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Merck
CN

I5659

Idebenone

≥98% (HPLC), powder

Synonym(s):

2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

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About This Item

Empirical Formula (Hill Notation):
C19H30O5
CAS Number:
58186-27-9
Molecular Weight:
338.44
UNSPSC Code:
12352204
PubChem Substance ID:
329815386
NACRES:
NA.25
MDL number:
MFCD00274552

Key Documents

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Product Name

Idebenone, ≥98% (HPLC)

SMILES string

O=C(C(OC)=C1OC)C(CCCCCCCCCCO)=C(C)C1=O

InChI key

JGPMMRGNQUBGND-UHFFFAOYSA-N

InChI

1S/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3

assay

≥98% (HPLC)

form

powder

solubility

methanol: 50 mg/mL, clear to slightly hazy

storage temp.

room temp

Quality Level

200

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General description

Idebenone is a short-chain benzoquinone drug.

Application

Idebenone has been used:
  • to treat mutant myocilin (mMYOC) cells for drug treatment assay
  • to validate C2C12 secondary cell screening assay
  • to treat obese mice, to test whether idebenone and CoQ10 bind directly to peroxisome proliferator-activated receptor (PPAR)LBDs, His-tagged PPARα, δ and γ LBDs

Biochem/physiol Actions

A short-chain Coenzyme Q analog that enhances superoxide formation, presumably by mediating electron transfer from N2 to oxygen.
Idebenone is used in the treatment of visual impairment in adolescents and adults with Leber′s hereditary optic neuropathy (LHON). It serves as an antioxidant. It helps to guard the heart muscle against oxidative stress.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000468735
0000468735
0000446389
0000446389
0000429846

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L Montenegro et al.
Journal of nanoscience and nanotechnology, 12(1), 330-337 (2012-04-25)
The aim of this study was to evaluate in vitro the permeation of the antioxidant agent Idebenone (IDE) loaded into solid lipid nanoparticles (SLN) across MDCKII-MDR1 cell monolayer, selected as an in vitro model of the Blood Brain Barrier (BBB).
Oliver Gamondi et al.
Drug metabolism letters, 6(2), 120-123 (2012-09-15)
We investigated the damage caused by oxidative stress using the yeast Saccharomyces cerevisiae as a model biological system. After inducing oxidative stress with menadione, we were able to evaluate the extent of cellular oxidative stress by utilizing 2',7'-dichlorofluorescein diacetate (DCFH-DA)
Carolyn P Ojano-Dirain et al.
The Laryngoscope, 122(11), 2543-2548 (2012-09-12)
Antioxidants have been shown to protect against aminoglycoside-induced hearing loss. Mitoquinone (MitoQ) is a mitochondria-targeted derivative of the antioxidant ubiquinone. MitoQ is attached to a lipophilic triphenylphosphonium (TPP) cation, which enables its accumulation inside the mitochondria several hundred-fold over the
Idebenone: a review in Leber?s hereditary optic neuropathy
Lyseng-Williamson KA
Drugs, 76(7), 805-813 (2016)
Persistence of the treatment effect of idebenone in Leber's hereditary optic neuropathy.
T Klopstock et al.
Brain : a journal of neurology, 136(Pt 2), e230-e230 (2013-02-08)
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