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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=CC=C2N(C(=O)C3=CC=C(Cl)C=C3)C(C)=C(CC(O)=O)C2=C1

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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INDOCIN

Approved Use

TIVORBEX 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 Date

1965
Primary
INDOCIN

Approved Use

TIVORBEX 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 Date

1965
Primary
INDOCIN

Approved Use

TIVORBEX 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 Date

1965
Primary
INDOCIN

Approved Use

TIVORBEX 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 Date

1965
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
Doses

Doses

DosePopulationAdverse events​
0.9 g single, oral
Overdose
Dose: 0.9 g
Route: oral
Route: single
Dose: 0.9 g
Sources: Page: p.152
unhealthy, 15
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.152
Disc. AE: Vomiting, Nausea...
AEs leading to
discontinuation/dose reduction:
Vomiting
Nausea (mild)
Anorexia (mild)
Sources: Page: p.152
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Other AEs: Headache, Pruritus...
Other AEs:
Headache (below serious, 11 patient)
Pruritus (below serious, 5 patients)
Sources:
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 92
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 92
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (below serious, 34 patients)
Vomiting (below serious, 11 patient)
Constipation (below serious, 8 patients)
Sources:
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Other AEs: Deep vein thrombosis, Headache...
Other AEs:
Deep vein thrombosis (serious, 1 patient)
Headache (below serious, 13 patients)
Pruritus (below serious, 1 patient)
Presyncope (below serious, 5 patients)
Sources:
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (below serious, 36 patients)
Vomiting (below serious, 12 patients)
Constipation (below serious, 7 patients)
Post procedural haemorrhage (below serious, 7 patients)
Sources:
40 mg 3 times / day multiple, oral
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Other AEs: Headache, Pruritus...
Other AEs:
Headache (below serious, 12 patients)
Pruritus (below serious, 3 patients)
Sources:
40 mg 3 times / day multiple, oral
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
unhealthy, adult
n = 94
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 94
Sources:
Other AEs: Headache, Vomiting...
Other AEs:
Headache (below serious, 17 patients)
Vomiting (below serious, 9 patients)
Sources:
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Disc. AE: Cardiac thrombosis, Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Cardiac thrombosis (serious)
Myocardial infarction (grade 3-5)
Stroke (grade 3-5)
Gastrointestinal disorder NOS (serious)
Bleeding (grade 3-5)
Ulceration (grade 3-5)
Perforation stomach (grade 3-5)
Perforation of intestine (grade 3-5)
Sources:
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Other AEs: Gingival bleeding, Application site pruritus...
Other AEs:
Gingival bleeding (below serious, 1 patient)
Application site pruritus (below serious, 1 patient)
Inflammation (below serious, 1 patient)
Nasopharyngitis (below serious, 1 patient)
Ligament sprain (below serious, 1 patient)
Rash (below serious, 2 patients)
Drug eruption (below serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Vomiting Disc. AE
0.9 g single, oral
Overdose
Dose: 0.9 g
Route: oral
Route: single
Dose: 0.9 g
Sources: Page: p.152
unhealthy, 15
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.152
Anorexia mild
Disc. AE
0.9 g single, oral
Overdose
Dose: 0.9 g
Route: oral
Route: single
Dose: 0.9 g
Sources: Page: p.152
unhealthy, 15
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.152
Nausea mild
Disc. AE
0.9 g single, oral
Overdose
Dose: 0.9 g
Route: oral
Route: single
Dose: 0.9 g
Sources: Page: p.152
unhealthy, 15
n = 1
Health Status: unhealthy
Condition: Knee pain
Age Group: 15
Sex: F
Population Size: 1
Sources: Page: p.152
Headache below serious, 11 patient
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Pruritus below serious, 5 patients
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Vomiting below serious, 11 patient
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 92
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 92
Sources:
Nausea below serious, 34 patients
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 92
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 92
Sources:
Constipation below serious, 8 patients
20 mg 3 times / day multiple, oral
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
unhealthy, adult
n = 92
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 92
Sources:
Pruritus below serious, 1 patient
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Headache below serious, 13 patients
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Presyncope below serious, 5 patients
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Deep vein thrombosis serious, 1 patient
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 91
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 91
Sources:
Vomiting below serious, 12 patients
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Nausea below serious, 36 patients
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Constipation below serious, 7 patients
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Post procedural haemorrhage below serious, 7 patients
40 mg 2 times / day multiple, oral
Dose: 40 mg, 2 times / day
Route: oral
Route: multiple
Dose: 40 mg, 2 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Headache below serious, 12 patients
40 mg 3 times / day multiple, oral
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Pruritus below serious, 3 patients
40 mg 3 times / day multiple, oral
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
unhealthy, adult
n = 93
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 93
Sources:
Headache below serious, 17 patients
