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sulindac

Trade name: clinoril

Small moleculeapproved

Approved

Sep 27, 1978

Sulindac is a nonsteroidal anti-inflammatory agent (NSAIA) of the arylalkanoic acid class that is marketed in the U.S. by Merck as Clinoril. Like other NSAIAs, it may be used in the treatment of acute or chronic inflammatory conditions. Sulindac is a prodrug, derived from sulfinylindene, that is converted in vivo to an active sulfide compound by liver enzymes. The sulfide metabolite then undergoes enterohepatic circulation; it is excreted in the bile and then reabsorbed from the intestine. This is thought to help maintain constant blood levels with reduced gastrointestinal side effects. Some studies have shown sulindac to be relatively less irritating to the stomach than other NSAIA's except for drugs of the cyclooxygenase-2 (COX-2) inhibitor class. The exact mechanism of its NSAIA properties is unknown, but it is thought to act on enzymes COX-1 and COX-2, inhibiting prostaglandin synthesis. — NCATS

Clinical trial activity

40 trials · 42 clinical orgs · 10 marketing orgs

Phase 1
5
Phase 2
32
Phase 3
6
Phase 4
0

Earliest trial started Aug 1, 1996 (NCT00003365)

Timeline

1970s

  1. Sep 27, 1978

    Merck — Earliest FDA Approval

  2. Sep 27, 1978

    Merck — NDA Organization

1980s

  1. Mar 3, 1988

    Watson Pharmaceuticals — Marketing Organization

1990s

  1. Apr 17, 1991

    Sun Pharmaceuticals — Marketing Organization

  2. Aug 30, 1991

    Fosun — Marketing Organization

  3. Aug 30, 1991

    Chartwell Pharmaceuticals — Marketing Organization

  4. Sep 6, 1991

    Epic Pharma Llc — Marketing Organization

  5. Sep 6, 1991

    Radius Health — Marketing Organization

  6. Feb 28, 1992

    Ani Pharmaceuticals — Marketing Organization

  7. Jun 22, 1993

    Mylan — Marketing Organization

  8. Jun 22, 1993

    Rising Pharmaceuticals — Marketing Organization

  9. Jan 1, 1998

    Earliest Phase 3 Sponsor(trial)

  10. Jan 1, 1999

    Earliest Phase 2 Sponsor(trial)

2000s

  1. Jan 1, 2001

    Earliest Phase 1 Sponsor(trial)

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedSep 27, 1978

Chemistry & pharmacology

Loading structure…

SMILES

C[S+]([O-])C1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=CC(F)=CC=C23)C=C1
Mol. weight
356.411 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

No

Black box warningProdrug

Sources

Also known as

  • 1h-indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-(methylsulfonyl)phenyl)methylene)-, (z)-
  • (5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-(n-benzyl)-indene)-acetamide
  • aptosyn
  • aptosyn
  • cis-5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1h-indene-3-acetic acid
  • cis-5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1h-indene-3-acetic acid
  • cis-5-fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid
  • cis-5-fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid
  • clinoril
  • clinoril
  • clinoril
  • clinoril
  • cp248
  • cp 248
  • exisulind
  • exisulind
  • exisulind
  • exisulind
  • exisulind
  • exisulind
  • fgn-1
  • mk231
  • mk231
  • mk231
  • mk231
  • mk231
  • mk231
  • mk 231
  • mk-231
  • osip486823
  • osip 486823
  • osip-486823
  • sulindac
  • sulindac
  • sulindac
  • sulindac
  • sulindac
  • sulindac
  • sulindac
  • sulindac
  • sulindac
  • sulindaco
  • sulindaco
  • sulindac sulfone
  • sulindac sulfone
  • sulindac sulfone
  • sulindac sulfone
  • sulindac sulfone, (z)-isomer
  • sulindacum
  • sulindacum
  • varnish
  • varnish
  • (z)-5-fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1h-indene-3-acetic acid
  • (z)-5-fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1h-indene-3-acetic acid

