Idebenone
[CAS# 58186-27-9]

Identification

• Classification: API >> Nervous system medication >> Brain metabolism regulating drug
• Name: Idebenone
• Synonyms: 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-cyclohexa-2,5-diene-1,4-dione; CV 2619
• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.44
• CAS Registry Number: 58186-27-9
• EC Number: 814-253-7
• SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCCO

Properties

• Solubility: 11.48 mg/L (25 °C water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.502, Calc.^*
• Melting point: 192.68 °C
• Boiling Point: 497.3±45.0 °C (760 mmHg), Calc.^*, 463.43 °C
• Flash Point: 170.1±22.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H228-H315-H319-H335
• Safety Statements: P210-P240-P241-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Flammable solids	Flam. Sol.	2	H228
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Idebenone, also known as 2,3-dimethoxy-5-methyl-6-(10-hydroxydecyl)-1,4-benzoquinone, is a drug derived from coenzyme Q10 (ubiquinone) A synthetic compound, Coenzyme Q10 is a naturally occurring substance. Idebenone was first synthesized in Japan in the 1980s by Takeda Pharmaceuticals. Initially studied for its potential neuroprotective properties, its antioxidant and anti-aging effects were later explored.

The neuroprotective properties of idebenone have been extensively studied. It is thought to enhance cellular energy metabolism and improve mitochondrial function, thereby protecting neurons from damage and promoting their survival. Idebenone has shown promise in preclinical models of neurodegenerative diseases such as Alzheimer's, Parkinson's and Huntington's diseases, as well as stroke and traumatic brain injury. Idebenone has been studied as a potential treatment for mitochondrial diseases. Mitochondrial diseases can present with a variety of clinical symptoms, including muscle weakness, fatigue, cognitive impairment, and organ dysfunction. Idebenone has been shown to improve mitochondrial function, increase cellular ATP production, and reduce symptoms in patients with mitochondrial diseases, such as Leber's hereditary optic neuropathy (LHON) and Friedreich's ataxia. Idebenone has potent antioxidant activity, scavenging free radicals and reactive oxygen species (ROS) that cause oxidative damage and cellular senescence. Its antioxidant properties help protect cells and tissues from damage caused by oxidative stress, inflammation and DNA damage. Idebenone is widely used in skin care products for its anti-aging properties and ability to combat signs of skin aging such as fine lines, wrinkles and uneven pigmentation. It acts as a powerful antioxidant and helps protect skin from environmental stressors, UV radiation and oxidative damage. Idebenone is incorporated into cosmeceutical formulations, including anti-aging creams, serums and moisturizers, as a key active ingredient that promotes skin health and vitality. Idebenone is also marketed as a dietary supplement. It is often promoted as a nootropic or ""smart drug"" that can improve cognitive function, memory, and mental clarity. However, further research is needed to fully elucidate its cognitive effects and safety in humans.

References

2015. Cellular interactions and photoprotective effects of idebenone-loaded nanostructured lipid carriers stabilized using PEG-free surfactant. International Journal of Pharmaceutics, 479(1).
DOI: 10.1016/j.ijpharm.2014.12.044

2010. Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria. Bioorganic & Medicinal Chemistry, 18(17).
DOI: 10.1016/j.bmc.2010.06.104

1994. Idebenone. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in age-related cognitive disorders. Drugs & Aging, 5(2).
DOI: 10.2165/00002512-199405020-00007