I7378

Indomethacin

98.5-100.5% (in accordance with EP)

• 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/REAXYS Number: 497341
• EC Number: 200-186-5
• MDL number: MFCD00057095
• UNSPSC Code: 12161501
• PubChem Substance ID: 24278173
• NACRES: NA.77

Properties

• 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
• 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)

Description

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.

Safety Information

• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges