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
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-MFOYZWKCSA-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-
DescriptionSources: http://www.drugbank.ca/drugs/DB00605Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/017911s073lbl.pdf
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
Sources: https://www.drugs.com/pro/sulindac.html
Curator's Comment: Sulindac penetrates the blood-brain and placental barriers. Concentrations in brain did not exceed 4% of those in plasma.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 |
0.02 µM [EC50] | ||
Target ID: CHEMBL1900 Sources: http://www.drugbank.ca/drugs/DB00605 |
0.36 µM [IC50] | ||
Target ID: CHEMBL5983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25532697 |
2.7 µM [IC50] | ||
Target ID: GO:0006927 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11854904 |
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Target ID: CHEMBL1743128 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17005917 |
2.11 µM [IC50] | ||
Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17005917 |
38.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SULINDAC Approved UseCLINORIL 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 Date5.7326397E11 |
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Primary | SULINDAC Approved UseCLINORIL 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 Date5.7326397E11 |
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Primary | SULINDAC Approved UseCLINORIL 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 Date5.7326397E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
9.21 μg/mL |
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40.8 μg × h/mL |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
7.8 h |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.9% |
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 |
PubMed
Title | Date | PubMed |
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Growth-suppressive effect of non-steroidal anti-inflammatory drugs on 11 colon-cancer cell lines and fluorescence differential display of genes whose expression is influenced by sulindac. | 2000 Dec 15 |
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Inhibition of rat colon tumors by sulindac and sulindac sulfone is independent of K-ras (codon 12) mutation. | 2000 Feb |
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Growth, adipose, brain, and skin alterations resulting from targeted disruption of the mouse peroxisome proliferator-activated receptor beta(delta). | 2000 Jul |
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15-LOX-1: a novel molecular target of nonsteroidal anti-inflammatory drug-induced apoptosis in colorectal cancer cells. | 2000 Jul 19 |
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Role of BAX in the apoptotic response to anticancer agents. | 2000 Nov 3 |
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Sulindac inhibited gene expression and activity of arylamine N-acetyltransferase and DNA-2-aminofluorene adduct formation in T24 human bladder tumor cells. | 2001 Dec |
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Enhanced apoptosis and transforming growth factor-beta1 expression in colorectal adenomas and carcinomas after Sulindac therapy. | 2001 Jul |
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Dysregulation of integrin-linked kinase (ILK) signaling in colonic polyposis. | 2001 Sep 27 |
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Chemoprevention of esophageal adenocarcinoma by COX-2 inhibitors in an animal model of Barrett's esophagus. | 2002 Apr |
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The influence of sulindac on patients with primary biliary cirrhosis that responds incompletely to ursodeoxycholic acid: a pilot study. | 2002 Dec |
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New indene-derivatives with anti-proliferative properties. | 2002 Feb 25 |
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Sulindac induces apoptosis, inhibits proliferation and activates caspase-3 in Hep G2 cells. | 2002 Jan-Feb |
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Expression and regulation of nonsteroidal anti-inflammatory drug-activated gene (NAG-1) in human and mouse tissue. | 2002 May |
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Effects of long-term administration of sulindac on APC mRNA and apoptosis in colons of rats treated with azoxymethane. | 2002 Nov |
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Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs. | 2002 Nov |
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Novel detection and differential utilization of a c-myc transcriptional block in colon cancer chemoprevention. | 2002 Nov 1 |
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Effect of sulindac treatment for attenuated familial adenomatous polyposis with a new germline APC mutation at codon 161: report of a case. | 2002 Oct |
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Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays. | 2002 Oct 29 |
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A mouse model of human oral-esophageal cancer. | 2002 Sep |
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Rofecoxib (Vioxx), a specific cyclooxygenase-2 inhibitor, is chemopreventive in a mouse model of colon cancer. | 2003 Aug |
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Sulindac sulfide inhibits epidermal growth factor-induced phosphorylation of extracellular-regulated kinase 1/2 and Bad in human colon cancer cells. | 2003 Feb 1 |
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Cardiovascular and renal effects of cyclooxygenase inhibition in transgenic rats harboring mouse renin-2 gene (TGR[mREN2]27). | 2003 Feb 14 |
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ROCK and nuclear factor-kappaB-dependent activation of cyclooxygenase-2 by Rho GTPases: effects on tumor growth and therapeutic consequences. | 2003 Jul |
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Regional response leading to tumorigenesis after sulindac in small and large intestine of mice with Apc mutations. | 2003 Mar |
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Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer. | 2003 Nov 28 |
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Prevention of retinal capillary basement membrane thickening in diabetic dogs by a non-steroidal anti-inflammatory drug. | 2003 Sep |
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Nutritional-pharmacological combinations--a novel approach to reducing colon cancer incidence. | 2004 Aug |
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Drug-induced liver injury. | 2004 Mar 1 |
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Sulindac suppresses nuclear factor-kappaB activation and RANTES gene and protein expression in endometrial stromal cells from women with endometriosis. | 2005 Dec |
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Nonsteroidal antiinflammatory drugs differentially suppress endometriosis in a murine model. | 2005 Jan |
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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 Jan |
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Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. | 2005 Jul |
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Apoptosis of human gastric cancer SGC-7901 cells induced by mitomycin combined with sulindac. | 2005 Mar 28 |
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p27kip1 in intestinal tumorigenesis and chemoprevention in the mouse. | 2005 Oct 15 |
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Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems. | 2006 Aug |
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Sulindac regulates the aryl hydrocarbon receptor-mediated expression of Phase 1 metabolic enzymes in vivo and in vitro. | 2006 Aug |
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Sulindac, a nonsteroidal anti-inflammatory drug, selectively inhibits interferon-gamma-induced expression of the chemokine CXCL9 gene in mouse macrophages. | 2006 Nov 17 |
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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 Sep |
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Sulindac-derived reactive oxygen species induce apoptosis of human multiple myeloma cells via p38 mitogen activated protein kinase-induced mitochondrial dysfunction. | 2007 Jan |
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Identification and functional analysis of common human flavin-containing monooxygenase 3 genetic variants. | 2007 Jan |
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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 Mar 20 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11854904
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
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NCI_THESAURUS |
C1323
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WHO-ATC |
M01AB02
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NDF-RT |
N0000175722
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FDA ORPHAN DRUG |
619917
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LIVERTOX |
NBK548315
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FDA ORPHAN DRUG |
387012
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818421
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WHO-VATC |
QM01AB02
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NDF-RT |
N0000175721
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N0000000160
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EU-Orphan Drug |
EU/3/12/1086
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FDA ORPHAN DRUG |
752620
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DTXSID4023624
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SULINDAC
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5425
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M10382
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C850
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Sulindac
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10237
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CHEMBL15770
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DB00605
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1642008
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253-819-2
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D013467
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PRODRUG)