40 mg 3 times / day multiple, oral
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
unhealthy, adult
n = 94
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 94
Sources:
Vomiting below serious, 9 patients
40 mg 3 times / day multiple, oral
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
unhealthy, adult
n = 94
Health Status: unhealthy
Condition: Acute Postoperative Pain
Age Group: adult
Sex: M+F
Population Size: 94
Sources:
Bleeding grade 3-5
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Myocardial infarction grade 3-5
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Perforation of intestine grade 3-5
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Perforation stomach grade 3-5
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Stroke grade 3-5
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Ulceration grade 3-5
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Cardiac thrombosis serious
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Gastrointestinal disorder NOS serious
Disc. AE
50 mg 3 times / day multiple, oral
Recommended
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Bursitis|Tendinitis|Gouty arthritis
Sources:
Application site pruritus below serious, 1 patient
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Drug eruption below serious, 1 patient
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Gingival bleeding below serious, 1 patient
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Inflammation below serious, 1 patient
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Ligament sprain below serious, 1 patient
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Nasopharyngitis below serious, 1 patient
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Rash below serious, 2 patients
0.35 % 2 times / day multiple, topical
Dose: 0.35 %, 2 times / day
Route: topical
Route: multiple
Dose: 0.35 %, 2 times / day
Sources:
unhealthy
n = 135
Health Status: unhealthy
Condition: sprained ankle
Population Size: 135
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
Decrease in nucleophosmin/B23 mRNA and telomerase activity during indomethacin-induced apoptosis of gastric KATO-III cancer cells.
1999 Dec
Spinal antinociceptive effect of epidural nonsteroidal antiinflammatory drugs on nitric oxide-induced hyperalgesia in rats.
1999 Jul
The influence of indomethacin on the metabolism and cytokine secretion of human aneurysmal aorta.
1999 Jul
Prostaglandins and leukotriene B4 are potent inhibitors of 11beta-hydroxysteroid dehydrogenase type 2 activity in human choriocarcinoma JEG-3 cells.
1999 Jul
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
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
The effect of indomethacin on the cytokine cascade and body temperature following burn injury in rats.
1999 Jun
Induction of stromelysin gene expression by tumor necrosis factor alpha is inhibited by dexamethasone, salicylate, and N-acetylcysteine in synovial fibroblasts.
1999 Jun
Role of endothelin-1 and constitutive nitric oxide synthase in gastric mucosal resistance to indomethacin injury: effect of antiulcer agents.
1999 May
Indomethacin treatment slows disease progression and enhances a Th1 response in susceptible BALB/c mice infected with Leishmania major.
1999 May
Indomethacin inhibits expansion of experimental aortic aneurysms via inhibition of the cox2 isoform of cyclooxygenase.
1999 May
Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells.
1999 May 21
Indomethacin reduces the skin thermal damage in hyperthermic treatment of experimental malignant tumors.
1999 May-Jun
Effect of anti-CD11b (alphaM-MAC-1) and anti-CD54 (ICAM-1) monoclonal antibodies on indomethacin induced chronic ileitis in rats.
1999 Nov
Indomethacin treatment decreases renal blood flow velocity in human neonates.
1999 Nov
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.
1999 Nov 26
Indomethacin induced gastropathy in CD18, intercellular adhesion molecule 1, or P-selectin deficient mice.
1999 Oct
PPARdelta is an APC-regulated target of nonsteroidal anti-inflammatory drugs.
1999 Oct 29
Indomethacin-induced postoperative psychosis.
1999 Sep
Sulindac inhibits activation of the NF-kappaB pathway.
1999 Sep 17
Persistent pulmonary hypertension after maternal naproxen ingestion in a term newborn: a case report.
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
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
Induction of antitumor immunity by indomethacin.
2000 Feb
Characterization of M cell development during indomethacin-induced ileitis in rats.
2000 Feb
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Randomized double-blind controlled trial comparing the effects of ibuprofen with indomethacin on cerebral hemodynamics in preterm infants with patent ductus arteriosus.
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
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
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
In vivo indomethacin treatment causes microglial activation in adult mice.
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
Effect of indomethacin on blood pressure in elderly people with essential hypertension well controlled on amlodipine or enalapril.
2000 Nov
A comparison of ibuprofen and indomethacin for closure of patent ductus arteriosus.
2000 Sep 7
Effect of the nonsteroidal anti-inflammatory drug indomethacin on proliferation and apoptosis of colon carcinoma cells.
2001
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
An investigation into the thermal behaviour of an amorphous drug using low frequency dielectric spectroscopy and modulated temperature differential scanning calorimetry.
2001 Jan
Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans.
2001 Jan
Agonist-specific regulation of monocyte chemoattractant protein-1 expression by cyclooxygenase metabolites in hepatic stellate cells.
2001 Mar
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
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.
2001 Mar 9
Patents

