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Details

Stereochemistry RACEMIC
Molecular Formula C20H17FO3S
Molecular Weight 356.4124
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SULINDAC

SMILES

CC/1=C(CC(=O)O)c2cc(ccc2\C1=C(\[H])/c3ccc(cc3)S(=O)C)F

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 356.4124
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: 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

573264000000
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

573264000000
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

573264000000
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
Sulindac and a cyclooxygenase-2 inhibitor, etodolac, increase APC mRNA in the colon of rats treated with azoxymethane.
2000 Dec
Growth, adipose, brain, and skin alterations resulting from targeted disruption of the mouse peroxisome proliferator-activated receptor beta(delta).
2000 Jul
p21(WAF1/cip1) is an important determinant of intestinal cell response to sulindac in vitro and in vivo.
2001 Aug 15
Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression.
2001 Jun 15
Cell cycle effects of nonsteroidal anti-inflammatory drugs and enhanced growth inhibition in combination with gemcitabine in pancreatic carcinoma cells.
2001 Sep
Dysregulation of integrin-linked kinase (ILK) signaling in colonic polyposis.
2001 Sep 27
Induction of multidrug resistance proteins MRP1 and MRP3 and gamma-glutamylcysteine synthetase gene expression by nonsteroidal anti-inflammatory drugs in human colon cancer cells.
2002 Feb 8
Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs.
2002 Nov
Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays.
2002 Oct 29
A mouse model of human oral-esophageal cancer.
2002 Sep
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
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
Genetic polymorphisms of human flavin monooxygenase 3 in sulindac-mediated primary chemoprevention of familial adenomatous polyposis.
2004 Dec 15
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
Nonsteroidal antiinflammatory drugs differentially suppress endometriosis in a murine model.
2005 Jan
Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes.
2005 Jul
Sulindac induces apoptosis and protects against colon carcinoma in mice.
2005 May 14
Induction of spermidine/spermine N1-acetyltransferase (SSAT) by aspirin in Caco-2 colon cancer cells.
2006 Feb 15
Non-steroidal anti-inflammatory agents, tolmetin and sulindac, inhibit liver tryptophan 2,3-dioxygenase activity and alter brain neurotransmitter levels.
2006 Nov 10
Sulindac, a nonsteroidal anti-inflammatory drug, selectively inhibits interferon-gamma-induced expression of the chemokine CXCL9 gene in mouse macrophages.
2006 Nov 17
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

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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:05:44 UTC 2021
Edited
by admin
on Fri Jun 25 21:05:44 UTC 2021
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
NSC-757344
Code 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 [WHO-DD]
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 Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
WHO-ATC M01AB02
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
NDF-RT N0000175722
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
FDA ORPHAN DRUG 619917
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
LIVERTOX 915
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
FDA ORPHAN DRUG 387012
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
FDA ORPHAN DRUG 818421
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
WHO-VATC QM01AB02
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
NDF-RT N0000175721
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
NDF-RT N0000000160
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
EU-Orphan Drug EU/3/12/1086
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
FDA ORPHAN DRUG 752620
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
Code System Code Type Description
FDA UNII
184SNS8VUH
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
EVMPD
SUB10744MIG
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
EPA CompTox
38194-50-2
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
WIKIPEDIA
SULINDAC
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
IUPHAR
5425
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
PUBCHEM
1548887
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
INN
3791
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
DRUG CENTRAL
2534
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
USP_CATALOG
1642008
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY USP-RS
CAS
38194-50-2
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
MERCK INDEX
M10382
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C850
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
LACTMED
Sulindac
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
RXCUI
10237
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL15770
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
DRUG BANK
DB00605
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
ECHA (EC/EINECS)
253-819-2
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
PRIMARY
MESH
D013467
Created by admin on Fri Jun 25 21:05:44 UTC 2021 , Edited by admin on Fri Jun 25 21:05:44 UTC 2021
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
METABOLIC ENZYME -> SUBSTRATE
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