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Identification
NameSulindac
Accession NumberDB00605  (APRD01243)
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
Synonyms
(Z)-5-Fluoro-2-methyl-1-((P-(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
Clinoril
Sulindac
Sulindaco
Sulindacum
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Clinoril Tab 150mgtablet150 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1979-12-311998-08-14Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Clinoril Tab 200mgtablet200 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1979-12-311998-08-14Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-sulindac Tab 150mgtablet150 mgoralNu Pharm Inc1994-12-312012-09-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Nu-sulindac Tab 200mgtablet200 mgoralNu Pharm Inc1994-12-312012-09-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penta-sulindactablet200 mgoralPentapharm Ltd.Not applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Penta-sulindactablet150 mgoralPentapharm Ltd.Not applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Sulindac-150 Tab 150mgtablet150 mgoralPro Doc Limitee1989-12-312009-07-23Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Sulindac-200 Tab 200mgtablet200 mgoralPro Doc Limitee1989-12-312009-07-23Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-sulindactablet150 mgoralTeva Canada Limited1988-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Teva-sulindactablet200 mgoralTeva Canada Limited1988-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-sulin Tab 150mgtablet150 mgoralApotex Inc1988-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Apo-sulin Tab 200mgtablet200 mgoralApotex Inc1988-12-31Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Sulindactablet150 mg/1oralMylan Pharmaceuticals Inc.1993-06-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralCarilion Materials Management1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralH.J. Harkins Company, Inc.1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralRichmond Pharmaceuticals2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralSTAT Rx USA LLC2010-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralEpic Pharma, LLC2015-07-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralbryant ranch prepack1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralMajor Pharmaceuticals2010-11-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralEpic Pharma, LLC2015-07-28Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralGolden State Medical Supply, Inc.2010-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralMajor Pharmaceuticals2010-11-30Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralEpic Pharma, LLC2010-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralGolden State Medical Supply, Inc.2010-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralMajor Pharmaceuticals2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralEpic Pharma, LLC2010-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralPd Rx Pharmaceuticals, Inc.1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralWatson Laboratories, Inc.1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralAidarex Pharmaceuticals LLC2010-01-25Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralPhysicians Total Care, Inc.2007-07-05Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralWatson Laboratories, Inc.1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralMutual Pharmaceutical Company, Inc.2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralHeritage Pharmaceuticals Inc.2007-07-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralPhysicians Total Care, Inc.2007-07-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralCarilion Materials Management1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralMylan Institutional Inc.1997-01-31Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralMylan Pharmaceuticals Inc.1993-06-22Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralMutual Pharmaceutical Company, Inc.2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralRichmond Pharmaceuticals2009-09-04Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralHeritage Pharmaceuticals Inc.2007-07-16Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet150 mg/1oralbryant ranch prepack1990-04-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Sulindactablet200 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-06-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
ClinorilMerck
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number38194-50-2
WeightAverage: 356.411
Monoisotopic: 356.088243305
Chemical FormulaC20H17FO3S
InChI KeyInChIKey=MLKXDPUZXIRXEP-MFOYZWKCSA-N
InChI
InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
IUPAC Name
2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
SMILES
CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indenes and isoindenes. These are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndenes and isoindenes
Sub ClassNot Available
Direct ParentIndenes and isoindenes
Alternative Parents
Substituents
  • Indene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Sulfoxide
  • Sulfinyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor acute or long-term use in the relief of signs and symptoms of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute painful shoulder (acute subacromial bursitis/supraspinatus tendinitis), and acute gouty arthritis.
PharmacodynamicsSulindac is a non-steroidal anti-inflammatory indene derivative, also possessing analgesic and antipyretic activities.
Mechanism of actionSulindac's exact mechanism of action is unknown. Its antiinflammatory effects are believed to be due to inhibition of both COX-1 and COX-2 which leads to the inhibition of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.
AbsorptionApproximately 90% absorbed in humans following oral administration.
Volume of distributionNot Available
Protein bindingAt 1 mcg/ml concentrations, approximately 93% sulindac and 98% of its sulfide metabolite are bound to human serum albumin.
Metabolism

Undergoes two major biotransformations: reversible reduction to the sulfide metabolite, and irreversible oxidation to the sulfone metabolite. Sulindac and its sulfide and sulfone metabolites undergo extensive enterohepatic circulation. Available evidence indicates that the biological activity resides with the sulfide metabolite. Side chain hydroxylation and hydration of the double bond also occur.

