U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H16ClNO4
Molecular Weight 357.788
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOMETHACIN

SMILES

COC1=CC2=C(C=C1)N(C(=O)C3=CC=C(Cl)C=C3)C(C)=C2CC(O)=O

InChI

InChIKey=CGIGDMFJXJATDK-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C19H16ClNO4
Molecular Weight 357.788
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Indometacin (INN and BAN) or indomethacin (AAN, USAN, and former BAN) is a nonsteroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling from inflammation. Indomethacin has analgesic, anti-inflammatory, and antipyretic properties. The mechanism of action of Indometacin, like that of other NSAIDs, is not completely understood but involves inhibition of cyclooxygenase (COX-1 and COX-2). Indomethacin is a potent inhibitor of prostaglandin synthesis in vitro. Indomethacin concentrations reached during therapy have produced in vivo effects. Prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain in animal models. Prostaglandins are mediators of inflammation. Because indomethacin is an inhibitor of prostaglandin synthesis, its mode of action may be due to a decrease of prostaglandins in peripheral tissues. Indometacin is indicated for: Moderate to severe rheumatoid arthritis including acute flares of chronic disease, Moderate to severe ankylosing spondylitis, Moderate to severe osteoarthritis, Acute painful shoulder (bursitis and/or tendinitis), Acute gouty arthritis. In general, adverse effects seen with indomethacin are similar to all other NSAIDs. For instance, indometacin inhibits both cyclooxygenase-1 and cyclooxygenase-2, it inhibits the production of prostaglandins in the stomach and intestines, which maintain the mucous lining of the gastrointestinal tract. Indometacin, therefore, like other non-selective COX inhibitors can cause peptic ulcers. These ulcers can result in serious bleeding and/or perforation requiring hospitalization of the patient. To reduce the possibility of peptic ulcers, indomethacin should be prescribed at the lowest dosage needed to achieve a therapeutic effect, usually between 50–200 mg/day. It should always be taken with food. Nearly all patients benefit from an ulcer protective drug (e.g. highly dosed antacids, ranitidine 150 mg at bedtime, or omeprazole 20 mg at bedtime). Other common gastrointestinal complaints, including dyspepsia, heartburn and mild diarrhea are less serious and rarely require discontinuation of indomethacin.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Letter: Aspirin sensitivity: other drugs.
1975 Feb
[Clinical results of a multicentral double-blind examination of naproxen compared to indomethacin in chronic rheumatoid arthritis, ankylosing spondylitis, and osteoarthrosis].
1975 Feb
[Evaluation of the effects of some non-steroid anti-inflammatory agents on the gastric mucosa].
1976 Jul 7
[Intrahepatic cholestasis following treatment with penicillamine D and indomethacine].
1976 May 28
Premature onset of labor, neonatal patent ductus arteriosus, and prostaglandin synthetase antagonists--a rat model of a human problem.
1979 Sep 15
Persistent pulmonary hypertension after maternal naproxen ingestion in a term newborn: a case report.
2000
[Effect of carrageenan and indomethacin on the growth of a murine fibrosarcoma].
2000
Matrix metalloproteinases 2 and 9 in indomethacin-induced rat gastric ulcer.
2000
Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons.
2000
The role of nitric oxide and prostaglandin E2 on the hyperalgesia induced by excitatory amino acids in rats.
2000 Apr
Indomethacin inhibits endothelial cell proliferation by suppressing cell cycle proteins and PRB phosphorylation: a key to its antiangiogenic action?
2000 Aug
Non-steroidal anti-inflammatory drugs with different cyclooxygenase inhibitory profiles that prevent aberrant crypt foci formation but vary in acute gastrotoxicity in a rat model.
2000 Dec
Salicylate-induced growth arrest is associated with inhibition of p70s6k and down-regulation of c-myc, cyclin D1, cyclin A, and proliferating cell nuclear antigen.
2000 Dec 8
Neuropeptide Y enhances potassium excretion by mechanisms distinct from those controlling sodium excretion.
2000 Feb
