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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
Structure of INDOMETHACIN SODIUM

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

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

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

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
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

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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Evaluation of the effects of some non-steroid anti-inflammatory agents on the gastric mucosa].
1976 Jul 7
Plaunotol prevents indomethacin-induced gastric mucosal injury in rats by inhibiting neutrophil activation.
1999 Apr
Seizures induced by NSAID.
1999 Jan
Spinal antinociceptive effect of epidural nonsteroidal antiinflammatory drugs on nitric oxide-induced hyperalgesia in rats.
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
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
Capsaicin-sensitive afferent sensory nerves in modulating gastric mucosal defense against noxious agents.
1999 Nov
Effect of anti-CD11b (alphaM-MAC-1) and anti-CD54 (ICAM-1) monoclonal antibodies on indomethacin induced chronic ileitis in rats.
1999 Nov
Tubulointerstitial nephritis with anti-neutrophil cytoplasmic antibody following indomethacin treatment.
1999 Nov
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.
1999 Nov 26
Reactive oxygen species are involved in the apoptosis induced by nonsteroidal anti-inflammatory drugs in cultured gastric cells.
1999 Nov 3
Indomethacin induced gastropathy in CD18, intercellular adhesion molecule 1, or P-selectin deficient mice.
1999 Oct
Dual action of nitric oxide in pathogenesis of indomethacin-induced small intestinal ulceration in rats.
1999 Sep
Sulindac inhibits activation of the NF-kappaB pathway.
1999 Sep 17
[Effect of carrageenan and indomethacin on the growth of a murine fibrosarcoma].
2000
Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons.
2000
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
Characterization of M cell development during indomethacin-induced ileitis in rats.
2000 Feb
Enhanced protein denaturation in indomethacin-treated cells.
2000 Jan
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
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
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
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
A case of living-related kidney transplantation in Bartter's syndrome.
2000 Oct
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.
2001
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
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
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

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 Mon Mar 31 17:56:52 GMT 2025
Edited
by admin
on Mon Mar 31 17:56:52 GMT 2025
Record UNII
0IMX38M2GG
Record Status Validated (UNII)
Record Version
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Name Type Language
INDOMETHACIN SODIUM SALT TRIHYDRATE
MI  
Preferred Name English
INDOMETHACIN SODIUM
ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
INDOMETHACIN SODIUM TRIHYDRATE
Common Name English
INDOMETACIN SODIUM HYDRATE [JAN]
Common Name English
INDOMETHACIN SODIUM [USAN]
Common Name English
SODIUM INDOMETHACIN TRIHYDRATE
Common Name English
INDOMETHACIN SODIUM [ORANGE BOOK]
Common Name English
INDOMETHACIN SODIUM [VANDF]
Common Name English
SODIUM 1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYLINDOLE-3-ACETATE, TRIHYDRATE
Systematic Name English
1H-INDOLE-3-ACETIC ACID, 1-(4-CHLOROBENZOYL)-5-METHOXY-2-METHYL-, SODIUM SALT, TRIHYDRATE
Common Name English
Indometacin sodium [WHO-DD]
Common Name English
Indometacin sodium trihydrate [WHO-DD]
Common Name English
INDOMETACIN SODIUM TRIHYDRATE
Common Name English
INDOMETACIN SODIUM [JAN]
Common Name English
INDOMETACIN SODIUM HYDRATE
Common Name English
INDOMETHACIN SODIUM SALT TRIHYDRATE [MI]
Common Name English
INDOMETACIN SODIUM [MART.]
Common Name English
INDOMETHACIN SODIUM [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
Code System Code Type Description
MERCK INDEX
m6279
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY Merck Index
SMS_ID
100000086425
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
ChEMBL
CHEMBL6
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PRIMARY
RXCUI
258329
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID00225256
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
DRUG BANK
DBSALT001435
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
CAS
74252-25-8
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
WIKIPEDIA
Indomethacin sodium
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
DAILYMED
0IMX38M2GG
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
RXCUI
1294612
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
ALTERNATIVE
USAN
X-78
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PRIMARY
PUBCHEM
23674731
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PRIMARY
FDA UNII
0IMX38M2GG
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
NCI_THESAURUS
C47999
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
EVMPD
SUB02677MIG
Created by admin on Mon Mar 31 17:56:52 GMT 2025 , Edited by admin on Mon Mar 31 17:56:52 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
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
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
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY