorro Pharmaceuticals — Marketing Organization
May 7, 1996
Puracap Pharmaceutical — Marketing Organization
Jun 10, 1996
Ani Pharmaceuticals — Marketing Organization
Jul 17, 1997
Watson Pharmaceuticals — Marketing Organization

2000s

Jan 1, 2006
Earliest Phase 2 Sponsor(trial)

2010s

Mar 8, 2012
Heritage Pharma — Marketing Organization
Mar 8, 2012
Emcure — Marketing Organization
Jun 16, 2017
Zydus Discovery DMCC — Marketing Organization
Jan 1, 2019
Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

CyclooxygenaseINHIBITOR
Cyclooxygenase inhibitor
- Prostaglandin G/H synthase 2 (PTGS2) ↗
- Prostaglandin G/H synthase 1 (PTGS1) ↗
- Cyclooxygenase-1
- Cyclooxygenase-2

Approval history

approvedPriority reviewApr 19, 1982

Chemistry & pharmacology

Loading structure…

SMILES

OC(=O)C1=C(O)C=CC(=C1)C2=CC=C(F)C=C2F

Mol. weight: 250.1976 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Achiral Molecule
Inorganic: No
Polymer: No
Delivery: Oral
Availability: Prescription Only

Oral

Yes

Parenteral

Topical

Black box warning

Sources

Also known as

2',4'-difluoro-4-hydroxy-3-biphenylcarboxylic acid
2',4'-difluoro-4-hydroxy-3-biphenylcarboxylic acid
2-(hydroxy)-5-(2,4-difluorophenyl)benzoic acid
2-(hydroxy)-5-(2,4-difluorophenyl)benzoic acid
5-(2,4-difluorophenyl)salicylic acid
5-(2,4-difluorophenyl)salicylic acid
difludol
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisal
diflunisalum
diflunisalum
difluorophenylsalicylic acid
diflusinal
dolobid
dolobid
dolobid
dolobid 500
fluniget
fluodonil
mk-647

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT04113668	Phase 1	Oct 1, 2019	Bristol-Myers Squibb
NCT01676363	Phase 4	Mar 1, 2013	University of British Columbia
NCT00506298	Phase 2	Jul 1, 2007	Medicor Research Inc., Zalicus
NCT00294671	Phase 2/Phase 3 (Phase 3)	Feb 1, 2006	Boston University, Food and Drug Administration, National Institute of Neurological Disorders and Stroke (NINDS)

Showing 4 of 4 trials

Page 1 / 1

Organizations

Research & Development (7)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Boston University	Academic/Hospital	1	1	1	2006
Bristol-Myers Squibb	For profit	1	1	1	2019
Food and Drug Administration	Government	1	0	1	2006
Medicor Research Inc.	For profit	1	0	1	2007
National Institute of Neurological Disorders and Stroke (NINDS)	Government	1	0	1	2006
University of British Columbia	Academic/Hospital	1	1	1	2013
Zalicus	For profit	1	1	1	2007

7 organizations

Page 1 / 1

Marketing (11)

Organization	Org type	Relationship	Date
Ani Pharmaceuticals	For profit	SYN	Jun 10, 1996
Ani Pharmaceuticals	For profit	MKTG	Jun 10, 1996
DASTECH INTL	For profit	MKTG	Nov 27, 1992
Emcure	For profit	MKTG	Mar 8, 2012
Heritage Pharma	For profit	MKTG	Mar 8, 2012
Merck	For profit	NDA	Apr 19, 1982
Puracap Pharmaceutical	For profit	MKTG	May 7, 1996
Socorro Pharmaceuticals	For profit	MKTG	Nov 27, 1992
Teva	For profit	MKTG	Jul 31, 1992
Watson Pharmaceuticals	For profit	MKTG	Jul 17, 1997
Zydus Discovery DMCC	For profit	MKTG	Jun 16, 2017