Merck
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I7378

Sigma-Aldrich

Indomethacin

98.5-100.5% (in accordance with EP)

All Photos(5)
Synonym(s):
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid
Empirical Formula (Hill Notation):
C19H16ClNO4
CAS Number:
53-86-1
Molecular Weight:
357.79
Beilstein:
497341
EC Number:
200-186-5
MDL number:
MFCD00057095
PubChem Substance ID:
24278173
NACRES:
NA.77

biological source

synthetic

Quality Level

200

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

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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This Item
I02000001341001405268
Indomethacin 98.5-100.5% (in accordance with EP)

Sigma-Aldrich

I7378

Indomethacin

Indomethacin European Pharmacopoeia (EP) Reference Standard

I0200000

Indomethacin

Indomethacin United States Pharmacopeia (USP) Reference Standard

USP

1341001

Indomethacin

Indomethacin A non-steroidal anti-inflammatory, cell permeable, antipyretic agent.

Sigma-Aldrich

405268

Indomethacin

form

powder or crystals

form

-

form

-

form

powder

originator

Pfizer

originator

-

originator

-

originator

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

100

biological source

synthetic

biological source

-

biological source

-

biological source

-

loss

≤0.5% loss on drying

loss

-

loss

-

loss

-

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

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.
This compound was developed by Pfizer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
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)
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)
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