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艾地苯醌

艾地苯醌用途

Idebenone是合成的辅酶Q10的变体,最初用于阿尔茨海默症和其它的认知缺陷。

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艾地苯醌名称

[ CAS 号 ]:
58186-27-9

[ 中文名 ]:
艾地苯醌

[ 英文名 ]:
Idebenone

[中文别名 ]:

艾地苯

[英文别名 ]:

6-(10-Hydroxydecyl)ubiquinone
Raxone
Idebenone [INN:JAN]
Daruma
Catena
CV 2619
Sovrima
Idebenone
Idebenonum [Latin]
MFCD00274552

艾地苯醌生物活性

[ 描述 ]:

Idebenone是合成的辅酶Q10的变体,最初用于阿尔茨海默症和其它的认知缺陷。

[ 相关类别 ]:

信号通路 >> 其他 >> 其他

天然产物 >> 醌类

研究领域 >> 神经疾病

[参考文献]

[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.

[相关活性小分子]

艾地苯醌物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
497.3±45.0 °C at 760 mmHg

[ 熔点 ]:
52-550C

[ 分子式 ]:
C₁₉H₃₀O₅

[ 分子量 ]:
338.439

[ 闪点 ]:
170.1±22.2 °C

[ 精确质量 ]:
338.209320

[ PSA ]:
72.83000

[ LogP ]:
3.49

[ 外观性状 ]:
从石油醚得橙色针状结晶，熔点46~50℃。从己烷-乙酸乙酯得结晶，熔点52~53℃。极易溶于氯仿、甲醇或无水乙醇，易溶于乙酸乙酯，溶于多数有机溶剂，难溶于正己烷，几不溶于水。

[ 蒸汽压 ]:
0.0±2.9 mmHg at 25°C

[ 折射率 ]:
1.502

[ 储存条件 ]:
Room temp

[ 水溶解性 ]:
水溶性：不溶；微溶：甲醇

艾地苯醌MSDS

详细MSDS(安全技术说明书)

艾地苯醌毒性和生态

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

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艾地苯醌安全信息

[ 危害码 (欧洲) ]:
Xi: Irritant;

[ 危险品运输编码 ]:
NONH for all modes of transport

[ RTECS号 ]:
GU5290000

艾地苯醌合成路线

详细合成路线

艾地苯醌上下游产品

艾地苯醌上游产品

艾地苯醌下游产品

艾地苯醌制备

方法1：3，4，5-三甲氧基甲苯、10-乙酰氧基癸酰氯和三氯化铝在二氯乙烷中，冰浴冷却搅拌2h，再室温搅拌70h。倾入冰水，二氯甲烷提取，水洗，干燥。蒸除溶剂，得浅棕色油状的6-(10-乙酰氧基-1-氧代癸基)-2，3-二甲氧基-5-甲基苯酚。然后加入甲醇和氢氧化钠，室温搅拌2h。蒸除溶剂，加入水，用盐酸调至Ph值3。过滤析出的结晶，真空干燥。粗品溶于氯仿，用硅胶柱分离，先用氯仿-甲醇(95：5)洗脱杂质，再用氯仿-甲醇(90：10)洗脱，收集所需组分，蒸去溶剂，用乙醚-己烷(1：3)重结晶，得白色结晶的6-(10-羟基-1-氧代癸基)-2，3-二甲氧基-5-甲基苯酚，熔点66.5~68℃，收率63.1%(以3，4，5-三甲氧基甲苯计)。上述产物和醋酸、5%Pd-C及70%高氯酸一起，于室温常压加氢20h以上。滤除催化剂后浓缩，加人二氯甲烷，用5%碳酸氢钠洗涤2次，干燥。蒸除溶剂得浅色油状的6-(10-羟基癸基)-2，3-二甲氧基-5-甲基苯酚，收率95%。该油状物和新制备的弗瑞麦盐(Frerny’s salt)、二甲基甲酰胺-水-甲醇(1：1：1)和小量的磷酸二氢钾于50℃搅拌7h。反应完全后加水稀释，用二氯甲烷提取，水洗2次，干燥。蒸除溶剂，用正己烷-乙醚(3：1)重结晶，得橘红色针状结晶的艾地苯醌，熔点54~55℃．收率69.6%。

方法2：3，4，5-三甲氧基甲苯和癸二酸单乙酯的酰氯，在三氯化铝催化下进行酰化反应，在2位酰化，再水解。然后还原生成10-(2-羟基-3，4-二甲氧基-6-甲基苯基)癸酸，接着氧化为醌，乙酯化再还原酯基为羟基而得艾地苯醌。和方法1的区别仅在于先氧化为醌，而后还原侧链，操作方法和方法1均相似。

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艾地苯醌文献

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...

更多文献

艾地苯醌

艾地苯醌用途

艾地苯醌名称

艾地苯醌生物活性

艾地苯醌物理化学性质

艾地苯醌MSDS

详细MSDS(安全技术说明书)

艾地苯醌毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

艾地苯醌安全信息

艾地苯醌合成路线

详细合成路线

艾地苯醌上下游产品

艾地苯醌上游产品

艾地苯醌下游产品

艾地苯醌制备

艾地苯醌文献

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