Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H15ClNO4.Na.3H2O |
Molecular Weight | 433.815 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[Na+].COC1=CC2=C(C=C1)N(C(=O)C3=CC=C(Cl)C=C3)C(C)=C2CC([O-])=O
InChI
InChIKey=UHYAQBLOGVNWNT-UHFFFAOYSA-M
InChI=1S/C19H16ClNO4.Na.3H2O/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);;3*1H2/q;+1;;;/p-1
Molecular Formula | C19H16ClNO4 |
Molecular Weight | 357.788 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.98976928 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02183168 | https://clinicaltrials.gov/ct2/show/NCT02770950 | https://www.ncbi.nlm.nih.gov/pubmed/20503989 | https://www.ncbi.nlm.nih.gov/pubmed/14056924 | https://www.ncbi.nlm.nih.gov/pubmed/27988363
Curator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02183168 | https://clinicaltrials.gov/ct2/show/NCT02770950 | https://www.ncbi.nlm.nih.gov/pubmed/20503989 | https://www.ncbi.nlm.nih.gov/pubmed/14056924 | https://www.ncbi.nlm.nih.gov/pubmed/27988363
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11906281 |
3.0 nM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20503989 |
10.0 nM [IC50] | ||
Target ID: CHEMBL4681 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23432095 |
100.0 nM [IC50] | ||
Target ID: CHEMBL1835 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2547071 |
100.0 nM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12142058 |
|||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12142058 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | INDOCIN Approved UseTIVORBEX is indicated for treatment of mild to moderate acute pain in adults. TIVORBEX is a NSAID indicated for treatment of mild to moderate acute pain in adults (1). Launch Date1965 |
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Primary | INDOCIN Approved UseTIVORBEX is indicated for treatment of mild to moderate acute pain in adults. TIVORBEX is a NSAID indicated for treatment of mild to moderate acute pain in adults (1). Launch Date1965 |
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Primary | INDOCIN Approved UseTIVORBEX is indicated for treatment of mild to moderate acute pain in adults. TIVORBEX is a NSAID indicated for treatment of mild to moderate acute pain in adults (1). Launch Date1965 |
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Primary | INDOCIN Approved UseTIVORBEX is indicated for treatment of mild to moderate acute pain in adults. TIVORBEX is a NSAID indicated for treatment of mild to moderate acute pain in adults (1). Launch Date1965 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 μg/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2369 ng/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7762 ng × h/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.22 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
INDOMETHACIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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[Evaluation of the effects of some non-steroid anti-inflammatory agents on the gastric mucosa]. | 1976 Jul 7 |
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Plaunotol prevents indomethacin-induced gastric mucosal injury in rats by inhibiting neutrophil activation. | 1999 Apr |
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Seizures induced by NSAID. | 1999 Jan |
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Spinal antinociceptive effect of epidural nonsteroidal antiinflammatory drugs on nitric oxide-induced hyperalgesia in rats. | 1999 Jul |
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Differential apoptosis by indomethacin in gastric epithelial cells through the constitutive expression of wild-type p53 and/or up-regulation of c-myc. | 1999 Jul 1 |
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Inhibition of prostaglandin E2 synthesis in abdominal aortic aneurysms: implications for smooth muscle cell viability, inflammatory processes, and the expansion of abdominal aortic aneurysms. | 1999 Jul 6 |
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The effect of indomethacin on the cytokine cascade and body temperature following burn injury in rats. | 1999 Jun |
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Induction of stromelysin gene expression by tumor necrosis factor alpha is inhibited by dexamethasone, salicylate, and N-acetylcysteine in synovial fibroblasts. | 1999 Jun |
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Role of endothelin-1 and constitutive nitric oxide synthase in gastric mucosal resistance to indomethacin injury: effect of antiulcer agents. | 1999 May |
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Indomethacin treatment slows disease progression and enhances a Th1 response in susceptible BALB/c mice infected with Leishmania major. | 1999 May |
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Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells. | 1999 May 21 |
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Indomethacin reduces the skin thermal damage in hyperthermic treatment of experimental malignant tumors. | 1999 May-Jun |
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Capsaicin-sensitive afferent sensory nerves in modulating gastric mucosal defense against noxious agents. | 1999 Nov |
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Effect of anti-CD11b (alphaM-MAC-1) and anti-CD54 (ICAM-1) monoclonal antibodies on indomethacin induced chronic ileitis in rats. | 1999 Nov |
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Tubulointerstitial nephritis with anti-neutrophil cytoplasmic antibody following indomethacin treatment. | 1999 Nov |
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Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions. | 1999 Nov 26 |
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Reactive oxygen species are involved in the apoptosis induced by nonsteroidal anti-inflammatory drugs in cultured gastric cells. | 1999 Nov 3 |
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Indomethacin induced gastropathy in CD18, intercellular adhesion molecule 1, or P-selectin deficient mice. | 1999 Oct |
