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Idebenone

Product Name
Idebenone
CAS No.
58186-27-9
Chemical Name
Idebenone
Synonyms
Idebenon;Idebenone powder;Avan;6-(10-;Daruma;Mnesis;QSA-10;Sovrima;cv 2619;debenone
CBNumber
CB7733840
Molecular Formula
C19H30O5
Formula Weight
338.44
MOL File
58186-27-9.mol
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Idebenone Property

Melting point:
52-550C
Boiling point:
497.3±45.0 °C(Predicted)
Density 
1.08±0.1 g/cm3(Predicted)
storage temp. 
room temp
solubility 
Soluble in DMSO (up to 25 mg/ml).
pka
15.20±0.10(Predicted)
form 
Solid
color 
Orange
Merck 
14,4888
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI
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
InChIKey
JGPMMRGNQUBGND-UHFFFAOYSA-N
SMILES
C1(=O)C(OC)=C(OC)C(=O)C(C)=C1CCCCCCCCCCO
LogP
3.490 (est)
CAS DataBase Reference
58186-27-9(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
WGK Germany 
3
RTECS 
GU5290000
HS Code 
2933399990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I5659
Product name
Idebenone
Purity
≥98% (HPLC)
Packaging
25mg
Price
$173
Updated
2025/07/31
Sigma-Aldrich
Product number
67805
Product name
Idebenone
Purity
analytical standard
Packaging
10mg
Price
$95.6
Updated
2025/07/31
TCI Chemical
Product number
I0848
Product name
Idebenone
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$102
Updated
2025/07/31
TCI Chemical
Product number
I0848
Product name
Idebenone
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$173
Updated
2025/07/31
Cayman Chemical
Product number
15475
Product name
Idebenone
Purity
≥98%
Packaging
10mg
Price
$49
Updated
2024/03/01
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Idebenone Chemical Properties,Usage,Production

Description

Idebenone is an organic compound belonging to the quinone family, being similar to coenzyme Q-10. It is a kind of drug developed by Takeda Pharmaceutical Company for the treatment of Alzheimer’s disease and some other cognitive defects. However, these have been not very much progress associated with this indication. It is now also used for the treatment of Friedreich’s ataxia with a positive effect on cardiac hypertrophy and neurological function. However, this indication is only approved in Canada, not in Europe and US. It is now under investigation on its efficacy for the treatment of Duchenne muscular dystrophy, Leber’s hereditary optic neuropathy, mitochondrial encephalomyopathy, lactic acidosis, and stroke-like episodes) as well as primary progressive multiple sclerosis. The efficacy of this drug still demands more evidences.

Chemical Properties

An odorless yellow-orange crystalline solid. It is highly insoluble in water, but can be easily dissolved in chloroform, methanol, or absolute ethanol. It is also soluble in ethyl acetate, but insoluble in n-hexane.

Originator

Takeda (Japan)

Uses

idebenone is an anti-oxidant capable of protecting the skin from a variety of free-radical attacks, including the formation of secondary chemicals that negatively affect skin physiology. It is said to improve intrinsic as well as extrinsic skin damage caused by freeradical formation. Idebenone is a synthetically manufactured form of coenzyme Q10 and has a smaller molecular structure. This allows it to penetrate the skin and apparently the cellular membrane. Clinical studies demonstrate a visible improvement in photodamaged skin, reduced skin roughness and dryness, decreased fine lines and wrinkles, and increased skin hydration. In addition, idebenone helps improve hyperpigmentation because its molecular structure is similar to that of hydroquinone. Although most of the associated benefits are seen primarily in the epidermis, some increase in dermal collagen has also been confirmed. Idebenone has been used for such health-related problems as Alzheimer’s and heart disease.