SubstrateEnzymesProduct
Sulindac
Not Available
Sulindac sulfideDetails
Sulindac
Not Available
Sulindac sulfoneDetails
Route of eliminationSulindac is excreted in rat milk; concentrations in milk were 10 to 20% of those levels in plasma. It is not known if sulindac is excreted in human milk. Approximately 50% of the administered dose of sulindac is excreted in the urine with the conjugated sulfone metabolite accounting for the major portion. Hepatic metabolism is an important elimination pathway.
Half lifeThe mean half-life of sulindac is 7.8 hours while the mean half-life of the sulfide metabolite is 16.4 hours.
Clearance
  • Renal cl=68.12 +/- 27.56 mL/min [NORMAL (19-41 yrs)]
ToxicityAcute oral toxicity (LD50) in rats is 264 mg/kg. Cases of overdose have been reported and rarely, deaths have occurred. The following signs and symptoms may be observed following overdose: stupor, coma, diminished urine output and hypotension.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier+0.8325
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5904
P-glycoprotein inhibitor INon-inhibitor0.5847
P-glycoprotein inhibitor IINon-inhibitor0.9949
Renal organic cation transporterNon-inhibitor0.8753
CYP450 2C9 substrateNon-substrate0.7715
CYP450 2D6 substrateNon-substrate0.8961
CYP450 3A4 substrateNon-substrate0.5629
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5789
Ames testNon AMES toxic0.5451
CarcinogenicityNon-carcinogens0.6516
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0989 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9768
hERG inhibition (predictor II)Non-inhibitor0.8671
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Merck research laboratories div merck co inc
  • Epic pharma llc
  • Heritage pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral150 mg
Tabletoral200 mg
Tabletoral150 mg/1
Tabletoral200 mg/1
Prices
Unit descriptionCostUnit
Sulindac powder17.36USD g
Clinoril 200 mg tablet1.58USD tablet
Sulindac 200 mg tablet1.23USD tablet
Sulindac 150 mg tablet1.0USD tablet
Apo-Sulin 200 mg Tablet0.51USD tablet
Novo-Sundac 200 mg Tablet0.51USD tablet
Nu-Sulindac 200 mg Tablet0.51USD tablet
Apo-Sulin 150 mg Tablet0.4USD tablet
Novo-Sundac 150 mg Tablet0.4USD tablet
Nu-Sulindac 150 mg Tablet0.4USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point183 °CPhysProp
water solubility3000 mg/LMERCK INDEX (1996); pH 7
logP3.42SANGSTER (1993)
pKa4.7MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.0251 mg/mLALOGPS
logP2.96ALOGPS
logP2.93ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.56 m3·mol-1ChemAxon
Polarizability37.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Gary Piazza, Robert Reynolds, “Derivatives of sulindac, use thereof and preparation thereof.” U.S. Patent US20070244122, issued October 18, 2007.

