Indomethacin N-octyl amide

Cayman Chemical Item Number 70273

Indomethacin N-octyl amide

Description

Indomethacin is a potent but non-selective inhibitor of both COX-1 and COX-2 in sheep and humans.¹ Structurally, indomethacin is a substituted indole acetic acid, wherein the carboxylate can be derivitized as an ester or amide. These derivatives show enhanced selectivity for the COX-2 isoform. For example, the IC₅₀ values of indomethacin N-octyl amide for the inhibition of ovine COX-1 and human recombinant COX-2 are 66 µM and 40 nM, respectively, making it 1,650 times more potent as an inhibitor of COX-2 than COX-1.² While indomethacin itself has an IC₅₀ of 0.05 µM for the inhibition of COX-2, it also inhibits COX-1 with a corresponding IC₅₀ of 0.67 µM.

1 Barnett, J., Chow, J., Ives, D., et al. Purification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and 2 expressed in the baculovirus system. Biochim Biophys Acta 1209 130-139 (1994).

2 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 Med Chem 43 2860-2870 (2000).

Formal Name

N-octyl-1-(4-chlorobenzoyl)-5-methoxy-1H-indole-3-acetamide

Molecular Formula

C₂₇H₃₃ClN₂O₃

Formula Weight

469.0

Formulation

A crystalline solid

Purity

≥98%

λ_max

230, 260, 319 nm

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

ClC1=CC=C(C(N2C(C=CC(OC)=C3)=C3C(CC(N([H])CCCCCCCC)=O)=C2C)=O)C=C1

Background Reading

Barnett, J., Chow, J., Ives, D., et al. Purification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and 2 expressed in the baculovirus system. Biochim Biophys Acta 1209 130-139 (1994).

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 Med Chem 43 2860-2870 (2000).

Indomethacin N-octyl amide is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

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1 mg 
$19.00

$0.00

5 mg 
$86.00

$0.00

10 mg 
$152.00

$0.00

50 mg 
$665.00

$0.00

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Indomethacin N-octyl amide