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT04823052Phase 2Jan 31, 2022Healx Limited, Rush University
NCT04542135Phase 2Nov 20, 2020Stony Brook University
NCT04207944Phase 2Jan 31, 2020Duke University, Harvard University, Johns Hopkins University, Memorial Sloan-Kettering Cancer Center, National Cancer Institute (NCI)
NCT02912741Phase 2Jan 1, 2017Cairo University
NCT02645617Phase 1Jun 1, 2016Advantage Dental
NCT01636128Phase 2Mar 1, 2014Cancer Prevention Pharmaceuticals, Inc., University of Arizona
NCT01843179Phase 2Jan 1, 2014Harvard University
NCT01483144Phase 3Oct 1, 2013Cancer Prevention Pharmaceuticals, Inc., University of Hamburg, University of Rochester
NCT01856322Phase 2Apr 1, 2013Humboldt University, National Cancer Institute (NCI), National Institutes of Health (NIH)
NCT01349881Phase 3Mar 1, 2013Cancer Prevention Pharmaceuticals, Inc., National Cancer Institute (NCI), Southwest Oncology Group, University of California, Irvine
NCT01761877Phase 2Dec 1, 2012Stony Brook University, University of Arizona
NCT01245816Phase 3Mar 1, 2011Cancer Prevention Pharmaceuticals, Inc.
NCT01187901Phase 2Apr 1, 2010National Cancer Institute (NCI), University of Utah
NCT00841204Phase 2Feb 1, 2009National Cancer Institute (NCI), University of Arizona
NCT00755976Phase 2Aug 1, 2007Cancer Trials Ireland
NCT00392665Phase 2Oct 1, 2006Emory University, Genentech, Harvard University, OSI Pharmaceuticals, University of North Carolina at Chapel Hill
NCT00368927Phase 2Aug 1, 2006Mayo Clinic, National Cancer Institute (NCI)
NCT00343629N/AApr 1, 2006Mayo Clinic, National Cancer Institute (NCI)
NCT00319007Phase 2Apr 1, 2006Dutch Cancer Society, Radboud University
NCT00335504Phase 2Mar 1, 2006Mayo Clinic, National Cancer Institute (NCI)
Showing 20 of 40 trials
Page 1 / 2

Organizations

Research & Development (42)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government201041996
Mayo ClinicAcademic/Hospital6322002
OSI PharmaceuticalsFor profit6032001
Cancer Prevention Pharmaceuticals, Inc.For profit4322011
University of ArizonaAcademic/Hospital4022005
Harvard UniversityAcademic/Hospital3212006
AstellasFor profit2222001
Rutgers UniversityAcademic/Hospital2011996
Stony Brook UniversityAcademic/Hospital2212012
University of California, IrvineAcademic/Hospital2011998
University of Medicine and Dentistry of New JerseyAcademic/Hospital2211996
University of Texas at HoustonAcademic/Hospital2212001
University of UtahAcademic/Hospital2221999
Advantage DentalAcademic/Hospital1112016
Amrita Institute of Medical SciencesAcademic/Hospital1012006
Cairo UniversityAcademic/Hospital1112017
Cancer Trials IrelandAcademic/Hospital1112007
Cornell UniversityAcademic/Hospital1112006
Duke UniversityAcademic/Hospital1112020
Dutch Cancer SocietyAcademic/Hospital1012006
42 organizations
Page 1 / 3

Marketing (13)

OrganizationOrg typeRelationshipDate
Ani PharmaceuticalsFor profitMKTGFeb 28, 1992
Ani PharmaceuticalsFor profitSYNFeb 28, 1992
Chartwell PharmaceuticalsFor profitMKTGAug 30, 1991
Epic Pharma LlcFor profitSYNMar 25, 1991
Epic Pharma LlcFor profitMKTGSep 6, 1991
FosunFor profitMKTGAug 30, 1991
MerckFor profitSYNSep 27, 1978
MerckFor profitNDASep 27, 1978
MylanFor profitMKTGJun 22, 1993
Radius HealthFor profitMKTGSep 6, 1991
Rising PharmaceuticalsFor profitMKTGJun 22, 1993
Sun PharmaceuticalsFor profitMKTGApr 17, 1991
Watson PharmaceuticalsFor profitMKTGMar 3, 1988