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Indomethacin N-octyl amide

Catalog No.
C5591
potent but non-selective inhibitor of both COX-1 and COX-2
Grouped product items
SizePriceStock Qty
5mg
$113.00
Ship with 5-10 days
10mg
$200.00
Ship with 5-10 days
50mg
$878.00
Ship with 5-10 days

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Email: [email protected]

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Background

Indomethacin N-octyl amide is a potent and non-selective inhibitor of both COX-1 and COX-2 [1].

Cyclooxygenase (COX) is the key enzyme required for the conversion of arachidonic acid to prostaglandins. Cyclooxygenase enzymes have been involved in diverse physiological situations and disease processes ranging from inflammation to cancer. Until now, two cyclooxygenase isoforms have been identified, COX-1 and COX-2. The COX-1 enzyme is produced constitutively (i.e., gastric mucosa) and COX-2 is inducible (i.e., sites of inflammation) [2].

Indomethacin is a potent but non-selective inhibitor of both COX-1 and COX-2. Indomethacin is a substituted indole acetic acid, wherein the carboxylate can be derivitized as an ester or amide. Conversion of indomethacin into ester and amide derivatives provides a facile strategy for generating highly selective COX-2 inhibitors. Indomethacin N-octyl amide inhibited the activity of ovine COX-1 and human recombinant COX-2 with the IC50 values of 66 μM and 40 nM, respectively. While the IC50 of indomethacin for the inhibition of COX-1 and COX-2 were 0.67 μM and 0.05 μM, respectively [1].

References:
[1] Kalgutkar A S, Marnett A B, Crews B C, et al.  Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors[J]. Journal of medicinal chemistry, 2000, 43(15): 2860-2870.
[2] Dubois R N, Abramson S B, Crofford L, et al.  Cyclooxygenase in biology and disease[J]. The FASEB journal, 1998, 12(12): 1063-1073.

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt469.0
Cas No.282728-65-8
FormulaC27H33ClN2O3
Solubility≤2mg/ml in ethanol;27mg/ml in dimethyl formamide
Chemical NameN-octyl-1-(4-chlorobenzoyl)-5-methoxy-1H-indole-3-acetamide
SDFDownload SDF
Canonical SMILESClC1=CC=C(C(N2C(C=CC(OC)=C3)=C3C(CC(N([H])CCCCCCCC)=O)=C2C)=O)C=C1
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

Indomethacin N-octyl amide