Sample Use Guides

INDOCIN 75-150 mg daily in 3 or 4 divided doses.
Route of Administration: Oral
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 Fri Dec 15 15:07:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:35 GMT 2023
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-
Systematic Name English
INDOMETACINUM [WHO-IP LATIN]
Common Name English
1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOLE-3-ACETIC ACID
Systematic 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
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
INDOMETHACIN [USP MONOGRAPH]
Common Name English
ACEMETACIN IMPURITY B [EP IMPURITY]
Common Name English
REUMACIDE
Common Name English
TIVORBEX
Brand Name English
INDOMETHACIN [USP-RS]
Common Name English
INDOMETHACIN [VANDF]
Common Name English
NSC-757061
Code English
Indometacin [WHO-DD]
Common Name English
1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID
Common Name English
INDOMETACIN [JAN]
Common Name English
INDOMETHACIN [USAN]
Common Name English
DURAMETACIN
Common Name English
INDOMETHACIN [HSDB]
Common Name English
INDOCIN
Brand Name English
INDOMETACIN [EP MONOGRAPH]
Common Name English
INDOMETACIN [WHO-IP]
Common Name English
Classification Tree Code System Code
NDF-RT N0000000160
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-VATC QS01BC01
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-VATC QC01EB03
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
NCI_THESAURUS C54677
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
LIVERTOX NBK548001
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-ATC M02AA23
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
NDF-RT N0000175722
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-VATC QM01AB01
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-ATC M01AB01
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-ATC S01BC01
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-VATC QM02AA23
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-ATC S01CC02
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-VATC QM01AB51
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-ATC M01AB51
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
WHO-ATC C01EB03
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL6
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
DRUG BANK
DB00328
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
MERCK INDEX
m6279
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY Merck Index
RXCUI
5781
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY RxNorm
MESH
D007213
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
LACTMED
Indomethacin
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
DAILYMED
XXE1CET956
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020740
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
EVMPD
SUB08180MIG
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
SMS_ID
100000092758
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
CHEBI
49662
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
NSC
757061
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
FDA UNII
XXE1CET956
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
INN
1524
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
NSC
77541
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
RS_ITEM_NUM
1341001
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
HSDB
3101
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
PUBCHEM
3715
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
INDOMETHACIN
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
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.
DRUG CENTRAL
1440
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
NCI_THESAURUS
C576
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
CAS
53-86-1
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
IUPHAR
1909
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-186-5
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
WIKIPEDIA
INDOMETACIN
Created by admin on Fri Dec 15 15:07:35 GMT 2023 , Edited by admin on Fri Dec 15 15:07:35 GMT 2023
PRIMARY
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TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
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