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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=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

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
Letter: Aspirin sensitivity: other drugs.
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
Decrease in nucleophosmin/B23 mRNA and telomerase activity during indomethacin-induced apoptosis of gastric KATO-III cancer cells.
1999 Dec
Prostaglandin-independent anovulatory mechanism of indomethacin action: inhibition of tumor necrosis factor alpha-induced sheep ovarian cell apoptosis.
1999 Dec
The effect of indomethacin on the cytokine cascade and body temperature following burn injury in rats.
1999 Jun
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
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
Indomethacin-induced postoperative psychosis.
1999 Sep
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
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
Neuropeptide Y enhances potassium excretion by mechanisms distinct from those controlling sodium excretion.
2000 Feb
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
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
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
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
A case of living-related kidney transplantation in Bartter's syndrome.
2000 Oct
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
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
Stimulation of cyclooxygenase-2-activity by nitric oxide-derived species in rat chondrocyte: lack of contribution to loss of cartilage anabolism.
2001 Apr 15
Indomethacin increases 15-PGDH mRNA expression in HL60 cells differentiated by PMA.
2001 Feb
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
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
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
Comparative effects of indomethacin on cell proliferation and cell cycle progression in tumor cells grown in vitro and in vivo.
2001 Mar 1
Inactivation of creatine kinase during the interaction of indomethacin with horseradish peroxidase and hydrogen peroxide: involvement of indomethacin radicals.
2001 Mar 14
Indomethacin prevents the induction of inducible nitric oxide synthase in murine peritoneal macrophages and decreases their nitric oxide production.
2001 Mar 9
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.
Name Type Language
INDOMETHACIN
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
INDOMETACIN
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Preferred 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 [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 Mon Mar 31 17:47:22 GMT 2025 , Edited by admin on Mon Mar 31 17:47:22 GMT 2025
NCI_THESAURUS C1323
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WHO-VATC QS01BC01
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WHO-VATC QC01EB03
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NCI_THESAURUS C54677
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NDF-RT N0000175721
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LIVERTOX NBK548001
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WHO-ATC M02AA23
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NDF-RT N0000175722
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WHO-VATC QM01AB01
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WHO-ATC M01AB01
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WHO-ATC S01BC01
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WHO-VATC QM02AA23
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WHO-ATC S01CC02
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WHO-VATC QM01AB51
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WHO-ATC M01AB51
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WHO-ATC C01EB03
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Code System Code Type Description
ChEMBL
CHEMBL6
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PRIMARY
DRUG BANK
DB00328
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PRIMARY
MERCK INDEX
m6279
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PRIMARY Merck Index
RXCUI
5781
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PRIMARY RxNorm
MESH
D007213
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PRIMARY
LACTMED
Indomethacin
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PRIMARY
DAILYMED
XXE1CET956
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PRIMARY
EPA CompTox
DTXSID9020740
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PRIMARY
EVMPD
SUB08180MIG
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PRIMARY
SMS_ID
100000092758
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PRIMARY
CHEBI
49662
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PRIMARY
NSC
757061
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PRIMARY
FDA UNII
XXE1CET956
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PRIMARY
INN
1524
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PRIMARY
NSC
77541
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PRIMARY
RS_ITEM_NUM
1341001
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PRIMARY
HSDB
3101
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PRIMARY
PUBCHEM
3715
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
INDOMETHACIN
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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
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PRIMARY
NCI_THESAURUS
C576
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PRIMARY
CAS
53-86-1
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PRIMARY
IUPHAR
1909
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PRIMARY
ECHA (EC/EINECS)
200-186-5
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PRIMARY
WIKIPEDIA
INDOMETACIN
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PRIMARY