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Dual action of nitric oxide in pathogenesis of indomethacin-induced small intestinal ulceration in rats. | 1999 Sep |
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Sulindac inhibits activation of the NF-kappaB pathway. | 1999 Sep 17 |
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[Effect of carrageenan and indomethacin on the growth of a murine fibrosarcoma]. | 2000 |
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Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons. | 2000 |
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Neuropeptide Y enhances potassium excretion by mechanisms distinct from those controlling sodium excretion. | 2000 Feb |
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Bartter syndrome in a neonate: early treatment with indomethacin. | 2000 Feb |
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Induction of antitumor immunity by indomethacin. | 2000 Feb |
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Characterization of M cell development during indomethacin-induced ileitis in rats. | 2000 Feb |
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Enhanced protein denaturation in indomethacin-treated cells. | 2000 Jan |
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Randomized double-blind controlled trial comparing the effects of ibuprofen with indomethacin on cerebral hemodynamics in preterm infants with patent ductus arteriosus. | 2000 Jan |
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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 |
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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 |
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Effect of indomethacin on IL-1beta, IL-6 and TNFalpha production by mononuclear cells of preterm newborns and adults. | 2000 Mar |
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In vivo indomethacin treatment causes microglial activation in adult mice. | 2000 Mar |
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Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine. | 2000 Mar |
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Overexpression of protein kinase C-beta1 isoenzyme suppresses indomethacin-induced apoptosis in gastric epithelial cells. | 2000 Mar |
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Indomethacin induces apoptosis and inhibits proliferation in chronic myeloid leukemia cells. | 2000 May |
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Role of endothelin-converting enzyme-1 in the suppression of constitutive nitric oxide synthase in rat gastric mucosal injury by indomethacin. | 2000 Nov |
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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 |
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Keratinocyte growth factor-2 (FGF-10) promotes healing of experimental small intestinal ulceration in rats. | 2000 Nov |
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Inhibition of inducible nitric oxide synthase gene expression by indomethacin or ibuprofen in beta-amyloid protein-stimulated J774 cells. | 2000 Nov 17 |
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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 |
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A case of living-related kidney transplantation in Bartter's syndrome. | 2000 Oct |
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Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
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Indomethacin increases 15-PGDH mRNA expression in HL60 cells differentiated by PMA. | 2001 Feb |
|
Lack of small intestinal ulcerogenecity of nitric oxide-releasing indomethacin, NCX-530, in rats. | 2001 Feb |
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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 |
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Protective role of cyclooxygenase inhibitors in the adverse action of passive cigarette smoking on the initiation of experimental colitis in rats. | 2001 Jan 5 |
|
Agonist-specific regulation of monocyte chemoattractant protein-1 expression by cyclooxygenase metabolites in hepatic stellate cells. | 2001 Mar |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27988363
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
Edited
Mon Mar 31 17:56:52 GMT 2025
by
admin
on
Mon Mar 31 17:56:52 GMT 2025
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Record UNII |
0IMX38M2GG
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1323
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m6279
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100000086425
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CHEMBL6
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258329
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DTXSID00225256
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DBSALT001435
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74252-25-8
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Indomethacin sodium
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0IMX38M2GG
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1294612
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X-78
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23674731
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0IMX38M2GG
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C47999
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SUB02677MIG
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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
The sum of the percentages of indomethacin related compound A and indomethacin related compound B is NMT 0.2%.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
The sum of the percentages of indomethacin related compound A and indomethacin related compound B is NMT 0.2%.
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
USP
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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