Bartter syndrome in a neonate: early treatment with indomethacin.
2000 Feb
Induction of antitumor immunity by indomethacin.
2000 Feb
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Enhanced protein denaturation in indomethacin-treated cells.
2000 Jan
Inhibition of carrageenan-induced edema by indomethacin or sodium salicylate does not prevent the increase of nerve growth factor in the rat hind paw.
2000 Jan 14
Transcriptional induction of Nur77 by indomethacin that results in apoptosis of colon cancer cells.
2000 Jul
Ibuprofen as effective as indomethacin for patent ductus arteriosus.
2000 Jul 25
Indomethacin-induced apoptosis in esophageal adenocarcinoma cells involves upregulation of Bax and translocation of mitochondrial cytochrome C independent of COX-2 expression.
2000 Jul-Aug
The influence of indomethacin on the acth secretion induced by central stimulation of adrenergic receptors.
2000 Jun
Regrowth of 5-fluorouracil-treated human colon cancer cells is prevented by the combination of interferon gamma, indomethacin, and phenylbutyrate.
2000 Jun 15
Effect of indomethacin on IL-1beta, IL-6 and TNFalpha production by mononuclear cells of preterm newborns and adults.
2000 Mar
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
2000 Mar
Overexpression of protein kinase C-beta1 isoenzyme suppresses indomethacin-induced apoptosis in gastric epithelial cells.
2000 Mar
Effects of hydrogen peroxide scavenger Catalase on villous microcirculation in the rat small intestine in a model of inflammatory bowel disease.
2000 May
Indomethacin induces apoptosis and inhibits proliferation in chronic myeloid leukemia cells.
2000 May
Role of endothelin-converting enzyme-1 in the suppression of constitutive nitric oxide synthase in rat gastric mucosal injury by indomethacin.
2000 Nov
Effect of indomethacin on blood pressure in elderly people with essential hypertension well controlled on amlodipine or enalapril.
2000 Nov
Inhibition of proteolysis by a cyclooxygenase inhibitor, indomethacin.
2000 Nov
Keratinocyte growth factor-2 (FGF-10) promotes healing of experimental small intestinal ulceration in rats.
2000 Nov
Inhibition of inducible nitric oxide synthase gene expression by indomethacin or ibuprofen in beta-amyloid protein-stimulated J774 cells.
2000 Nov 17
Role of BAX in the apoptotic response to anticancer agents.
2000 Nov 3
Indomethacin inhibits the accumulation of tumor cells in mouse lungs and subsequent growth of lung metastases.
2000 Nov-Dec
Protection by polaprezinc, an anti-ulcer drug, against indomethacin-induced apoptosis in rat gastric mucosal cells.
2000 Sep
Suppressed injury-induced rise in spinal prostaglandin E2 production and reduced early thermal hyperalgesia in iNOS-deficient mice.
2000 Sep 1
A comparison of ibuprofen and indomethacin for closure of patent ductus arteriosus.
2000 Sep 7
Two opposing effects of non-steroidal anti-inflammatory drugs on the expression of the inducible cyclooxygenase. Mediation through different signaling pathways.
2000 Sep 8
Does exposure to magnesium sulfate in utero decrease the risk of necrotizing enterocolitis in premature infants?
2001 Feb
Upregulation of angiotensin-converting enzyme by vascular endothelial growth factor.
2001 Feb
Lack of small intestinal ulcerogenecity of nitric oxide-releasing indomethacin, NCX-530, in rats.
2001 Feb
Increased 15-HPETE production decreases prostacyclin synthase activity during oxidant stress in aortic endothelial cells.
2001 Feb 1
An investigation into the thermal behaviour of an amorphous drug using low frequency dielectric spectroscopy and modulated temperature differential scanning calorimetry.
2001 Jan
Effect of Lactobacillus ingestion on the gastrointestinal mucosal barrier alterations induced by indometacin in humans.
2001 Jan
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans.
2001 Jan
Effect of indomethacin on gallbladder inflammation and contractility during acute cholecystitis.
2001 Mar
Methotrexate and early postoperative complications in patients with rheumatoid arthritis undergoing elective orthopaedic surgery.
2001 Mar
Indomethacin prevents the induction of inducible nitric oxide synthase in murine peritoneal macrophages and decreases their nitric oxide production.
2001 Mar 9
Patents

