Adenosine 腺苷

CAS 58-61-7 MFCD00005752

化学结构图

58-61-7
SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

化学属性

Mol. FormulaC10H13N5O4
Mol. Weight267.24
Melting Point234-236°C
Density2.08
TSCAYes
Boiling Point676.3°C at 760 mmHg

别名和识别编码

Chemical NameAdenosine
Synonym Adenosine {LY} Adenosine {} {LY} Adenosine {} {} {LY} Adenosine {} {} {} {LY} Adenosine {} {} {} {} {LY} Adenosine {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenosine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00005752
Beilstein Registry Number93029
CAS Number58-61-7
EC Number200-389-9
PubChem Substance ID87561839
Merck Number153
Chemical Name Translation腺苷
Reaxys-RN93029
Wiswesser Line NotationT56 BN DN FN HNJ IZ D- BT5OTJ CQ DQ E1Q
LabNetwork Molecule IDLN00194348
InChIInChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
Canonical SMILESNC1=C(N=CN2[C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C2=NC=N1
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分类

  • {SNA} A-AM, Allium cepa (Onion), Allium sativum (Garlic), Bioactive Small Molecule Alphabetical Index, Other Biochemical, Panax ginseng, Phytochemicals by Chemical Classification, Phytochemicals by Plant (Food/Spice/Herb), 生物活性小分子, 细胞生物学, 营养研究
  • Analytical Standards, Analytical/Chromatography, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards
  • {SNA} A-AM, Adenosines/P2 Nucleotide Receptor - Agonists, Adenosines/P2 Nucleotide Re
  • {SNA} A-AM, Adenosines/P2 Nucleotide Receptor - Agonists, Adenosines/P2 Nucleotide Receptors (Purinergics), Agonists, Allium cepa (Onion), Allium sativum (Garlic),

产品应用

  • 内源性的神经递质。
  • 医药工业上主要用于制造阿糖腺苷(Ara-AR);腺苷三磷酸(ATP);辅酶A(COASH)及其系列产品环磷酸腺苷(CAMP)等药物的主要原料。

相关文献及参考

  • [2]. Borea PA, Gessi S, Merighi S, Vincenzi F, Varani K. Pharmacology of Adenosine Receptors: The State of the Art. Physiol Rev. 2018;98(3):1591-1625.
  • [3]. Eltzschig HK. Adenosine: an old drug newly discovered. Anesthesiology. 2009;111(4):904-915.
  • [4]. Zhou XT, et al. Inhibition of autophagy enhances adenosine induced apoptosis in human hepatoblastoma HepG2 cells. Oncol Rep. 2019;41(2):829-838.
  • Merck:14,153
  • Merck:14,153 Beilstein:31,27
  • [1]. Fredholm BB. Adenosine, an endogenous distress signal, modulates tissue damage and repair. Cell Death Differ. 2007;14(7):1315-1323.
  • [1]. Fredholm BB. Adenosine, an endogenous distress signal, modulates tissue damage and repair. Cell Death Differ. 2007;14(7):1315-1323.
  • [2]. Borea PA, Gessi S, Merighi S, Vincenzi F, Varani K. Pharmacology of Adenosine Receptors: The State of the Art. Physiol Rev. 2018;98(3):1591-1625.
  • [3]. Eltzschig HK. Adenosine: an old drug newly discovered.

安全信息

WGK Germany2
Signal word Warning
GHS Symbol
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSAU7175000
Hazard Codes Xn
Storage condition 2-8°C {LY} 2-8°C 2-8℃保存 {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {}
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 240 ug/kg
TOXIC EFFECTS :
   Cardiac - arrhythmias (including changes in conduction)
REFERENCE :
   AJEMEN American Journal of Emergency Medicine.  (WB Saunders, Philadelphia,
   PA)  V.1-    1983-  Volume(issue)/page/year: 14,300,1996

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 171 ug/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Behavioral - coma
   Cardiac - pulse rate
REFERENCE :
   AJEMEN American Journal of Emergency Medicine.  (WB Saunders, Philadelphia,
   PA)  V.1-    1983-  Volume(issue)/page/year: 11,192,1993

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD277-689

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - man
DOS

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 360 ug/kg/1H-I
TOXIC EFFECTS :
   Cardiac - pulse rate increase, without fall in BP
   Cardiac - change in rate
REFERENCE :
   AJEMEN American Journal of Emergency Medicine.  (WB Saunders, Philadelphia,
   PA)  V.1-    1983-  Volume(issue)/page/year: 10,326,1992

T

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 100 umol/L
REFERENCE :
   JIDEAE Journal of Investigative Dermatology.  (Williams & Wilkins Co., 428
   E. Preston St., Baltimore, MD 21202)  V.1-    1938- Volume(issue)/page/year:
   65,52,1975

TYPE OF TEST            : DNA damage
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 60 mmol/L
REFERENCE :
   PNASA6 Proceedings of the National Academy of Sciences of the United States
   of America.  (National Academy of Sciences, Printing & Pub. Office, 2101
   Constitution Ave., Washington, DC 20418) V.1-    1915-
   Volume(issue)/page/year: 48,686,1962

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 1 gm/L
REFERENCE :
   ZAPOAK Zeitschrift fuer Allgemeine Mikrobiologie.  (Akademie-Verlag GmbH,
   Postfach 1233, Berlin DDR-1086 Ger. Dem. Rep.)  V.1-    1960-
   Volume(issue)/page/year: 12,583,1972

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 178 mg/kg
REFERENCE :
   NULSAK Nucleus (Calcutta).  (Dr. A.K. Sharma, Centre of Advanced Studies in
   Cell and Chromosome Research, Calcutta, 35 Baliygunge Circular Rd., Calcutta
   700 019, India)  V.1-    1958-  Volume(issue)/page/year: 17,199,1974

其他信息

  • 阿糖腺苷:阿糖腺苷是一种人工合成的抗肿瘤化合物,为腺苷类衍生物,可从放线菌发酵液中提取,具有广谱的抗疱疹病毒和嗜肝DNA病毒的作用,进入感染细胞后生成有生物活性的三磷酸阿糖腺苷。干扰病毒DNA的合成,为广谱抗病毒药。静脉给药迅速进入细胞内,肾、肝、脾的浓度很高,脑脊液的浓度为血中的1/3。本品对疱疹病毒、腺病毒、水痘病毒、乙肝病毒等有显著抑制作用,但对RNA病毒无效。较之同类产品的碘苷、阿糖腺苷对DNA病毒的深部感染或复发性感染更有效,比阿糖胸苷毒性低、作用弱。 阿糖腺苷在组织培养内有广谱抗DNA病毒作用,可抑制单纯疱疹病毒Ⅰ、Ⅱ型,水痘——带状疱疹病毒、巨细胞病毒、E-B病毒、痘病毒和假狂犬病毒。三磷酸阿糖腺苷能抑制单纯疱疹和乙型肝炎病毒DNA多聚酶。对碘苷和其他类型抗疱疹药无交叉耐药性。动物试验对家兔疱疹病毒角膜炎和小鼠疱疹病毒和痘病毒脑炎有效,但对豚鼠皮肤疱疹病毒感染效果差,对黑猩猩、人乙型肝炎病毒感染有效。阿糖腺苷毒性小,大剂量有致畸胎、致突变作用。阿糖腺苷的作用机理尚
  • 用途三:抗心律失常药,可使阵发性室上性心动过速转为窦性心律。用于和房室有关的室上心律失常。
  • {
  • 稍微可溶于水,实际上不溶于醇。
  • 毒性分级:中毒
  • 下游产品:阿糖腺苷 --> 5'-核糖核苷酸钙
  • Alfa Aesar:腺苷,99% Adenosine, 99%(58-61-7)
  • 所属类别二:生物化学品: 核酸类: 核苷及其衍生物
  • 阿糖腺苷:阿糖腺苷是一种人工合成的抗肿瘤化合物,为腺苷类衍生物,可从放线菌发酵液中提取,具有广谱的抗疱疹病毒和嗜肝DNA病毒的作用,进入感染细胞后生成有生物活性的三磷酸阿糖腺苷。干扰病毒DNA的合成,为广谱抗病毒药。静脉给药迅速进
  • 生理功能:腺苷是以核苷和嘌呤为基本构造的活性物质,是由腺嘌呤通过β-糖苷键结合D-核糖形成的一种核苷,它广泛地存在于所有类型的细胞中,在核酸中既可是游离的也可是化合的核苷。像ATP这样的腺苷磷酸酯是生物化学反应中重要的能量载体。 腺苷为一天然核苷酸,是机体代谢的中间产物,也是体内重要活性成分之一。其作用系通过激活腺苷受体(A受体)而实现。在心房、窦房结及房室结,腺苷通过与A受体结合而激活G蛋白偶联的钾通道,使K+外流增加,细胞膜超极化而降低自律性。它还能明显增加cGMP水平,延长房室结的ERP和减慢传导,抑制交感神经或异丙肾上腺素所致早后、迟后除极而发挥抗心律失常作用。本品暂未被分类于Ⅰ~Ⅳ类抗心律失常药中。 腺苷是中枢神经系统的一种抑制性神经调质,可在大脑的能量储存及能量需求之间提供信号,使之达到一种平衡。在正常情况下,细胞外腺苷浓度维持在40~400nmoL。当缺血缺氧时,葡萄糖和糖原均加速分解产生ATP以应能量需求,ATP继而降解,使细胞内腺苷水平急剧升高,并释放到细胞
  • 腺苷价格(试剂级):更新日期 产品编号 产品名称 包
  • 生理功能:腺苷是以核苷和嘌呤为基本构造的活性物质,是由腺嘌呤通过β-糖苷键结合D-核糖形成的一种核苷,它广泛地存在于所有类型的细胞中,在核酸中既可是游离的也可是化合的核苷。像ATP这样的腺苷磷酸酯是生物化学反应中重要的能量载体。 腺苷为一天然核苷酸,是机体代谢的中间产物,也是体内重要活性成分之一。其作用系通过激活腺苷受体(A受体)而实现。在心房、窦房结及房室结,腺苷通过与A受体结合而激活G蛋白偶联的钾通道,使K+外流增加,细胞膜超极化而降低自律性。它还能明显增加cGMP水平,延长房室结的ERP和减慢传导,抑制交感神经或异丙肾上腺素所致早后、迟后除极而发挥抗心律失常作用。本品暂未被分类于Ⅰ~Ⅳ类抗心律失常药中。 腺苷是中枢神经系统的一种抑制性神经调质,可在大脑的能量储存及能量需求之间提供信号,使之达到一种平衡。在正常情况下,细胞外腺苷浓度维持在40~400nmoL。当缺血缺氧时,葡萄糖和糖原均加
  • 腺苷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 65000531 腺苷;腺素苷;胰苷;腺呤配糖;腺尿环核苷 1g 49.8元 2011/08/23 K0189001 腺苷(2-8℃) 5g 410元 2011/04/16 A0152 腺苷 Ade
  • F:10-23
  • {C
  • MOL 文件:58-61-7.mol

系列性分类


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