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5.34032

Sigma-Aldrich

NOX Inhibitor IV, GKT136901

Synonym(s):

NOX Inhibitor IV, GKT136901, 2-(2-Chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo-[4,3-c]pyridine-3,6(2H,5H)-dione, NADPH Oxidase Inhibitor IV, Dual NOX4/NOX1 Inhibitor, GKT-136901

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About This Item

Empirical Formula (Hill Notation):
C19H15ClN4O2
CAS Number:
955272-06-7
Molecular Weight:
366.80
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

pale yellow to brown

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

InChI

1S/C19H15ClN4O2/c1-12-18-15(10-17(25)23(12)11-13-6-4-5-9-21-13)22-24(19(18)26)16-8-3-2-7-14(16)20/h2-10,22H,11H2,1H3

InChI key

DNKYHHFCPXKFIY-UHFFFAOYSA-N

General description

An orally bioavailable, non-toxic pyrazolopyridinedione based compound that acts as a potent and reversible inhibitor of NOX1- and NOX4-containing NADPH oxidase activity (Ki = 160 and 165 nM, respectively, Amplex Red assay) and devoid of antioxidant properties. At higher concentrations, affects NOX2 (Ki = 1.53 uM). Blocks NOX-mediated ROS (reactive oxygen species) outburst in NOX isozyme expressing PMN cell membranes. Exhibits poor affinity towards xanthine oxidase, lipoxygenases-5/12, myeloperoxidase, MAO-B, iNOS and eNOS, several cytochrome P450 isozymes, PTP1B and a panel containing representative ion-channels and kinases at 10 µM. Functions as a selective scavenger of peroxynitrite over nitric oxide, superoxide radical anion and hydroxyl radical.
An orally bioavailable, non-toxic pyrazolopyridinedione based compound that acts as a potent and reversible inhibitor of NOX1- and NOX4-containing NADPH oxidase activity (Ki = 160 and 165 nM, respectively, Amplex Red assay) and devoid of antioxidant properties. At higher concentrations, affects NOX2 (Ki = 1.53 uM). Blocks NOX-mediated ROS (reactive oxygen species) outburst in NOX isozyme expressing PMN cell membranes. Exhibits poor affinity towards xanthine oxidase, lipoxygenases-5/12, myeloperoxidase, MAO-B, iNOS and eNOS, several cytochrome P450 isozymes, PTP1B and a panel containing representative ion-channels and kinases at 10 µM. Functions as a selective scavenger of peroxynitrite over nitric oxide, superoxide radical anion and hydroxyl radical.

Please note that the molecular weight for this compound is batch-specific due to variable water content. Please refer to the vial label or the certificate of analysis for the batch-specific molecular weight. The molecular weight provided represents the baseline molecular weight without water.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
NOX1- and NOX4-containing NADPH oxidase activity
Reversible: yes

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
Use only fresh DMSO for reconstitution.

Other Notes

Schildknecht, S., et al. 2014. Curr. Med. Chem.21, 365.
Laleu, B., et al. 2010. J. Med. Chem.53, 7715.
Sedeek, M., et al. 2010. Am. J. Physiol. Renal Physiol.299, F1348.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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