I7378

Sigma-Aldrich

Indomethacin

98.5-100.5% (in accordance with BP)

Synonym(s):
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid
Empirical Formula (Hill Notation):
C19H16ClNO4
CAS Number:
Molecular Weight:
357.79
Beilstein/REAXYS Number:
497341
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

assay

98.5-100.5% (in accordance with BP)

form

powder or crystals

impurities

≤0.1% sulphated ash
≤0.5% related substance (TLC)
≤20 ppm heavy metals

loss

≤0.5% loss on drying

mp

158-162 °C

Mode of action

enzyme | inhibits

originator

Pfizer

SMILES string

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

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)

InChI key

CGIGDMFJXJATDK-UHFFFAOYSA-N

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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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.

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

Packaging

10, 25, 100 g in glass bottle

Biochem/physiol Actions

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

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGI

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
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)
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)
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