ChemFOnt: Showing chemical card for Sulindac (CFc000009091)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:07 UTC

Chemfont ID

CFc000009091

Molecule Identification

Common Name

Sulindac

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid	ChEBI
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid	ChEBI
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid	ChEBI
Clinoril	ChEBI
Sulindaco	ChEBI
Sulindacum	ChEBI
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid	Generator
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1H-indene-3-acetic acid	Generator
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((p-methylsulphinyl)benzylidene)indene-3-acetate	Generator
cis-5-Fluoro-2-methyl-1-((p-methylsulphinyl)benzylidene)indene-3-acetic acid	Generator
Aclin	HMDB
Arthrobid	HMDB
Cahill may roberts brand OF sulindac	HMDB
Chemia brand OF sulindac	HMDB
Copal	HMDB
Novo-sundac	HMDB
Nu pharm brand OF sulindac	HMDB
Sulindal	HMDB
Apo-sulin	HMDB
Kendrick brand OF sulindac	HMDB
Merck sharp and dohme brand OF sulindac	HMDB
Apotex brand OF sulindac	HMDB
Arthrocine	HMDB
Chibret	HMDB
Kenalin	HMDB
Klinoril	HMDB
Novo sundac	HMDB
Novopharm brand OF sulindac	HMDB
Alphapharm brand OF sulindac	HMDB
Apo sulin	HMDB
Merck brand OF sulindac	HMDB
Nu sulindac	HMDB
Nu-pharm brand OF sulindac	HMDB
Nu-sulindac	HMDB

Chemical Formula

C₂₀H₁₇FO₃S

Average Molecular Weight

356.411

Monoisotopic Molecular Weight

356.088243305

IUPAC Name

2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid

Traditional Name

sulindac

CAS Registry Number

38194-50-2

SMILES

CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(C=C1)S(C)=O

InChI Identifier

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-

InChI Key

MLKXDPUZXIRXEP-MFOYZWKCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indenes and isoindenes. Indenes and isoindenes are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indenes and isoindenes

Sub Class

Not Available

Direct Parent

Indenes and isoindenes

Alternative Parents

Substituents

Phenyl sulfoxide
Indene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Sulfoxide
Sulfinyl compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organohalogen compound
Organofluoride
Organooxygen compound
Organosulfur compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

organofluorine compound (CHEBI:9352 )
monocarboxylic acid (CHEBI:9352 )
sulfoxide (CHEBI:9352 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014743)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Sulindac Action Pathway (PathBank: SMP0000094)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	2.96	ALOGPS
logP	2.93	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.56 m³·mol⁻¹	ChemAxon
Polarizability	37.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon