SULINDAC, TRANS-

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H17FO3S
Molecular Weight	356.411
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[S+]([O-])C1=CC=C(\C=C2/C(C)=C(CC(O)=O)C3=C2C=CC(F)=C3)C=C1

InChI

InChIKey=MLKXDPUZXIRXEP-RQZCQDPDSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C20H17FO3S
Molecular Weight	356.411
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00605
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf	Inhibitor 8504	0.02 µM [EC50]
Aldose reductase 45 Target ID: CHEMBL1900 Sources: http://www.drugbank.ca/drugs/DB00605	Inhibitor 8504	0.36 µM [IC50]
Aldo-keto reductase family 1 member B10 7 Target ID: CHEMBL5983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25532697	Inhibitor 8504	2.7 µM [IC50]
transformed cell apoptotic process 104 Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11854904	Activator 1447
Multidrug resistance-associated protein 4 14 Target ID: CHEMBL1743128 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17005917	Inhibitor 8504	2.11 µM [IC50]
Canalicular multispecific organic anion transporter 1 21 Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17005917	Inhibitor 8504	38.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf	Primary	Approved 8583	SULINDAC Approved Use CLINORIL is indicated for acute or long-term use in the relief of signs and symptoms of the following: 1. Osteoarthritis 2. Rheumatoid arthritis** 3. Ankylosing spondylitis 4. Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis) 5. Acute gouty arthritis Launch Date 1988
Rheumatoid arthritis 320 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf	Primary	Approved 8583	SULINDAC Approved Use CLINORIL is indicated for acute or long-term use in the relief of signs and symptoms of the following: 1. Osteoarthritis 2. Rheumatoid arthritis** 3. Ankylosing spondylitis 4. Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis) 5. Acute gouty arthritis Launch Date 1988
Ankylosing spondylitis 33 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf	Primary	Approved 8583	SULINDAC Approved Use CLINORIL is indicated for acute or long-term use in the relief of signs and symptoms of the following: 1. Osteoarthritis 2. Rheumatoid arthritis** 3. Ankylosing spondylitis 4. Acute painful shoulder (Acute subacromial bursitis/supraspinatus tendinitis) 5. Acute gouty arthritis Launch Date 1988

C_max

Value	Dose	Analyte	Population
4.69 μg/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8.7 μg/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
5.02 μg/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
9.21 μg/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
11.4 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8366178	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Analyte	Population
15.4 μg × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
44.8 μg × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	400 mg 1 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
19 μg × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
40.8 μg × h/mL EXPERIMENT https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1038/clpt.1982.178	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s074lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SULINDAC plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.95 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8366178	300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered:		SULINDAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
6.9% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s074lbl.pdf	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		SULINDAC plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT4 150 OAT3 747 MRP4 290 OAT1 725 OAT2 153		CYP1A1 151 CYP1A2 832 CYP1B1 71

Drug as perpetrator

Target	Modality	Activity
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17005917/	yes [IC50 2.11 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 3.62 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 36.2 uM]
OAT2 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 440 uM]
OAT4 150	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12388633/	yes [IC50 617 uM]
CYP1A1 272	inducer 1966 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/ijc.23218	yes
CYP1A2 2333	inducer 1966 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/ijc.23218	yes
CYP1B1 93	inducer 1966 Sources: https://onlinelibrary.wiley.com/doi/full/10.1002/ijc.23218	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9352	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9352
ChemicalBook	CB3740374	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3740374
eMolecules	594347	https://www.emolecules.com/cgi-bin/more?vid=594347
MolPort	MolPort-003-666-287	https://www.molport.com/shop/molecule-link/MolPort-003-666-287
Selleck Chemicals	Sulindac(Clinoril)	http://www.selleckchem.com/products/Sulindac(Clinoril).html