US20070244122
General ReferencesNot Available
External Links
ATC CodesM01AB02
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelDownload (106 KB)
MSDSDownload (73.2 KB)
Interactions
Drug Interactions
Drug
AbciximabSulindac may increase the anticoagulant activities of Abciximab.
AcenocoumarolSulindac may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Sulindac is combined with Acetylsalicylic acid.
AliskirenSulindac may decrease the antihypertensive activities of Aliskiren.
AlteplaseSulindac may increase the anticoagulant activities of Alteplase.
AmikacinSulindac may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAmitriptyline may increase the antiplatelet activities of Sulindac.
AnistreplaseSulindac may increase the anticoagulant activities of Anistreplase.
ApixabanThe risk or severity of adverse effects can be increased when Sulindac is combined with Apixaban.
ArbekacinSulindac may decrease the excretion rate of Arbekacin which could result in a lower serum level and potentially a reduction in efficacy.
BalsalazideSulindac may increase the nephrotoxic activities of Balsalazide.
Citric AcidSulindac may increase the anticoagulant activities of Citric Acid.
ColesevelamColesevelam can cause a decrease in the absorption of Sulindac resulting in a reduced serum concentration and potentially a decrease in efficacy.
CollagenaseThe risk or severity of adverse effects can be increased when Sulindac is combined with Collagenase.
CyclosporineSulindac may increase the nephrotoxic activities of Cyclosporine.
Dabigatran etexilateSulindac may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinSulindac may increase the anticoagulant activities of Dalteparin.
DasatinibDasatinib may increase the anticoagulant activities of Sulindac.
DeferasiroxThe risk or severity of adverse effects can be increased when Sulindac is combined with Deferasirox.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Sulindac is combined with Deoxycholic Acid.
DesmopressinThe risk or severity of adverse effects can be increased when Sulindac is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Sulindac.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Sulindac.
DicoumarolSulindac may increase the anticoagulant activities of Dicoumarol.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Sulindac.
Dimethyl sulfoxideThe metabolism of Sulindac can be decreased when combined with Dimethyl sulfoxide.
DrospirenoneSulindac may increase the hyperkalemic activities of Drospirenone.
Edetic AcidSulindac may increase the anticoagulant activities of Edetic Acid.
EnoxaparinSulindac may increase the anticoagulant activities of Enoxaparin.
EplerenoneSulindac may decrease the antihypertensive activities of Eplerenone.
Ethyl biscoumacetateSulindac may increase the anticoagulant activities of Ethyl biscoumacetate.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Sulindac.
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Sulindac.
Fondaparinux sodiumSulindac may increase the anticoagulant activities of Fondaparinux sodium.
FramycetinSulindac may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
GentamicinSulindac may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
GlucosamineGlucosamine may increase the antiplatelet activities of Sulindac.
HaloperidolThe risk or severity of adverse effects can be increased when Sulindac is combined with Haloperidol.
HeparinSulindac may increase the anticoagulant activities of Heparin.
HomoharringtonineThe risk or severity of adverse effects can be increased when Sulindac is combined with Homoharringtonine.
HydralazineSulindac may decrease the antihypertensive activities of Hydralazine.
IbritumomabThe risk or severity of adverse effects can be increased when Sulindac is combined with Ibritumomab.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sulindac.
IcosapentThe risk or severity of adverse effects can be increased when Sulindac is combined with Icosapent.
InfliximabThe risk or severity of adverse effects can be increased when Infliximab is combined with Sulindac.
KanamycinSulindac may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Sulindac.
LimaprostLimaprost may increase the antiplatelet activities of Sulindac.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Sulindac.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Sulindac.
NadololSulindac may decrease the antihypertensive activities of Nadolol.
NeomycinSulindac may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NetilmicinSulindac may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
ObinutuzumabThe risk or severity of adverse effects can be increased when Sulindac is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Sulindac.
PamidronateThe risk or severity of adverse effects can be increased when Sulindac is combined with Pamidronate.
ParoxetineParoxetine may increase the antiplatelet activities of Sulindac.
PemetrexedThe serum concentration of Pemetrexed can be increased when it is combined with Sulindac.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Sulindac.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Sulindac.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Sulindac.
PhenindioneSulindac may increase the anticoagulant activities of Phenindione.
PhenprocoumonSulindac may increase the anticoagulant activities of Phenprocoumon.
PorfimerSulindac may increase the photosensitizing activities of Porfimer.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Sulindac.
ProbenecidThe serum concentration of Sulindac can be increased when it is combined with Probenecid.
ReteplaseSulindac may increase the anticoagulant activities of Reteplase.
RibostamycinSulindac may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RidogrelSulindac may increase the anticoagulant activities of Ridogrel.
RivaroxabanSulindac may increase the anticoagulant activities of Rivaroxaban.
Salicylate-sodiumThe risk or severity of adverse effects can be increased when Sulindac is combined with Salicylate-sodium.
SparfloxacinSulindac may increase the neuroexcitatory activities of Sparfloxacin.
SpectinomycinSulindac may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptokinaseSulindac may increase the anticoagulant activities of Streptokinase.
StreptomycinSulindac may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
SulodexideSulindac may increase the anticoagulant activities of Sulodexide.
TacrolimusSulindac may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Sulindac.
TenecteplaseSulindac may increase the anticoagulant activities of Tenecteplase.
TenofovirThe risk or severity of adverse effects can be increased when Sulindac is combined with Tenofovir.
TipranavirTipranavir may increase the antiplatelet activities of Sulindac.
TobramycinSulindac may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideSulindac may decrease the diuretic activities of Torasemide.
TositumomabThe risk or severity of adverse effects can be increased when Sulindac is combined with Tositumomab.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Sulindac.
TriamtereneSulindac may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Sulindac.
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Sulindac.
UrokinaseSulindac may increase the anticoagulant activities of Urokinase.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Sulindac.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Sulindac.
VenlafaxineVenlafaxine may increase the antiplatelet activities of Sulindac.
VerteporfinSulindac may increase the photosensitizing activities of Verteporfin.
Vitamin EVitamin E may increase the antiplatelet activities of Sulindac.
WarfarinSulindac may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

1. Prostaglandin G/H synthase 2

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 2 P35354 Details

References:

  1. Giuliano F, Warner TD: Ex vivo assay to determine the cyclooxygenase selectivity of non-steroidal anti-inflammatory drugs. Br J Pharmacol. 1999 Apr;126(8):1824-30. Pubmed
  2. Molina MA, Sitja-Arnau M, Lemoine MG, Frazier ML, Sinicrope FA: Increased cyclooxygenase-2 expression in human pancreatic carcinomas and cell lines: growth inhibition by nonsteroidal anti-inflammatory drugs. Cancer Res. 1999 Sep 1;59(17):4356-62. Pubmed
  3. Yip-Schneider MT, Barnard DS, Billings SD, Cheng L, Heilman DK, Lin A, Marshall SJ, Crowell PL, Marshall MS, Sweeney CJ: Cyclooxygenase-2 expression in human pancreatic adenocarcinomas. Carcinogenesis. 2000 Feb;21(2):139-46. Pubmed
  4. Fosslien E: Biochemistry of cyclooxygenase (COX)-2 inhibitors and molecular pathology of COX-2 in neoplasia. Crit Rev Clin Lab Sci. 2000 Oct;37(5):431-502. Pubmed
  5. Taylor MT, Lawson KR, Ignatenko NA, Marek SE, Stringer DE, Skovan BA, Gerner EW: Sulindac sulfone inhibits K-ras-dependent cyclooxygenase-2 expression in human colon cancer cells. Cancer Res. 2000 Dec 1;60(23):6607-10. Pubmed

2. Prostaglandin G/H synthase 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Giuliano F, Warner TD: Ex vivo assay to determine the cyclooxygenase selectivity of non-steroidal anti-inflammatory drugs. Br J Pharmacol. 1999 Apr;126(8):1824-30. Pubmed
  2. Lim JT, Piazza GA, Han EK, Delohery TM, Li H, Finn TS, Buttyan R, Yamamoto H, Sperl GJ, Brendel K, Gross PH, Pamukcu R, Weinstein IB: Sulindac derivatives inhibit growth and induce apoptosis in human prostate cancer cell lines. Biochem Pharmacol. 1999 Oct 1;58(7):1097-107. Pubmed
  3. Soriano AF, Helfrich B, Chan DC, Heasley LE, Bunn PA Jr, Chou TC: Synergistic effects of new chemopreventive agents and conventional cytotoxic agents against human lung cancer cell lines. Cancer Res. 1999 Dec 15;59(24):6178-84. Pubmed
  4. Cheng ZJ, Tikkanen I, Vapaatalo H, Mervaala EM: Vascular effects of COX inhibition and AT1 receptor blockade in transgenic rats harboring mouse renin-2 gene. J Physiol Pharmacol. 2002 Dec;53(4 Pt 1):597-613. Pubmed
  5. Cheng ZJ, Finckenberg P, Louhelainen M, Merasto S, Tikkanen I, Vapaatalo H, Mervaala EM: Cardiovascular and renal effects of cyclooxygenase inhibition in transgenic rats harboring mouse renin-2 gene (TGR[mREN2]27). Eur J Pharmacol. 2003 Feb 14;461(2-3):159-69. Pubmed

3. Aldose reductase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Aldose reductase P15121 Details

References:

  1. Sharma YR, Vajpayee RB, Bhatnagar R, Mohan M, Azad RV, Kumar M, Nath R: Topical sulindac therapy in diabetic senile cataracts: cataract-IV. Indian J Ophthalmol. 1989 Jul-Sep;37(3):127-33. Pubmed
  2. Crabbe MJ, Freeman G, Halder AB, Bron AJ: The inhibition of bovine lens aldose reductase by Clinoril, its absorption into the human red cell and its effect on human red cell aldose reductase activity. Ophthalmic Res. 1985;17(2):85-9. Pubmed
  3. Chaudhry PS, Cabrera J, Juliani HR, Varma SD: Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin. Biochem Pharmacol. 1983 Jul 1;32(13):1995-8. Pubmed
  4. Jacobson M, Sharma YR, Cotlier E, Hollander JD: Diabetic complications in lens and nerve and their prevention by sulindac or sorbinil: two novel aldose reductase inhibitors. Invest Ophthalmol Vis Sci. 1983 Oct;24(10):1426-9. Pubmed
  5. van der Sloot P, Mizisin A, Zochodne D: Sulindac in established experimental diabetes: a follow-up study. Can J Neurol Sci. 1995 Aug;22(3):198-201. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

