indometacin (CHEBI:49662)

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CHEBI:49662 - indometacin

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ChEBI Name	indometacin

ChEBI ID	CHEBI:49662

Definition	A member of the class of indole-3-acetic acids that is indole-3-acetic acid in which the indole ring is substituted at positions 1, 2 and 5 by p-chlorobenzoyl, methyl, and methoxy groups, respectively. A non-steroidal anti-inflammatory drug, it is used in the treatment of musculoskeletal and joint disorders including osteoarthritis, rheumatoid arthritis, gout, bursitis and tendinitis.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:49660, CHEBI:5918

Supplier Information	ChemicalBook:CB1923045, ZINC000002020190

Download	Molfile XML SDF

more structures >>

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Mrv0541 10101311063D

41 43 0 0 0 0 999 V2000

0.7970 0.7410 1.0600 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1490 0.3050 2.2290 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8840 -0.2920 3.2530 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2510 -0.4410 3.1140 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8890 -0.0090 1.9560 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1710 0.5770 0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0

4.3350 -1.0360 3.6770 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2720 0.6170 2.0480 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.4010 1.1940 0.8450 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0510 1.8070 -0.9850 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0940 0.9310 -2.1730 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4330 1.4580 -3.4210 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4730 0.6340 -4.5260 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1770 -0.7120 -4.4000 C 0 0 0 0 0 0 0 0 0 0 0 0

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-2.9560 -1.0260 2.7670 C 0 0 0 0 0 0 0 0 0 0 0 0

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2.9740 -1.0180 4.1110 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2170 3.0050 -1.1070 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.5120 -1.7070 1.8740 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.9630 -1.4880 3.5260 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2290 -1.7430 -5.7960 Cl 0 0 0 0 0 0 0 0 0 0 0 0

0.3890 -0.6330 4.1500 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9570 -0.1340 1.8550 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6760 0.9100 0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0

4.9570 -1.4920 4.4470 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4150 -1.6140 2.7560 H 0 0 0 0 0 0 0 0 0 0 0 0

4.6720 -0.0150 3.4950 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6640 2.5080 -3.5200 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7340 1.0410 -5.4920 H 0 0 0 0 0 0 0 0 0 0 0 0

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-3.1600 0.8700 -0.3190 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3710 1.9870 1.0500 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5040 2.5230 -0.4080 H 0 0 0 0 0 0 0 0 0 0 0 0

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11 16 4 0 0 0 0

12 13 4 0 0 0 0

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13 14 4 0 0 0 0

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15 16 4 0 0 0 0

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16 35 1 0 0 0 0

17 36 1 0 0 0 0

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17 38 1 0 0 0 0

18 19 1 0 0 0 0

18 39 1 0 0 0 0

18 40 1 0 0 0 0

19 23 2 0 0 0 0

19 24 1 0 0 0 0

24 41 1 0 0 0 0

M END): 18 ms

reading 41 atoms

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41 atoms created

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Wikipedia	License
Indometacin, also known as indomethacin, is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does this by inhibiting cyclooxygenase, an enzyme that catalyzes the production of prostaglandins. It was patented in 1961 and approved for medical use in 1963. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 256th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
Read full article at Wikipedia

Formula

C19H16ClNO4

Net Charge

Average Mass

357.78800

Monoisotopic Mass

357.07679

InChI

InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)

InChIKey

CGIGDMFJXJATDK-UHFFFAOYSA-N

SMILES

COc1ccc2n(C(=O)c3ccc(Cl)cc3)c(C)c(CC(O)=O)c2c1

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	drug metabolite xenobiotic metabolite Any metabolite produced by metabolism of a xenobiotic compound. 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. 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. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	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. gout suppressant A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout. 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.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	indometacin (CHEBI:49662) has role analgesic (CHEBI:35480) indometacin (CHEBI:49662) has role drug metabolite (CHEBI:49103) indometacin (CHEBI:49662) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544) indometacin (CHEBI:49662) has role environmental contaminant (CHEBI:78298) indometacin (CHEBI:49662) has role gout suppressant (CHEBI:35845) indometacin (CHEBI:49662) has role non-steroidal anti-inflammatory drug (CHEBI:35475) indometacin (CHEBI:49662) has role xenobiotic (CHEBI:35703) indometacin (CHEBI:49662) has role xenobiotic metabolite (CHEBI:76206) indometacin (CHEBI:49662) is a N-acylindole (CHEBI:75884) indometacin (CHEBI:49662) is a aromatic ether (CHEBI:35618) indometacin (CHEBI:49662) is a indole-3-acetic acids (CHEBI:24803) indometacin (CHEBI:49662) is a monochlorobenzenes (CHEBI:83403)

Incoming	acemetacin (CHEBI:31162) has functional parent indometacin (CHEBI:49662) oxametacin (CHEBI:76255) has functional parent indometacin (CHEBI:49662) proglumetacin (CHEBI:76263) has functional parent indometacin (CHEBI:49662)

IUPAC Name

[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid

INNs	Sources
indometacin	ChemIDplus
indometacina	ChemIDplus
indometacine	ChemIDplus
indometacinum	ChemIDplus

Synonyms	Sources
1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid	ChemIDplus
Indocin	ChemIDplus
Indomethacin	KEGG COMPOUND
{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid	PDBeChem

Brand Names	Sources
Aconip	KEGG DRUG
Indocin	KEGG DRUG

Manual Xrefs	Databases
1440	DrugCentral
BE379378	Patent
C00030512	KNApSAcK
C01926	KEGG COMPOUND
CPD-10545	MetaCyc
D00141	KEGG DRUG
DB00328	DrugBank
HMDB0014473	HMDB
IMN	PDBeChem
Indometacin	Wikipedia
LSM-3275	LINCS
US3161654	Patent
View more database links

Registry Numbers	Types	Sources
1446006	Gmelin Registry Number	Gmelin
497341	Beilstein Registry Number	Beilstein
497341	Reaxys Registry Number	Reaxys
53-86-1	CAS Registry Number	NIST Chemistry WebBook
53-86-1	CAS Registry Number	ChemIDplus

Citations

Last Modified

15 June 2017

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag

CHEBI:49662 - indometacin

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