CAS 58186-27-9|Idebenone

Introduction：Basic information about CAS 58186-27-9|Idebenone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Idebenone BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles15
7. Synonyms

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	ChineseUSA	Flash Point	170.1±22.2 °C

Names

Name	idebenone
Synonym	More Synonyms

Idebenone BiologicalActivity

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	Signaling Pathways >>Others >>OthersNatural Products >>QuinonesResearch Areas >>Neurological Disease
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.

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

Signaling Pathways >>Others >>OthersNatural Products >>QuinonesResearch Areas >>Neurological Disease

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
InChIKey	JGPMMRGNQUBGND-UHFFFAOYSA-N
SMILES	COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O
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

Articles15

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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