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地丹诺辛

地丹诺辛用途

Didanosine(Videx)是逆转录酶抑制剂,IC50为490nM。

地丹诺辛名称

[ CAS 号 ]:
69655-05-6

[ 中文名 ]:
地丹诺辛

[ 英文名 ]:
2',3'-Dideoxyinosine

[中文别名 ]:

[英文别名 ]:

DDI
Videx
MFCD00077728
Inosine, 2’,3’-dideoxy-
VIDEX EC
2',3'-Dideoxyinosine
INOSINE, 2',3'-DIDEOXY-
Dideoxyinosine
Didanosine
didanosinum [INN_la]

地丹诺辛生物活性

[ 描述 ]:

Didanosine(Videx)是逆转录酶抑制剂,IC50为490nM。

[ 相关类别 ]:

信号通路 >> 抗感染 >> HIV

信号通路 >> 抗感染 >> 逆转录酶

研究领域 >> 感染

[参考文献]

[1]. Knupp, C.A., et al., Pharmacokinetics of didanosine in patients with acquired immunodeficiency syndrome or acquired immunodeficiency syndrome-related complex. Clin Pharmacol Ther, 1991. 49(5): p. 523-35.

[2]. Bissuel, F., et al., Fulminant hepatitis with severe lactate acidosis in HIV-infected patients on didanosine therapy. J Intern Med, 1994. 235(4): p. 367-71.

[相关活性小分子]

地丹诺辛物理化学性质

[ 密度 ]:
1.8±0.1 g/cm3

[ 沸点 ]:
531.2±60.0 °C at 760 mmHg

[ 熔点 ]:
193-195 °C

[ 分子式 ]:
C₁₀H₁₂N₄O₃

[ 分子量 ]:
236.227

[ 闪点 ]:
275.0±32.9 °C

[ 精确质量 ]:
236.090942

[ PSA ]:
93.03000

[ LogP ]:
-1.31

[ 外观性状 ]:
白色结晶粉末

[ 蒸汽压 ]:
0.0±1.5 mmHg at 25°C

[ 折射率 ]:
1.798

[ 储存条件 ]:
2-8°C

[ 稳定性 ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

[ 水溶解性 ]:
1-5 g/100 mL at 21 ºC

地丹诺辛MSDS

地丹诺辛毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM7460700

CHEMICAL NAME :: Inosine, 2',3'-dideoxy-

CAS REGISTRY NUMBER :: 69655-05-6

LAST UPDATED :: 199803

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C10-H12-N4-O3

MOLECULAR WEIGHT :: 236.26

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 2340 mg/kg/34W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Liver - jaundice, cholestatic Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 28 gm/kg/28D-I

TOXIC EFFECTS :: Immunological Including Allergic - decrease in humoral immune response

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 6 gm/kg/3D (Intermittent)

REFERENCE :: EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 18,168,1991

地丹诺辛安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
C

[ 风险声明 (欧洲) ]:
R34

[ 安全声明 (欧洲) ]:
S26-S27-S36/37/39-S45

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

[ WGK德国 ]:
2

[ RTECS号 ]:
NM7460700

[ 海关编码 ]:
2942000000

地丹诺辛合成路线

地丹诺辛上下游产品

地丹诺辛上游产品

地丹诺辛下游产品

地丹诺辛制备

方法1：肌苷(I，15.0g，56mmo1)和咪唑悬浮于二甲基甲酰胺中，在搅拌下加入叔丁基氯化硅，再搅拌20h。减压蒸出溶剂，剩余物经硅胶层析提纯，用氯仿-甲醇(15：2)洗脱。得16.4g化合物(Ⅱ)，收率76.7%，在220℃软化，229-231℃熔化。
化合物(Ⅱ)(10.0g，26mmo1)和28ml二硫化碳在75rnJ二甲亚砜中，在28ml5mol/L氢氧化钠水溶液存在下反应，然后用73ml 3-溴丙腈进行烷化。粗品经硅胶层析提纯，氯仿-甲醇(20：1)洗脱。得10.2g化合物(Ⅲ)，收率61%，熔点 150-155℃(分解)(氯仿-乙醚)。
化合物(Ⅲ)(5.0g，7.8mmo1)溶于甲苯中，在回流下滴加三正丁基氢化锡(17.3g，59mmo1)和1.5g偶氮二异丁腈在干燥甲苯中的溶液，约1h滴完。反应结束后，减压蒸出溶剂，剩余物经硅胶柱炔速层析提纯，氯仿-甲醇(20：1)洗脱。得2.3g化合物(Ⅳ)，收率28%，熔点178-180℃(甲醇-丙酮)。
化合物(Ⅳ)(3.0g，8.6mmo1)和lmol/L四正丁基氟化铵在34ml四氢呋喃中，进行脱保护基反应。蒸出溶剂，剩余物经硅胶柱层析提纯，氯仿-甲醇(7：1)洗脱。得1.36g化合物(V)，收率67%，熔点＞310℃(甲醇)。
化合物(V)(0.38g，1.6mmo1)溶于70ml乙醇-水(4：1)的混合液中，在0.07g 10%钯-炭存在下，于0.35MPa的氢压下氢化6h。过滤，滤液浓缩，冷却。滤集固体，干燥，得0.3g去羟肌苷，收率78%。

方法2：在搅拌下，将2.15kg肌苷加到5.27kg 2-乙酰氧基-2-甲基丙酰氯和7.2kg碘化钠在40L乙腈的溶液中，搅拌30min。将反应液倾入饱和碳酸氢钠水溶液中，用乙酸乙酯提取。提取液用亚硫酸氢钠水溶液和饱和氯化钠水溶液洗，浓缩。剩余物溶于48L吡啶-丙酮(1：2)的混合液中，加入锌-铜复合物(由6.0kg锌粉和2%硫酸铜反应得到)，彻底搅拌。然后移出未反应的锌-铜复合物，先用Amberlite IRC 718，再用10%氨/甲醇处理．得到55%的化合物(Ⅵ)。将其溶于2%氨水中，在Raney镍存在下氢化，得到38.5%的去羟肌苷。

方法3：2'-脱氧肌苷(Ⅶ)先5'-O-苯甲酰化，再3’-0-(1-咪唑基)硫代羰基化，然后脱去3’-氧，再去苯甲酰基，得到去羟肌苷。

方法4：6-羟基嘌呤(hywzanthine)和2’，3’-二脱氧胞啶(2’，3’-dideoxycy-tidine)、2’，3'-脱氧尿核苷(2’，3'-dideoxyuridine)或3’-脱氧胸腺嘧啶核苷(3’-de-oxythymidine)，在Escherichia(如Escherichia co1i JA-300)、Klebsiella或Erwinia存在下，在磷酸缓冲水溶液中，进行发酵，可以得到去羟肌苷。

地丹诺辛海关

[ 海关编码 ]: 2942000000

地丹诺辛文献

Absence of a universal mechanism of mitochondrial toxicity by nucleoside analogs.

Antimicrob. Agents Chemother. 51 , 2531-9, (2007)

Nucleoside analogs are associated with various mitochondrial toxicities, and it is becoming increasingly difficult to accommodate these differences solely in the context of DNA polymerase gamma inhibi...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

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