基本情報
- CAS
1189907-75-2- 標準SMILES
COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O- InChIKey
JGPMMRGNQUBGND-UHFFFAOYSA-N- 分子式
- C19H30O5
- 平均分子量
- 338.4 g/mol
概要
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 a ferroptosis inhibitor and an antioxidant. It is a member of 1,4-benzoquinones and a primary alcohol.
名称と識別子
- 優先名称
- Idebenone
- IUPAC
- 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
- 英語名
- Mnesis-13C,d3
- 分子式
- C19H30O5
- 分子量
- 338.4385
名称と別名
idebenone58186-27-9IdebenonaRaxone2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dioneIdebenonumSovrimaCV 2619hydroxydecyl ubiquinoneCV-2619Oristar hdu2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone
名称をさらに表示
Avan-13C,d3Mnesis-13C,d3DaruMa-13C,d3CV 2619-13C,d3Idebenone-13C,d32,3-DiMethoxy-6-(10-hydroxydecyl)-5-Methyl-1,4-benzoquinone-13C,d32-(10-Hydroxydecyl)-6-Methoxy-5-(Methoxy-13C,d3)-3-Methyl-2,5-cyclohexadiene-1,4-dione2-(10-hydroxydecyl)-6-methoxy-3-methyl-5-(trideuteriomethoxy)cyclohexa-2,5-diene-1,4-dione
DTXSID00406786-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinoneHB6PN45W4JCHEBI:31687NSC-7592282-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-DTXCID8020678
データベース識別子
- CAS
1189907-75-2
物性
構造計算による物性
- XLogP
- 4.3
- 極性表面積
- 72.8 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 12
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 502
実験および物理化学的性質
CosmeticsCosmetic ingredients (Hydroxydecyl Ubiquinone) -> CIR (Cosmetic Ingredient Review)
LogP2.96
Human DrugsEMA approved medicines: Human medicine
Collision Cross Section
173.7 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
178.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 48 · 48-50°C
- 貯蔵温度
- -20 °C · Amber Vial, -20°C Freezer, Under Inert Atmosphere
- 溶解性
- Chloroform (Sparingly), Hexanes (Slightly, Heated, Sonicated), Methanol (Slightly)
- 外見
- 個体
- 色
- オレンジ低融点
- 安定性
- 光に敏感
化学的性質
化学的特性Orange Solid
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 25% (1 of 4) of reports.
Danger
H228 (25%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesFlam. Sol. 2 (25%)
毒性情報
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
化学と産業
薬理情報
ATC Code
N06BX13
N - Nervous system
QN - Nervous system
Mechanism of Action
Idebenone is a synthetic analogue of ubiquinone (also known as Coenzyme Q10), a vital cell antioxidant and essential component of the Electron Transport Chain (ETC). It has been proposed that by interacting with the ETC, idebenone increases ATP production required for mitochondrial function, reduces free radicals, inhibits lipid peroxidation, and consequently protects the lipid membrane and mitochondria from oxidative damage. More specifically, idebenone is thought to transfer electrons directly to complex III of the mitochondrial ETC, thereby circumventing complex I and restoring cellular energy (ATP) generation.
Metabolism/Metabolites
Metabolism occurs by means of oxidative shortening of the side chain and by reduction of the quinone ring and conjugation to glucuronides and sulphates. Idebenone shows a high first pass metabolism resulting in conjugates of idebenone (glucuronides and sulphates (IDE-C)) and the Phase I metabolites QS10, QS6, and QS4 as well as their corresponding Phase II metabolites (glucuronides and sulphates (QS10+QS10-C, QS6+QS6-C, QS4+QS4-C)). The main metabolites in plasma are IDE-C and QS4+QS4-C.
MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Absorption, Distribution and Excretion
After oral administration, idebenone is rapidly absorbed. On repeat dosing, maximum plasma concentrations of idebenone are reached on average within 1 hour (median 0.67 h range: 0.33-2.00 h). Food increases the bioavailability of idebenone by approximately 5-7-fold and i therefore should always be administered with food.
The main route of elimination is metabolism, with the majority of dose excreted via the kidneys as metabolites. After a single or repeated oral dose of 750 mg of idebenone, QS4+QS4-C were the most prominent idebenone-derived metabolites in urine, representing on average between 49.3% and 68.3% of the total administered dose. QS6+QS6 represented 6.45% to 9.46%, whereas QS10+QS10-C and IDE+IDE-C were close to 1% or below.
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