Idebenone

HCID 3686CAS 58186-27-9

Basic information

Standard SMILES
COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O
InChIKey
JGPMMRGNQUBGND-UHFFFAOYSA-N
Molecular formula
C19H30O5
Average molar mass
338.4 g/mol
Monoisotopic mass
338.20932405

Names & identifiers

Preferred name
Idebenone
IUPAC
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
English name
Idebenone
Molecular formula
C19H30O5
Molecular weight
338.44

Names & synonyms

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
Show more names
IdebenonAvandebenoneIdebenone powder6-(10-DarumaMnesisQSA-10
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

Database identifiers

CAS
58186-27-9
PubChem CID
3686
DTXSID
DTXSID0040678
ChEMBL
CHEMBL252556
ChEBI
CHEBI:31687
UNII
HB6PN45W4J
EC Number
814-253-7
Nikkaji
J22.706D

Properties

Computed structural properties

XLogP
4.3
Topological polar surface area
72.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
12
Heavy atoms
24

Experimental & physicochemical properties

Collision Cross Section · 2 items

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]

Physicochemical properties

Melting point
52 · 52-550C
Boiling point
497.3 · 497.3±45.0 °C(Predicted)
Density
1.08 · 1.08±0.1 g/cm3(Predicted)
storage temp.
room temp
solubility
Soluble in DMSO (up to 25 mg/ml).
pka
15.2 · 15.20±0.10(Predicted)

Safety & regulation

GHS classification

GHS Classification · 6 items

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.

Hazard information

Hazard Classes and CategoriesFlam. Sol. 2 (25%);Acute Tox. 4 (25%);Skin Irrit. 2 (25%);Eye Irrit. 2A (25%);STOT SE 3 (25%)

Toxicology

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

Safety data

wgk
3
rtecs
GU5290000
hs_code
2933399990
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi

Chemistry & industry

Pharmacology

ATC Code · 3 items

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 · 1 item

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 · 1 item

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 · 3 items

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.

Uses & manufacturing

UsesCIR ingredient: Hydroxydecyl Ubiquinone
Applications · 3 items

DescriptionIdebenone 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.

Usesidebenone 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.

General DescriptionIdebenone 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.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海沛灵生物科技有限公司13127581762 13127581762 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

38 records

Linked notes

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