CHEBI:9352 - sulindac

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ChEBI Name sulindac
ChEBI ID CHEBI:9352
Definition A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the para position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H17FO3S
Net Charge 0
Average Mass 356.41158
Monoisotopic Mass 356.088
InChI 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-
InChIKey MLKXDPUZXIRXEP-MFOYZWKCSA-N
SMILES CC1=C(CC(O)=O)c2cc(F)ccc2C\1=C/c1ccc(cc1)S(C)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
tocolytic agent
Any compound used to suppress premature labour and immature birth by suppressing uterine contractions.
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ChEBI Ontology
Outgoing sulindac (CHEBI:9352) has functional parent acetic acid (CHEBI:15366)
sulindac (CHEBI:9352) has role analgesic (CHEBI:35480)
sulindac (CHEBI:9352) has role antineoplastic agent (CHEBI:35610)
sulindac (CHEBI:9352) has role antipyretic (CHEBI:35493)
sulindac (CHEBI:9352) has role apoptosis inducer (CHEBI:68495)
sulindac (CHEBI:9352) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
sulindac (CHEBI:9352) has role non-narcotic analgesic (CHEBI:35481)
sulindac (CHEBI:9352) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
sulindac (CHEBI:9352) has role prodrug (CHEBI:50266)
sulindac (CHEBI:9352) has role tocolytic agent (CHEBI:66993)
sulindac (CHEBI:9352) is a monocarboxylic acid (CHEBI:25384)
sulindac (CHEBI:9352) is a organofluorine compound (CHEBI:37143)
sulindac (CHEBI:9352) is a sulfoxide (CHEBI:22063)
Incoming nitrosulindac (CHEBI:75321) has functional parent sulindac (CHEBI:9352)
sulindac sulfide (CHEBI:75408) has functional parent sulindac (CHEBI:9352)
sulindac sulfone (CHEBI:64212) has functional parent sulindac (CHEBI:9352)
IUPAC Name
{(1Z)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-inden-3-yl}acetic acid
INNs Sources
sulindac WHO MedNet
sulindac ChemIDplus
sulindaco ChemIDplus
Sulindacum ChemIDplus
Synonyms Sources
(Z)-5-Fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid ChemIDplus
cis-5-Fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1H-indene-3-acetic acid ChemIDplus
cis-5-Fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic acid ChemIDplus
Sulindac KEGG COMPOUND
Brand Name Source
Clinoril DrugBank
Database Links Databases
2534 DrugCentral
C01531 KEGG COMPOUND
D00120 KEGG DRUG
DB00605 DrugBank
DE2039426 Patent
HMDB0014743 HMDB
Sulindac Wikipedia
SUZ PDBeChem
US3654349 Patent
View more database links
Registry Numbers Types Sources
2951842 Beilstein Registry Number Beilstein
2951842 Reaxys Registry Number Reaxys
38194-50-2 CAS Registry Number NIST Chemistry WebBook
38194-50-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11569947 PubMed citation Europe PMC
11927004 PubMed citation Europe PMC
12406542 PubMed citation Europe PMC
15020200 PubMed citation Europe PMC
15123337 PubMed citation Europe PMC
19884509 PubMed citation Europe PMC
23689354 PubMed citation Europe PMC
23804703 PubMed citation Europe PMC
Last Modified
22 February 2017