4. Mitogen-activated protein kinase 3

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Mitogen-activated protein kinase 3 P27361 Details

References:

  1. Rice PL, Goldberg RJ, Ray EC, Driggers LJ, Ahnen DJ: Inhibition of extracellular signal-regulated kinase 1/2 phosphorylation and induction of apoptosis by sulindac metabolites. Cancer Res. 2001 Feb 15;61(4):1541-7. Pubmed
  2. Rice PL, Washington M, Schleman S, Beard KS, Driggers LJ, Ahnen DJ: Sulindac sulfide inhibits epidermal growth factor-induced phosphorylation of extracellular-regulated kinase 1/2 and Bad in human colon cancer cells. Cancer Res. 2003 Feb 1;63(3):616-20. Pubmed
  3. Rice PL, Beard KS, Driggers LJ, Ahnen DJ: Inhibition of extracellular-signal regulated kinases 1/2 is required for apoptosis of human colon cancer cells in vitro by sulindac metabolites. Cancer Res. 2004 Nov 15;64(22):8148-51. Pubmed
  4. Pangburn HA, Kraus H, Ahnen DJ, Rice PL: Sulindac metabolites inhibit epidermal growth factor receptor activation and expression. J Carcinog. 2005 Sep 2;4:16. Pubmed
  5. Rice PL, Peters SL, Beard KS, Ahnen DJ: Sulindac independently modulates extracellular signal-regulated kinase 1/2 and cyclic GMP-dependent protein kinase signaling pathways. Mol Cancer Ther. 2006 Mar;5(3):746-54. Pubmed

5. Peroxisome proliferator-activated receptor delta

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: negative modulator

Components

Name UniProt ID Details
Peroxisome proliferator-activated receptor delta Q03181 Details

References:

  1. He TC, Chan TA, Vogelstein B, Kinzler KW: PPARdelta is an APC-regulated target of nonsteroidal anti-inflammatory drugs. Cell. 1999 Oct 29;99(3):335-45. Pubmed
  2. Babbar N, Ignatenko NA, Casero RA Jr, Gerner EW: Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer. J Biol Chem. 2003 Nov 28;278(48):47762-75. Epub 2003 Sep 23. Pubmed
  3. Jarvis MC, Gray TJ, Palmer CN: Both PPARgamma and PPARdelta influence sulindac sulfide-mediated p21WAF1/CIP1 upregulation in a human prostate epithelial cell line. Oncogene. 2005 Dec 8;24(55):8211-5. Pubmed
  4. Kim DJ, Prabhu KS, Gonzalez FJ, Peters JM: Inhibition of chemically induced skin carcinogenesis by sulindac is independent of peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta). Carcinogenesis. 2006 May;27(5):1105-12. Epub 2006 Jan 16. Pubmed
  5. Liou JY, Ghelani D, Yeh S, Wu KK: Nonsteroidal anti-inflammatory drugs induce colorectal cancer cell apoptosis by suppressing 14-3-3epsilon. Cancer Res. 2007 Apr 1;67(7):3185-91. Pubmed

6. Prostaglandin D2 receptor 2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Prostaglandin D2 receptor 2 Q9Y5Y4 Details

References:

  1. Hata AN, Lybrand TP, Marnett LJ, Breyer RM: Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. Mol Pharmacol. 2005 Mar;67(3):640-7. Epub 2004 Nov 24. Pubmed

Enzymes

1. Cytochrome P450 1A1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A2

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Carriers

1. Serum albumin

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Russeva VN, Zhivkova ZD: Molecular basis of sulindac competition with specific markers for the major binding sites on human serum albumin. Arzneimittelforschung. 2003;53(3):174-81. Pubmed
  2. Shams-Eldeen MA, Vallner JJ, Needham TE: Interaction of sulindac and metabolite with human serum albumin. J Pharm Sci. 1978 Aug;67(8):1077-80. Pubmed
  3. Zhivkova ZD, Russeva VN: Thermodynamic characterization of the binding process of sulindac to human serum albumin. Arzneimittelforschung. 2003;53(1):53-6. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11