PubMed

Title	Date	PubMed
Non-steroidal anti-inflammatory agents, tolmetin and sulindac attenuate quinolinic acid (QA)-induced oxidative stress in primary hippocampal neurons and reduce QA-induced spatial reference memory deficits in male Wistar rats.	2007-03-20	17266991
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin.	2007-01-31	17243824
Sulindac induces specific degradation of the HPV oncoprotein E7 and causes growth arrest and apoptosis in cervical carcinoma cells.	2007-01-08	16488075
Sulindac-derived reactive oxygen species induce apoptosis of human multiple myeloma cells via p38 mitogen activated protein kinase-induced mitochondrial dysfunction.	2007-01	17136320
Identification and functional analysis of common human flavin-containing monooxygenase 3 genetic variants.	2007-01	17050781
A phase I clinical and pharmacokinetic study of the multi-drug resistance protein-1 (MRP-1) inhibitor sulindac, in combination with epirubicin in patients with advanced cancer.	2007-01	16642371
Sulindac, a nonsteroidal anti-inflammatory drug, selectively inhibits interferon-gamma-induced expression of the chemokine CXCL9 gene in mouse macrophages.	2006-11-17	17010317
Non-steroidal anti-inflammatory agents, tolmetin and sulindac, inhibit liver tryptophan 2,3-dioxygenase activity and alter brain neurotransmitter levels.	2006-11-10	16952380
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.	2006-10	17073578
Non-steroidal anti-inflammatory agents, tolmetin and sulindac, attenuate oxidative stress in rat brain homogenate and reduce quinolinic acid-induced neurodegeneration in rat hippocampal neurons.	2006-09	16850258
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.	2006-08	16867024
Sulindac regulates the aryl hydrocarbon receptor-mediated expression of Phase 1 metabolic enzymes in vivo and in vitro.	2006-08	16531450
Cyclooxygenase-2 expression in hamster and human pancreatic neoplasia.	2006-06	16820089
Induction of spermidine/spermine N1-acetyltransferase (SSAT) by aspirin in Caco-2 colon cancer cells.	2006-02-15	16262603
Effect of the non-steroidal anti-inflammatory drug sulindac on colorectal adenomas of uncolectomized familial adenomatous polyposis.	2006-01	16460482
Differential gene expression of sulindac-treated human breast epithelial cells.	2005-12	16273229
Endothelial survival factors and spatial completion, but not pericyte coverage of retinal capillaries determine vessel plasticity.	2005-12	16215210
Sulindac suppresses nuclear factor-kappaB activation and RANTES gene and protein expression in endometrial stromal cells from women with endometriosis.	2005-12	16159934
p27kip1 in intestinal tumorigenesis and chemoprevention in the mouse.	2005-10-15	16230399
Sulindac activates nuclear translocation of AIF, DFF40 and endonuclease G but not induces oligonucleosomal DNA fragmentation in HT-29 cells.	2005-09-02	15946692
Delayed mechanism for induction of gamma-glutamylcysteine synthetase heavy subunit mRNA stability by oxidative stress involving p38 mitogen-activated protein kinase signaling.	2005-08-05	15946948
Sulindac enhances the proteasome inhibitor bortezomib-mediated oxidative stress and anticancer activity.	2005-07-15	16033843
Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes.	2005-07	15843492
Sulindac induces apoptosis and protects against colon carcinoma in mice.	2005-05-14	15884131
Integrative role of cPLA with COX-2 and the effect of non-steriodal anti-inflammatory drugs in a transgenic mouse model of amyotrophic lateral sclerosis.	2005-04	15816863
Apoptosis of human gastric cancer SGC-7901 cells induced by mitomycin combined with sulindac.	2005-03-28	15793875
Methylation in the p21WAF1/cip1 promoter of Apc+/-, p21+/- mice and lack of response to sulindac.	2005-03-17	15688007
Sulindac enhances adenoviral vector expressing mda-7/IL-24-mediated apoptosis in human lung cancer.	2005-02	15713900
Nonsteroidal antiinflammatory drugs differentially suppress endometriosis in a murine model.	2005-01	15652904
Lack of specific amyloid-beta(1-42) suppression by nonsteroidal anti-inflammatory drugs in young, plaque-free Tg2576 mice and in guinea pig neuronal cultures.	2005-01	15340006
Genetic polymorphisms of human flavin monooxygenase 3 in sulindac-mediated primary chemoprevention of familial adenomatous polyposis.	2004-12-15	15623613
Nonsteroidal anti-inflammatory agents differ in their ability to suppress NF-kappaB activation, inhibition of expression of cyclooxygenase-2 and cyclin D1, and abrogation of tumor cell proliferation.	2004-12-09	15489888
Death receptor regulation and celecoxib-induced apoptosis in human lung cancer cells.	2004-12-01	15572759
Non-steroidal anti-inflammatory drug activated gene (NAG-1) expression is closely related to death receptor-4 and -5 induction, which may explain sulindac sulfide induced gastric cancer cell apoptosis.	2004-10	15180942
Nutritional-pharmacological combinations--a novel approach to reducing colon cancer incidence.	2004-08	15309441
Induction of transcription by p21Waf1/Cip1/Sdi1: role of NFkappaB and effect of non-steroidal anti-inflammatory drugs.	2004-07	15190207
Photoprotective effects of sulindac against ultraviolet B-induced phototoxicity in the skin of SKH-1 hairless mice.	2004-03-15	15020200
Drug-induced liver injury.	2004-03-01	14986274
Sulindac improves memory and increases NMDA receptor subunits in aged Fischer 344 rats.	2004-03	15123337
High-dose tamoxifen and sulindac as first-line treatment for desmoid tumors.	2004-02-01	14745880
The chemopreventive agent sulindac attenuates expression of the antiapoptotic protein survivin in colorectal carcinoma cells.	2004-02	14610217
Nonsteroidal anti-inflammatory drugs inhibit growth of human neuroendocrine tumor cells via G1 cell-cycle arrest.	2003-12-10	14566837
Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer.	2003-11-28	14506281
Hepatocellular damage from non-steroidal anti-inflammatory drugs.	2003-11	14566034
Prevention of retinal capillary basement membrane thickening in diabetic dogs by a non-steroidal anti-inflammatory drug.	2003-09	12861449
Rofecoxib (Vioxx), a specific cyclooxygenase-2 inhibitor, is chemopreventive in a mouse model of colon cancer.	2003-08	12902858
ROCK and nuclear factor-kappaB-dependent activation of cyclooxygenase-2 by Rho GTPases: effects on tumor growth and therapeutic consequences.	2003-07	12857884
Combination of tumor necrosis factor-alpha with sulindac augments its apoptotic potential and suppresses tumor growth of human carcinoma cells in nude mice.	2003-03-15	12627504
New TNF-alpha releasing inhibitors as cancer preventive agents from traditional herbal medicine and combination cancer prevention study with EGCG and sulindac or tamoxifen.	2003-03-12	12628509
Regional response leading to tumorigenesis after sulindac in small and large intestine of mice with Apc mutations.	2003-03	12663524

