Indomethacin heptyl ester

Cayman Chemical Item Number 70271

Indomethacin heptyl ester

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 derivatized as an ester or amide. These derivatives show enhanced selectivity for the COX-2 isoform. For example, the IC₅₀ for indomethacin heptyl ester for the inhibition of human recombinant COX-2 is 0.04 µM, making it more than 1,700 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.²

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

1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid, 1-heptyl ester

Molecular Formula

C₂₆H₃₀ClNO₄

Formula Weight

456.0

Formulation

A solution in methyl acetate

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(OCCCCCCC)=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 heptyl ester is available in the following screening library:

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

Size

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Subtotal

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 heptyl ester