Indomethacin with enhanced selectivity for COX-2
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Indomethacin N-octyl amide

Item No. 70273

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-octyl-1-(4-chlorobenzoyl)-5-methoxy-1H-indole-3-acetamide
CAS Number
282728-65-8
Molecular Formula
C27H33ClN2O3
Formula Weight
469.0
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 27 mg/mlDMF:PBS (5:2): 8 mg/mlEthanol: 2 mg/ml
λmax
230, 260, 319 nm
SMILES
ClC1=CC=C(C(N2C(C=CC(OC)=C3)=C3C(CC(N([H])CCCCCCCC)=O)=C2C)=O)C=C1
InChi Code
InChI=1S/C27H33ClN2O3/c1-4-5-6-7-8-9-16-29-26(31)18-23-19(2)30(25-15-14-22(33-3)17-24(23)25)27(32)20-10-12-21(28)13-11-20/h10-15,17H,4-9,16,18H2,1-3H3,(H,29,31)
InChi Key
DBWILLAXKDUAPA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(1), 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(15), 2860-2870 (2000).