Patents

Sample Use Guides

In Vivo Use Guide

CLINORIL (Sulindac) should be administered orally twice a day with food. The maximum dosage is 400 mg per day. Dosages above 400 mg per day are not recommended. In osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis, the recommended starting dosage is 150 mg twice a day. The dosage may be lowered or raised depending on the response.

Route of Administration: Oral

In Vitro Use Guide

After 24 hours incubation with sulindac at 2mmol/L and 4mmol/L, the level of COX-2 and Bcl-2 protein were lowered in MKN45, SMMC7721 and HepG(2) cells

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:47:38 GMT 2025` Edited by `admin` on `Mon Mar 31 21:47:38 GMT 2025`
Record UNII	5NVO8803F9
Record Status	`Validated (UNII)`
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Name

Type

Language

SULINDAC, TRANS-

Common Name

English

SULINDAC RELATED COMPOUND A

Preferred Name

English

SULINDAC IMPURITY A [EP IMPURITY]

Common Name

English

SULINDAC RELATED COMPOUND A [USP IMPURITY]

Common Name

English

SULINDAC RELATED COMPOUND A [USP-RS]

Common Name

English

(E)-(5-FLUORO-2-METHYL-1-(4-(METHYLSULFINYL)BENZYLIDENE)-1H-INDEN-3-YL)ACETIC ACID

Systematic Name

English

1H-INDENE-3-ACETIC ACID, 5-FLUORO-2-METHYL-1-((4-(METHYLSULFINYL)PHENYL)METHYLENE)-, (1E)-

Systematic Name

English

SULINDAC, TRANS-(±)-

Common Name

English

TRANS-SULINDAC

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID90860554