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Basic information

  • Name:
  • Idebenone

  • CAS No.:
  • 58186-27-9

  • Formula:
  • C19H30O5
  • Synonyms:
  • 2,5-Cyclohexadiene-1,4-dione,2-(10-hydroxydecyl)- 5,6-dimethoxy-3-methyl-;Idebenone (JAN);2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl-;6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone;CV 2619;Idebenone [GMP];2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone;Idebenonum [Latin];Idebenone [INN:JAN];Idebenona [GMP];Idebenona [Spanish];2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-cyclohexa-2,5-diene-1,4-dione;Idenbenone;
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Chemistry

The Molecular Structure of Idebenone (CAS NO.58186-27-9):

Empirical Formula: C19H30O5
Molecular Weight: 338.4385 
IUPAC Name: 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione  
Appearance: Yellow-Orange Crystalline Solid
Nominal Mass: 338 Da
Average Mass: 338.4385 Da
Monoisotopic Mass: 338.209324 Da 
Index of Refraction: 1.502
Molar Refractivity: 92.13 cm3
Molar Volume: 312 cm3
Surface Tension: 41 dyne/cm
Density: 1.08 g/cm3
Flash Point: 170.1 °C
Enthalpy of Vaporization: 88.13 kJ/mol
Boiling Point: 497.3 °C at 760 mmHg 
Melting Point: 52-550 °C
Vapour Pressure: 5.67E-12 mmHg at 25°C 
Storage temp: Room temp
Product Categories: Anthraquinones, Hydroquinones and Quinones;Cnbio;Intermediates & Fine Chemicals;Pharmaceuticals
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
Smiles
C1(=C(C(C(C)=C(C1=O)CCCCCCCCCCO)=O)OC)OC 

History

On July 23, 2008, Health Canada issued a Notice of Compliance under the Notice of Compliance with Conditions (NOC/c) Policy to Santhera Pharmaceuticals (Switzerland) Ltd. for the drug product Catena. The product was authorized under the NOC/c Policy on the basis of the promising nature of the clinical evidence, and the need for a confirmatory study to verify its clinical benefit. Patients should be advised of the fact that the market authorization was issued with conditions.

Uses

 Idebenone (CAS NO.58186-27-9) is a synthetic analogue of coenzyme Q10 used in Europe in the treatment of vascular and degenerative diseases of the central nervous system. It  has been used in the treatment of Friedreich's ataxia and also in topical applications to treat wrinkles.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported > 1gm/kg (1000mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 39, Pg. 367, 1991.
 
mouse LD50 intraperitoneal 757mg/kg (757mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
mouse LD50 oral > 10gm/kg (10000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
rat LD50 intraperitoneal 830mg/kg (830mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
rat LD50 oral 10gm/kg (10000mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985.

Safety Profile

Although studies in animals have shown no harmful effects, this product should not be taken during the first three months of pregnancy and during nursing, only when absolutely necessary and always under a doctor's supervision.
Hazard Codes: IrritantXi
RTECS: GU5290000

Specification

 Idebenone (CAS NO.58186-27-9) is also called as Idebenone [INN:JAN] ; 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone ; Idebenona ; Idebenona [Spanish] ; Idebenone ; Idebenonum ; Idebenonum [Latin] ; 2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl- ; 2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl- ; 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone .It is an organic compound of the quinone family and promoted commercially as a synthetic analog of coenzyme Q10 (CoQ10).

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