An active metabolite of dronedarone
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Parent Compound(s)
9000543Dronedarone (hydrochloride)
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N-Desbutyl Dronedarone (hydrochloride)

Item No. 34888

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-butyl-3-[4-[3-(butylamino)propoxy]benzoyl]-5-benzofuranyl]-methanesulfonamide, monohydrochloride
CAS Number
197431-02-0
Molecular Formula
C27H36N2O5S • HCl
Formula Weight
537.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:6): 0.14 mg/mlEthanol: 1 mg/ml
λmax
218, 250, 291 nm
SMILES
O=C(C1=C(CCCC)OC2=CC=C(NS(C)(=O)=O)C=C21)C3=CC=C(C=C3)OCCCNCCCC.Cl
InChi Code
InChI=1S/C27H36N2O5S.ClH/c1-4-6-9-25-26(23-19-21(29-35(3,31)32)12-15-24(23)34-25)27(30)20-10-13-22(14-11-20)33-18-8-17-28-16-7-5-2;/h10-15,19,28-29H,4-9,16-18H2,1-3H3;1H
InChi Key
ZDXBTJLIQYUYSZ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    25 mg

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    Product Description

    N-Desbutyl dronedarone is an active metabolite of the antiarrhythmic agent dronedarone (Item No. 9000543).1,2,3 It is formed from dronedarone by cytochrome P450s (CYPs) and monoamine oxidase (MAO) in human hepatocyte preparations.4 N-Desbutyl dronedarone inhibits the binding of 3,3',5-triiodo-L-thyronine (T3; Item No. 16028) to the thyroid hormone receptors TRα1 and TRβ1 (IC50s = 59 and 280 µM for the chicken and human receptors, respectively).1 It inhibits CYP2J2-mediated formation of 14,15-EET from arachidonic acid and soluble epoxide hydrolase-mediated formation of 14,15-DHET from 14,15-EET (IC50s = 1.59 and 2.73 µM, respectively, in cell-free assays).2 N-Desbutyl dronedarone decreases intracellular ATP levels in H9c2 rat cardiomyocytes (IC50 = 1.07 µM) and inhibits mitochondrial complex I, also known as NADH dehydrogenase, and mitochondrial complex II, also known as succinate dehydrogenase, activities in isolated rat heart mitochondria (IC50s = 11.94 and 24.54 µM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Van Beeren, H.C., Jong, W.M.C., Kaptein, E., et al. Dronerarone acts as a selective inhibitor of 3,5,3'-triiodothyronine binding to thyroid hormone receptor-α1: in vitro and in vivo evidence. Endocrinology 144(2), 552-558 (2003).

    2. Karkhanis, A., Tram, N.D.T., and Chan, E.C.Y. Effects of dronedarone, amiodarone and their active metabolites on sequential metabolism of arachidonic acid to epoxyeicosatrienoic and dihydroxyeicosatrienoic acids. Biochem. Pharmacol. 146, 188-198 (2017).

    3. Karkhanis, A., Leow, J.W.H., Hagen, T., et al. Dronedarone-induced cardiac mitochondrial dysfunction and its mitigation by epoxyeicosatrienoic acids. Toxicol. Sci. 163(1), 79-91 (2018).

    4. Klieber, S., Arabeyre-Fabre, C., Moliner, P., et al. Identification of metabolic pathways and enzyme systems involved in the in vitro human hepatic metabolism of dronedarone, a potent new oral antiarrhythmic drug. Pharmacol. Res. Perspec. 2(3), e00044 (2014).