58186-27-9 Usage
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
Yellow-Orange Crystalline Solid, odorless. Extremely insoluble in water, easily soluble in chloroform, methanol or absolute ethanol, easily soluble in ethyl acetate, and 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.
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.
Application
Idebenone is ubiquinone derivative with protective effects against cerebral ischemia and cognition enhancer. It has been used:chemotherapy drugto treat mutant myocilin (mMYOC) cells for drug treatment assayto validate C2C12 secondary cell screening assayto 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
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.
References
1) Zs-Nagy (1990) Chemistry, toxicology, pharmacology and pharmacokinetics of idebenone: a review; Gerontol. Geriatr., 11, 1772) Civenni et al. (1999) Inhibitory effect of the neuroprotetive agent idebenone on arachidonic acid metabolism in astrocytes; Eur. J. Pharmacol., 370 1613) Takuma et al. (2000) CV-2619 protects cultured astrocytes against reperfusion injury via nerve growth factor production; Eur. J. Pharmacol., 406 3334) Gerhardt et al. (2011) Idebenone and resveratrol extend lifespan and improve motor function of HtrA2 knockout mice; PloS One, 6 e28855
Check Digit Verification of cas no
The CAS Registry Mumber 58186-27-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,1,8 and 6 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 58186-27:
(7*5)+(6*8)+(5*1)+(4*8)+(3*6)+(2*2)+(1*7)=149
149 % 10 = 9
So 58186-27-9 is a valid CAS Registry Number.
InChI:InChI=1/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
58186-27-9Relevant articles and documents
AgNO3-catalyzed decarboxylative cross-coupling reaction: an approach to coenzyme Q
Luo, Wan-Yue,Lu, Bin,Qiu, Yong-Fu,Zhou, Rong-Ye,He, Yong-Jing,Wang, Jin
, p. 8702 - 8704 (2020)
An efficient and general method for the synthesis of coenzyme Q compounds through the activation of the 1,4-benzoquinone Csp2-H bond has been developed. This C-C bond formation reaction proceeds readily in an open flask by the direct cross-coupling reaction of coenzyme Q0with commercially available aliphatic carboxylic acids utilizing AgNO3as a catalyst and K2S2O8as an oxidant in aqueous solution. This radical reaction is operationally simple and amenable to gram-scale synthesis.
Coenzyme Q compound synthesis method
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Paragraph 0037, (2020/11/01)
The invention relates to a coenzyme Q compound synthesis method, which comprises the steps of: dissolving substituted or unsubstituted 3, 4, 5-trimethoxytoluene in an organic solvent, carrying out a reaction on the obtained solution and an oxidant aqueous solution for 1-2h at a temperature of 20-80 DEG C under the catalysis of an acid, and carrying out extraction, water washing, reduced pressure distillation and recrystallization on the obtained crude product to obtain a coenzyme Q compound. Raw materials used in the method are cheap and easy to obtain, and no toxic or harmful waste gas or waste residue is generated in the reaction process; and reaction steps are few, the operation is easy and convenient, the product yield is high, and the method is suitable for industrial large-scale production.
A preparation method of idebenone (by machine translation)
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Paragraph 0021; 0024; 0026; 0028; 0030; 0032; 0034, (2017/09/01)
The invention relates to a preparation method of idebenone, the method comprises: to coenzyme Q0 and 11 - hydroxy undecanoic acid as the raw material, the choice of copper chloride, copper sulfate, copper acetate, silver carbonate, silver oxide, palladium chloride or palladium acetate in a metal salt as a catalyst, in the protection of the next adds oxygen oxidizing agent hydrogen peroxide, alkylation of the free radical reaction. The reaction system by extraction, water washing, drying, reduced pressure distillation, column chromatography, get the yellow needle-like crystal, 6 - (10 - hydroxyl decyl) - 2, 3 - dimethoxy - 5 - methyl - 1, 4 - benzoquinone, namely idebenone. This preparation method has a simple operation, low cost, and the yield and the like, suitable for large-scale industrial production of idebenone. (by machine translation)
