基本情報
- 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
- 単同位体質量
- 338.20932405
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
- 現地名
- イデベノン
- 英語名
- Idebenone
- 分子式
- C19H30O5
- 分子量
- 338.44
名称と別名
名称をさらに表示
データベース識別子
- CAS
58186-27-9- PubChem CID
- 3686
- DTXSID
DTXSID0040678- ChEMBL
CHEMBL252556- ChEBI
CHEBI:31687- UNII
- HB6PN45W4J
- EC Number
- 814-253-7
- Nikkaji
- J22.706D
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
Collision Cross Section
173.7 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];181.56 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];181.21 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];175.92 Ų [M+H]+ [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
- 52 · 52-550C
- 沸点
- 497.3 · 497.3±45.0 °C(Predicted)
- 比重(密度)
- 1.08 · 1.08±0.1 g/cm3(Predicted)
- 貯蔵温度
- room temp
- 溶解性
- DMSO に可溶 (最大 25 mg/ml)。
- 酸解離定数(Pka)
- 15.2 · 15.20±0.10(Predicted)
- 外見
- Solid
- 色
- オレンジ
- Merck
- 14 · 14,4888
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 3 か月間保存できます。
- 化粧品成分の機能
- 抗酸化物質
- 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
- 3.49 · 3.490 (est)
- CAS データベース
- 58186 · 58186-27-9(CAS DataBase Reference)
化学的性質
化学的特性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.
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];H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (25%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
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.;Reported as not meeting GHS hazard criteria per 1 of 4 reports by companies.;There are 3 notifications provided by 3 of 4 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
毒性情報
安全データ
- wgk
- 3
- rtecs
- GU5290000
- hs_code
- 2933399990
- hazard_code
- Xi
化学と産業
薬理情報
ATC Code
N06BX13
N - Nervous system;N06 - Psychoanaleptics;N06B - Psychostimulants, agents used for adhd and nootropics;N06BX - Other psychostimulants and nootropics;N06BX13 - Idebenone
QN - Nervous system;QN06 - Psychoanaleptics;QN06B - Psychostimulants, agents used for adhd and nootropics;QN06BX - Other psychostimulants and nootropics;QN06BX13 - Idebenone
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.
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.
Experimental data have shown that idebenone passes the blood-brain barrier and is distributed at significant concentrations in cerebral tissue. Following oral administration pharmacologically relevant concentrations of idebenone are detectable in the aqueous humor of the eye.
用途と製造
応用分野
用途薬理研究用。
説明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.
使用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.
一般的な説明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.
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義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.
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