Application

Idebenone is ubiquinone derivative with protective effects against cerebral ischemia and cognition enhancer. It has been used:
chemotherapy drug
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

Definition

ChEBI: Idebenone is a member of the class of 1,4-benzoquinones which is substituted by methoxy groups at positions 2 and 3, by a methyl group at positions 5, and by a 10-hydroxydecyl group at positions 6. Initially developed for the treatment of Alzheimer's disease, benefits were modest; it was subsequently found to be of benefit for the symptomatic treatment of Friedreich's ataxia. It has a role as an antioxidant and a ferroptosis inhibitor. It is a primary alcohol and a member of 1,4-benzoquinones.

brand name

AVAN

General Description

Idebenone is a short-chain benzoquinone drug. It is a structural relative of ubiquinone (Coenzyme Q10) that protects the CNS from the effects of ischemia via improving brain metabolism. It is reported to be of potential use in the management of patients with cerebral apoplexy, cerebral arteriosclerosis and related disorders.

Biological Activity

Antioxidant and neuroprotective agent. Protects mitochondrial membranes against lipid peroxidation and blocks glutamate neurotoxicity in vitro and in vivo . Inhibits apoptosis of astrocytes via increased NGF production.

Biochem/physiol Actions

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. A short-chain Coenzyme Q analog that enhances superoxide formation, presumably by mediating electron transfer from N2 to oxygen.

Side effects

The most common adverse reactions to Idebenone are mild to moderate diarrhoea (usually without the need to stop treatment), nasopharyngitis, cough and back pain. The following adverse reactions emerging from clinical trials in LHON patients or reported postmarketing in other indications are tabulated below. Frequency groupings are defined to the following convention: very common (≥1/10), common (≥1/100 to<1/10), not known (cannot be estimated from the available data).

Mode of action

The mechanism of action of idebenone involves its antioxidant properties and ability to act as a mitochondrial electron carrier. Idebenone overcomes mitochondrial complex I respiratory chain deficiency in patients with LHON by transferring electrons directly to mitochondrial complex III (by-passing complex I), thereby restoring cellular energy (ATP) production and re-activating inactive-but-viable retinal ganglion cells, which ultimately prevents further vision loss and promotes vision recovery.
PID27071925

References

[1] ZS.-NAGY I. Chemistry, toxicology, pharmacology and pharmacokinetics of idebenone: a review[J]. Archives of gerontology and geriatrics, 1990, 11 3: Pages 177-186. DOI:10.1016/0167-4943(90)90063-c
[2] GIANLUCA CIVENNI . Inhibitory effect of the neuroprotective agent idebenone on arachidonic acid metabolism in astrocytes[J]. European journal of pharmacology, 1999, 370 2: Pages 161-167. DOI:10.1016/s0014-2999(99)00127-2
[3] KAZUHIRO TAKUMA . CV-2619 protects cultured astrocytes against reperfusion injury via nerve growth factor production[J]. European journal of pharmacology, 2000, 406 3: Pages 333-339. DOI:10.1016/s0014-2999(00)00701-9
[4] ELLEN GERHARDT. Idebenone and resveratrol extend lifespan and improve motor function of HtrA2 knockout mice.[J]. PLoS ONE, 2011: e28855. DOI:10.1371/journal.pone.0028855

Idebenone Preparation Products And Raw materials

Raw materials

Hexane N,N-Dimethylformamide Basic Orange 2 10-acetoxycarbonyl chloride Cresol Potassium Phosphate Monobasic Dichloromethane 3,4,5-Trimethoxytoluene

Preparation Products

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View Lastest Price from Idebenone manufacturers

Jinan Ruitong Biotech Co., Ltd.
Product
Idebenone 58186-27-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1
Release date
2025-09-05
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Idebenone 58186-27-9
Price
US $0.00/Kg/Bag
Min. Order
100g
Purity
98.5%min HPLC
Supply Ability
100KGS
Release date
2021-07-20
Hebei Chuanghai Biotechnology Co., Ltd
Product
Idebenone 58186-27-9
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-24

58186-27-9, IdebenoneRelated Search:

Methyl acrylate Diphenyldimethoxysilane Methylparaben Kresoxim-methyl Bensulfuron methyl Methyltriethoxysilane 1,4-Benzoquinone Methyltrimethoxysilane Dimethyldimethoxysilane 1,1-Dimethoxyethane Methyl Methyl bromide p-Toluquinone METHOXYBENZOQUINONE 2,3-Dimethoxy-5-methyl-p-benzoquinone PRIMIN Parathion-methyl 1,4-HEXADIENE

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