Idebenone

Modify Date: 2024-01-02 11:03:32

Idebenone Structure
Idebenone structure
 Common Name Idebenone
CAS Number 58186-27-9 Molecular Weight 338.439
Density 1.1±0.1 g/cm3 Boiling Point 497.3±45.0 °C at 760 mmHg
Molecular Formula C19H30O5 Melting Point 52-550C
MSDS Chinese USA Flash Point 170.1±22.2 °C

 Use of Idebenone


Idebenone is a synthetic variant of coenzyme Q10 (CoQ10), which initially developed for the treatment of Alzheimer's disease and other cognitive defects.Target: OthersIdebenone is a synthetic variant of coenzyme Q10 (CoQ10), which initially developed for the treatment of Alzheimer's disease and other cognitive defects. Idebenone was generally well tolerated with similar numbers of adverse events in each group. One child receiving high-dose idebenone developed neutropenia after 6 months, which resolved after discontinuation of treatment. 8OH2′dG concentrations were not increased, and did not significantly change with idebenone treatment [1]. The 2-year efficacy and safety of idebenone were studied in a prospective, randomized, double-blind multicentre study in 3 parallel groups of patients with dementia of the Alzheimer type (DAT) of mild to moderate degree. A total of 450 patients were randomized to either placebo for 12 months, followed by idebenone 90 mg tid for another 12 months (n = 153) or idebenone 90 mg tid for 24 months (n = 148) or 120 mg tid for 24 months (n = 149). idebenone showed statistically significant dose-dependent improvement in the primary efficacy variable ADAS-Total and in all the secondary efficacy variables [2].

 Names

Name idebenone
Synonym More Synonyms

 Idebenone Biological Activity

Description Idebenone is a synthetic variant of coenzyme Q10 (CoQ10), which initially developed for the treatment of Alzheimer's disease and other cognitive defects.Target: OthersIdebenone is a synthetic variant of coenzyme Q10 (CoQ10), which initially developed for the treatment of Alzheimer's disease and other cognitive defects. Idebenone was generally well tolerated with similar numbers of adverse events in each group. One child receiving high-dose idebenone developed neutropenia after 6 months, which resolved after discontinuation of treatment. 8OH2′dG concentrations were not increased, and did not significantly change with idebenone treatment [1]. The 2-year efficacy and safety of idebenone were studied in a prospective, randomized, double-blind multicentre study in 3 parallel groups of patients with dementia of the Alzheimer type (DAT) of mild to moderate degree. A total of 450 patients were randomized to either placebo for 12 months, followed by idebenone 90 mg tid for another 12 months (n = 153) or idebenone 90 mg tid for 24 months (n = 148) or 120 mg tid for 24 months (n = 149). idebenone showed statistically significant dose-dependent improvement in the primary efficacy variable ADAS-Total and in all the secondary efficacy variables [2].
Related Catalog
References

[1]. Di Prospero, N.A., et al., Neurological effects of high-dose idebenone in patients with Friedreich's ataxia: a randomised, placebo-controlled trial. The Lancet Neurology, 2007. 6(10): p. 878-886.

[2]. Gutzmann, H. and D. Hadler, Sustained efficacy and safety of idebenone in the treatment of Alzheimer's disease: update on a 2-year double-blind multicentre study, in Alzheimer's Disease-From Basic Research to Clinical Applications. 1998, Springer. p. 301-310.

[3]. Lei D, et al. Synergistic neuroprotective effect of rasagiline and idebenone against retinal ischemia-reperfusion injury via the Lin28-let-7-Dicer pathway. Oncotarget. 2018 Jan 30;9(15):12137-12153.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 497.3±45.0 °C at 760 mmHg
Melting Point 52-550C
Molecular Formula C19H30O5
Molecular Weight 338.439
Flash Point 170.1±22.2 °C
Exact Mass 338.209320
PSA 72.83000
LogP 3.49
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.502
Storage condition Room temp

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GU5290000
CHEMICAL NAME :
2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl-
CAS REGISTRY NUMBER :
58186-27-9
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C19-H30-O5
MOLECULAR WEIGHT :
338.49

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10 gm/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Lungs, Thorax, or Respiration - other changes Gastrointestinal - hypermotility, diarrhea
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3931,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
830 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3931,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3931,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3931,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
757 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3931,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3931,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 39,367,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
17500 mg/kg/5W-C
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 13,3955,1985

 Safety Information

Hazard Codes Xi: Irritant;
RIDADR NONH for all modes of transport
RTECS GU5290000

 Synthetic Route

 Articles15

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2-deoxy-D-glucose enhances anesthetic effects in mice.

Anesth. Analg. 120(2) , 312-9, (2015)

The mechanisms of general anesthesia by volatile drugs remain largely unknown. Mitochondrial dysfunction and reduction in energy levels have been suggested to be associated with general anesthesia sta...

Idebenone. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in age-related cognitive disorders.

Drugs Aging 5(2) , 133-52, (1994)

Idebenone is a benzoquinone compound which has been investigated in elderly patients with dementia. Its precise mechanism(s) of action remains unknown, but in vitro and in vivo studies suggest the dru...

Idebenone: an emerging therapy for Friedreich ataxia.

J. Neurol. 256 Suppl 1 , 25-30, (2009)

This paper reviews the history and pre-clinical development of idebenone and summarises the results of clinical studies, published from 1999 to 2008, on the use of idebenone in the treatment of patien...

 Synonyms

6-(10-Hydroxydecyl)ubiquinone
Raxone
Idebenone [INN:JAN]
Daruma
Catena
CV 2619
2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone
Sovrima
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylbenzo-1,4-quinone
Idebenone
Idebenonum [Latin]
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-cyclohexa-2,5-diene-1,4-dione
2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
MFCD00274552
UNII-HB6PN45W4J
2,3-Dimethoxy-5-methyl-6-(10'-hydroxydecyl)-1,4-benzoquinone
2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione
Lucenabol
2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-
Idebenone (JAN)
Mnesis
Avan
Idebenona [Spanish]
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Idebenone Ester
1220282-54-1
Idebenone impurity D
88543-34-4
Idebenone hydroquinone
58186-26-8
idebenone related - 2h-qs4
95233-52-6
Eastman idebenone linoleate
1177393-70-2
Idebenone Sulfate Potassium Salt
319906-76-8
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
849349-65-1
N-[3-(Aminooxy)propyl]-N-butyl-1-butanamine
127437-46-1
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