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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 of SULINDAC

SMILES

C[S+]([O-])C1=CC=C(\C=C2\C(C)=C(CC(O)=O)C3=CC(F)=CC=C23)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-

HIDE SMILES / InChI

Molecular Formula C20H17FO3S
Molecular Weight 356.411
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Relationship of beta-catenin and Bcl-2 expression to sulindac-induced regression of intestinal tumors in Min mice.
1999 Apr
Evaluation of 5-aminosalicylic acid (5-ASA) for cancer chemoprevention: lack of efficacy against nascent adenomatous polyps in the Apc(Min) mouse.
1999 Apr
Drug-associated cholelithiasis: a case of sulindac stone formation and the incorporation of sulindac metabolites into the gallstones.
1999 Aug
Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes.
1999 May
Non-steroidal anti-inflammatory drugs with different cyclooxygenase inhibitory profiles that prevent aberrant crypt foci formation but vary in acute gastrotoxicity in a rat model.
2000 Dec
Sulindac and a cyclooxygenase-2 inhibitor, etodolac, increase APC mRNA in the colon of rats treated with azoxymethane.
2000 Dec
Role of BAX in the apoptotic response to anticancer agents.
2000 Nov 3
Relationship between APC genotype, polyp distribution, and oral sulindac treatment in the colon and rectum of patients with familial adenomatous polyposis.
2001 Aug
Molecular analysis of sulindac-resistant adenomas in familial adenomatous polyposis.
2001 Dec
Chromatin-specific regulation of LEF-1-beta-catenin transcription activation and inhibition in vitro.
2001 Dec 15
Protein phosphatase 2A interacts with and directly dephosphorylates RelA.
2001 Dec 21
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
Regulation of renal proximal tubular epithelial cell hyaluronan generation: implications for diabetic nephropathy.
2001 May
Dysregulation of integrin-linked kinase (ILK) signaling in colonic polyposis.
2001 Sep 27
Effects of long-term administration of sulindac on APC mRNA and apoptosis in colons of rats treated with azoxymethane.
2002 Nov
Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs.
2002 Nov
Novel detection and differential utilization of a c-myc transcriptional block in colon cancer chemoprevention.
2002 Nov 1
Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays.
2002 Oct 29
Response of Apc(min) and A33 (delta N beta-cat) mutant mice to treatment with tea, sulindac, and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP).
2002 Sep 30
Rofecoxib (Vioxx), a specific cyclooxygenase-2 inhibitor, is chemopreventive in a mouse model of colon cancer.
2003 Aug
Regional response leading to tumorigenesis after sulindac in small and large intestine of mice with Apc mutations.
2003 Mar
Cyclooxygenase-independent induction of apoptosis by sulindac sulfone is mediated by polyamines in colon cancer.
2003 Nov 28
Prevention of retinal capillary basement membrane thickening in diabetic dogs by a non-steroidal anti-inflammatory drug.
2003 Sep
Death receptor regulation and celecoxib-induced apoptosis in human lung cancer cells.
2004 Dec 1
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 Dec 9
Photoprotective effects of sulindac against ultraviolet B-induced phototoxicity in the skin of SKH-1 hairless mice.
2004 Mar 15
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
Sulindac suppresses nuclear factor-kappaB activation and RANTES gene and protein expression in endometrial stromal cells from women with endometriosis.
2005 Dec
Sulindac enhances adenoviral vector expressing mda-7/IL-24-mediated apoptosis in human lung cancer.
2005 Feb
Nonsteroidal antiinflammatory drugs differentially suppress endometriosis in a murine model.
2005 Jan
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
Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes.
2005 Jul
Methylation in the p21WAF1/cip1 promoter of Apc+/-, p21+/- mice and lack of response to sulindac.
2005 Mar 17
Apoptosis of human gastric cancer SGC-7901 cells induced by mitomycin combined with sulindac.
2005 Mar 28
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.
2006 Aug
Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents.
2006 Oct
Sulindac-derived reactive oxygen species induce apoptosis of human multiple myeloma cells via p38 mitogen activated protein kinase-induced mitochondrial dysfunction.
2007 Jan
Identification and functional analysis of common human flavin-containing monooxygenase 3 genetic variants.
2007 Jan
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin.
2007 Jan 31
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

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 Oct 21 20:32:42 UTC 2019
Edited
by admin
on Mon Oct 21 20:32:42 UTC 2019
Record UNII
184SNS8VUH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULINDAC
EP   INCI   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   INCI   USAN  
Official Name English
SULINDAC [ORANGE BOOK]
Common Name English
ARTRIBID
Brand Name English
CLINORIL
Brand Name English
SULINDAC [INN]
Common Name English
SULINDAC [JAN]
Common Name English
SULINDAC [USAN]
Common Name English
1H-INDENE-3-ACETIC ACID, 5-FLUORO-2-METHYL-1-((4-(METHYLSULFINYL)PHENYL)METHYLENE)-, (1Z)-
Common Name English
ARTHROCINE
Brand Name English
SULINDAC [USP-RS]
Common Name English
SULINDAC [INCI]
Common Name English
SULINDAC [MART.]
Common Name English
1H-INDENE-3-ACETIC ACID, 5-FLUORO-2-METHYL-1-((4-(METHYLSULFINYL)PHENYL)METHYLENE)-, (Z)-
Common Name English
SULINDAC [USP]
Common Name English
SULINDAC [WHO-DD]
Common Name English
SULINDAC [MI]
Common Name English
CIS-5-FLUORO-2-METHYL-1-((P-METHYLSULFINYL)BENZYLIDENE)INDENE-3-ACETIC ACID
Common Name English
SULINDAC [EP]
Common Name English
MK-231
Code English
SULINDAC [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
WHO-ATC M01AB02
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
NDF-RT N0000175722
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
FDA ORPHAN DRUG 619917
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
LIVERTOX 915
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
FDA ORPHAN DRUG 387012
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
WHO-VATC QM01AB02
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
NDF-RT N0000175721
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
NDF-RT N0000000160
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
EU-Orphan Drug EU/3/12/1086
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
Code System Code Type Description
EVMPD
SUB10744MIG
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
EPA CompTox
38194-50-2
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
WIKIPEDIA
SULINDAC
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
IUPHAR
5425
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
PUBCHEM
1548887
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
INN
3791
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
CAS
38194-50-2
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
MERCK INDEX
M10382
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C850
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
RXCUI
10237
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL15770
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
DRUG BANK
DB00605
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
ECHA (EC/EINECS)
253-819-2
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
MESH
D013467
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
LactMed
38194-50-2
Created by admin on Mon Oct 21 20:32:42 UTC 2019 , Edited by admin on Mon Oct 21 20:32:42 UTC 2019
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Available evidence indicates that the biological activity resides with the sulfide metabolite.
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC