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 |
|||
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 |
---|---|---|
Drug-associated cholelithiasis: a case of sulindac stone formation and the incorporation of sulindac metabolites into the gallstones. | 1999 Aug |
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Sulindac inhibits activation of the NF-kappaB pathway. | 1999 Sep 17 |
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Rat colorectal tumours treated with a range of non-steroidal anti-inflammatory drugs show altered cyclooxygenase-2 and cyclooxygenase-1 splice variant mRNA expression levels. | 2001 Jun |
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Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression. | 2001 Jun 15 |
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Regulation of renal proximal tubular epithelial cell hyaluronan generation: implications for diabetic nephropathy. | 2001 May |
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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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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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Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays. | 2002 Oct 29 |
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Altered expression of c-myc, p16 and p27 in rat colon tumors and its reversal by short-term treatment with chemopreventive agents. | 2002 Sep |
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Suppression of tumorigenesis in the Apc(min) mouse: down-regulation of beta-catenin signaling by a combination of tea plus sulindac. | 2003 Feb |
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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 Feb-Mar |
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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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Combination of tumor necrosis factor-alpha with sulindac augments its apoptotic potential and suppresses tumor growth of human carcinoma cells in nude mice. | 2003 Mar 15 |
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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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Drug-induced liver injury. | 2004 Mar 1 |
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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 Apr |
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Endothelial survival factors and spatial completion, but not pericyte coverage of retinal capillaries determine vessel plasticity. | 2005 Dec |
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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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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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Sulindac enhances the proteasome inhibitor bortezomib-mediated oxidative stress and anticancer activity. | 2005 Jul 15 |
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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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Sulindac induces apoptosis and protects against colon carcinoma in mice. | 2005 May 14 |
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Sulindac activates nuclear translocation of AIF, DFF40 and endonuclease G but not induces oligonucleosomal DNA fragmentation in HT-29 cells. | 2005 Sep 2 |
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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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Induction of spermidine/spermine N1-acetyltransferase (SSAT) by aspirin in Caco-2 colon cancer cells. | 2006 Feb 15 |
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Cyclooxygenase-2 expression in hamster and human pancreatic neoplasia. | 2006 Jun |
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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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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 Jan |
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Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin. | 2007 Jan 31 |
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Sulindac induces specific degradation of the HPV oncoprotein E7 and causes growth arrest and apoptosis in cervical carcinoma cells. | 2007 Jan 8 |
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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FDA ORPHAN DRUG |
818421
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WHO-VATC |
QM01AB02
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NDF-RT |
N0000175721
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NDF-RT |
N0000000160
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EU-Orphan Drug |
EU/3/12/1086
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FDA ORPHAN DRUG |
752620
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9352
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757344
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184SNS8VUH
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SUB10744MIG
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DTXSID4023624
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SULINDAC
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5425
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1548887
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3791
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2534
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38194-50-2
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M10382
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C850
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Sulindac
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184SNS8VUH
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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)