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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=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-

HIDE SMILES / InChI

Description
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

Curator's Comment: Sulindac penetrates the blood-brain and placental barriers. Concentrations in brain did not exceed 4% of those in plasma.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

5.7326397E11
Primary
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

5.7326397E11
Primary
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

5.7326397E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
11.4 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2.95 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

PubMed

TitleDatePubMed
Drug-associated cholelithiasis: a case of sulindac stone formation and the incorporation of sulindac metabolites into the gallstones.
1999 Aug
Sulindac inhibits activation of the NF-kappaB pathway.
1999 Sep 17
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
Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression.
2001 Jun 15
Regulation of renal proximal tubular epithelial cell hyaluronan generation: implications for diabetic nephropathy.
2001 May
Chemoprevention of esophageal adenocarcinoma by COX-2 inhibitors in an animal model of Barrett's esophagus.
2002 Apr
Sulindac induces apoptosis, inhibits proliferation and activates caspase-3 in Hep G2 cells.
2002 Jan-Feb
Expression and regulation of nonsteroidal anti-inflammatory drug-activated gene (NAG-1) in human and mouse tissue.
2002 May
Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays.
2002 Oct 29
Altered expression of c-myc, p16 and p27 in rat colon tumors and its reversal by short-term treatment with chemopreventive agents.
2002 Sep
Suppression of tumorigenesis in the Apc(min) mouse: down-regulation of beta-catenin signaling by a combination of tea plus sulindac.
2003 Feb
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
ROCK and nuclear factor-kappaB-dependent activation of cyclooxygenase-2 by Rho GTPases: effects on tumor growth and therapeutic consequences.
2003 Jul
Regional response leading to tumorigenesis after sulindac in small and large intestine of mice with Apc mutations.
2003 Mar
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
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
Drug-induced liver injury.
2004 Mar 1
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
Endothelial survival factors and spatial completion, but not pericyte coverage of retinal capillaries determine vessel plasticity.
2005 Dec
Sulindac suppresses nuclear factor-kappaB activation and RANTES gene and protein expression in endometrial stromal cells from women with endometriosis.
2005 Dec
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
Sulindac enhances the proteasome inhibitor bortezomib-mediated oxidative stress and anticancer activity.
2005 Jul 15
Apoptosis of human gastric cancer SGC-7901 cells induced by mitomycin combined with sulindac.
2005 Mar 28
Sulindac induces apoptosis and protects against colon carcinoma in mice.
2005 May 14
Sulindac activates nuclear translocation of AIF, DFF40 and endonuclease G but not induces oligonucleosomal DNA fragmentation in HT-29 cells.
2005 Sep 2
Sulindac regulates the aryl hydrocarbon receptor-mediated expression of Phase 1 metabolic enzymes in vivo and in vitro.
2006 Aug
Induction of spermidine/spermine N1-acetyltransferase (SSAT) by aspirin in Caco-2 colon cancer cells.
2006 Feb 15
Cyclooxygenase-2 expression in hamster and human pancreatic neoplasia.
2006 Jun
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
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
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin.
2007 Jan 31
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
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
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
NSC-757344
Code English
Sulindac [WHO-DD]
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 MONOGRAPH]
Common Name English
SULINDAC [EP MONOGRAPH]
Common Name English
SULINDAC [MI]
Common Name English
CIS-5-FLUORO-2-METHYL-1-((P-METHYLSULFINYL)BENZYLIDENE)INDENE-3-ACETIC ACID
Common Name English
MK-231
Code English
SULINDAC [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
WHO-ATC M01AB02
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
NDF-RT N0000175722
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
FDA ORPHAN DRUG 619917
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
LIVERTOX NBK548315
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
FDA ORPHAN DRUG 387012
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
FDA ORPHAN DRUG 818421
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
WHO-VATC QM01AB02
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
NDF-RT N0000175721
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
NDF-RT N0000000160
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
EU-Orphan Drug EU/3/12/1086
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
FDA ORPHAN DRUG 752620
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
Code System Code Type Description
CHEBI
9352
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
NSC
757344
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
FDA UNII
184SNS8VUH
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
EVMPD
SUB10744MIG
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
EPA CompTox
DTXSID4023624
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
WIKIPEDIA
SULINDAC
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
IUPHAR
5425
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
PUBCHEM
1548887
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
INN
3791
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
DRUG CENTRAL
2534
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
CAS
38194-50-2
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
MERCK INDEX
M10382
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY Merck Index
NCI_THESAURUS
C850
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
LACTMED
Sulindac
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
DAILYMED
184SNS8VUH
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
RXCUI
10237
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY RxNorm
ChEMBL
CHEMBL15770
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
DRUG BANK
DB00605
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
RS_ITEM_NUM
1642008
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
ECHA (EC/EINECS)
253-819-2
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY
MESH
D013467
Created by admin on Sat Dec 17 02:19:23 UTC 2022 , Edited by admin on Sat Dec 17 02:19:23 UTC 2022
PRIMARY