Sample Use Guides

In Vivo Use Guide
INDOCIN 75-150 mg daily in 3 or 4 divided doses.
Route of Administration: Oral
In Vitro Use Guide
U251 cells were incubated for 24 h with different concentrations of indomethacin (0.03, 0.06, 0.13, 0.25, 0.5, 1 mkM), diclofenac (DIC),naproxen (NAP), or ketoprofen (KET), and the cell viability was assessed by MTT or crystal violet (CV) tests.
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:32:15 UTC 2019
Edited
by admin
on Mon Oct 21 22:32:15 UTC 2019
Record UNII
XXE1CET956
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDOMETHACIN
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
ACONIP
Brand Name English
INDO-LEMMON
Brand Name English
1H-INDOLE-3-ACETIC ACID, 1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-
Common Name English
INDOMETACINUM [WHO-IP LATIN]
Common Name English
INDOMETACIN [MART.]
Common Name English
NSC-77541
Code English
INDOMETACIN
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
INDOMETACIN [INN]
Common Name English
INDOMETACIN [EP]
Common Name English
INDOMETHACIN [MI]
Common Name English
(1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOL-3-YL)ACETIC ACID
Systematic Name English
INDOMETHACIN [ORANGE BOOK]
Common Name English
ACEMETACIN IMPURITY B [EP]
Common Name English
INDOMETACIN [WHO-DD]
Common Name English
INDOMETHACIN [USP]
Common Name English
REUMACIDE
Common Name English
TIVORBEX
Brand Name English
INDOMETHACIN [USP-RS]
Common Name English
INDOMETHACIN [VANDF]
Common Name English
1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID
Common Name English
INDOMETHACIN [USAN]
Common Name English
DURAMETACIN
Common Name English
INDOMETHACIN [HSDB]
Common Name English
INDOCIN
Brand Name English
INDOMETACIN [WHO-IP]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000160
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
NCI_THESAURUS C1323
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-VATC QS01BC01
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-VATC QC01EB03
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
NCI_THESAURUS C54677
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
NDF-RT N0000175721
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
LIVERTOX 505
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-ATC M02AA23
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
NDF-RT N0000175722
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-VATC QM01AB01
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-ATC M01AB01
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-ATC S01BC01
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-VATC QM02AA23
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-ATC S01CC02
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-VATC QM01AB51
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-ATC M01AB51
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
WHO-ATC C01EB03
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
Code System Code Type Description
LactMed
53-86-1
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
ChEMBL
CHEMBL6
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
DRUG BANK
DB00328
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
MERCK INDEX
M6279
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY Merck Index
RXCUI
5781
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY RxNorm
MESH
D007213
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
EPA CompTox
53-86-1
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
EVMPD
SUB08180MIG
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
INN
1524
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
HSDB
53-86-1
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
PUBCHEM
3715
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
INDOMETHACIN
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY Description: A white or a pale yellow, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; sparingly soluble in ethanol (~750 g/l) TS and ether R. Category: Analgesic; anti-inflammatory. Storage: Indometacin should be kept in a well-closed container, protected from light. Additional information: Indometacin exhibits polymorphism. The polymorph specified in the monograph corresponds to the crystal form of indometacin RS.Definition: Indometacin contains not less than 98.0% and not more than 101.0% of C19H16ClNO4, calculated with reference to the dried substance.
NCI_THESAURUS
C576
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
CAS
53-86-1
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
IUPHAR
1909
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-186-5
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
WIKIPEDIA
INDOMETACIN
Created by admin on Mon Oct 21 22:32:15 UTC 2019 , Edited by admin on Mon Oct 21 22:32:15 UTC 2019
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
DEGRADENT -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY