I7378

Indomethacin

Name: Indomethacin
Brand: SIGMA

98.5-100.5% (in accordance with EP), powder or crystals, COX inhibitor

Synonym(s):

1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₆ClNO₄

CAS Number:

53-86-1

Molecular Weight:

357.79

NACRES:

NA.77

PubChem Substance ID:

24278173

UNSPSC Code:

12161501

EC Number:

200-186-5

MDL number:

MFCD00057095

Beilstein/REAXYS Number:

497341

Product Name

Indomethacin, 98.5-100.5% (in accordance with EP)

InChI key

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)

SMILES string

COc1ccc2n(c(C)c(CC(O)=O)c2c1)C(=O)c3ccc(Cl)cc3

biological source

synthetic

assay

98.5-100.5% (in accordance with EP)

form

powder or crystals

loss

≤0.5% loss on drying

mp

158-162 °C

mode of action

enzyme | inhibits

Quality Level

200

Gene Information

human ... ALB(213), ALOX5(240), ELA2(1991), GPR44(11251), IL1A(3552), PLA2G1B(5319), PTGDR(5729), PTGS1(5742), PTGS2(5743)
mouse ... Alox5(11689), Ptgdr(19214), Ptger1(19216), Ptger2(19217), Ptger3(19218), Ptger4(19219), Ptgs1(19224)
rat ... Alox5(25290), Ptgs1(24693), Ptgs2(29527)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Indomethacin has been used:

as a medium supplement in osteogenic and adipogenic differentiation assays in human bone marrow stem cells
as a medium supplement in bovine amniotic fluid stem cells (BAFSCs) culture
in the inhibition of prostaglandin E2 (PGE2) in T cells

Biochem/physiol Actions

Cyclooxygenase (COX) inhibitor that is relatively selective for COX-1.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Indomethacin is an inhibitor of the enzyme cyclooxygenase 1 and 2. Indomethacin elicits side effects in gastrointestinal tract, kidney and cerebrum. Indomethacin, along with ibuprofen, is effective for treating patent ductus arteriosus (PDA) in infants with respiratory distress syndrome. Rectal indomethacin is effective in treating endoscopic retrograde cholangiography (ERCP) induced pancreatitis.

pictograms

GHS06

signalword

Danger

hcodes

H300

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 1 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Therapeutic potential of amniotic fluid stem cells to treat bilateral ovarian dystrophy in dairy cows in a subtropical region

Chang LB, et al.

Reproduction in domestic animals = Zuchthygiene, 53(2), 433-441 (2018)

A comparison of ibuprofen and indomethacin for closure of patent ductus arteriosus

Van Overmeire B, et al.

The New England Journal of Medicine, 343(10), 674-681 (2000)

Modulation of miRNAs by Vitamin C in Human Bone Marrow Stromal Cells

Kolhe R, et al.

Nutrients, 10(2), 186-186 (2018)

Suppression of T cells by mesenchymal and cardiac progenitor cells is partly mediated via extracellular vesicles

van den Akker F, et al.

Heliyon, 4(6), e00642-e00642 (2018)

Effectiveness of the use of Rectal Indometacin in the prevention of post-CPRE pancreatitis in the Naval Medical Center.

Islava EE, et al.

INTERNATIONAL JOURNAL OF ADVANCED MULTIDISCIPLINARY RESEARCH, 5(11), 44-51 (2018)

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