CAS 24356-66-9 MFCD00065471-(2R,3S,4S,5R)-2-(6-Amino-9H-Purin-9-Yl)-5-(Hydroxymethyl)Tetrahydrofuran-3,4-Diol Hydrate (2R,3S,4S,5R)-2-(6-氨基-9H-嘌呤-9-基)-5-(羟甲基)四氢呋喃-3,4-二醇水合物 TAO{mole}

(2R,3S,4S,5R)-2-(6-Amino-9H-Purin-9-Yl)-5-(Hydroxymethyl)Tetrahydrofuran-3,4-Diol Hydrate (2R,3S,4S,5R)-2-(6-氨基-9H-嘌呤-9-基)-5-(羟甲基)四氢呋喃-3,4-二醇水合物

CAS 24356-66-9 MFCD00065471

化学结构图

SMILES: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |&1:10,12,15,17|

化学属性

Mol. Formula	C10H13N5O4·H2O
Mol. Weight	267.25(as Anhydrous)
Melting Point	260
Appearance	本品为白色针状结晶或结晶性粉末。无臭；无味；微溶于水(0.45 mg/ml)、甲醇，几乎不溶于乙醚。mp259-261℃。本品单磷酸酯的溶解度为100 mg/ml。

别名和识别编码

Chemical Name	(2R,3S,4S,5R)-2-(6-Amino-9H-Purin-9-Yl)-5-(Hydroxymethyl)Tetrahydrofuran-3,4-Diol Hydrate
MDL Number	MFCD00065471
Reaxys-RN	93029
CAS Number	24356-66-9
Merck Number	9976
Beilstein Registry Number	26(3/4)3598
PubChem Substance ID	87560128
Synonym	ci673 腺嘌呤阿拉伯糖苷,ADENINE ARABINOSIDE VIDARABINE 9-beta-D-阿拉伯呋喃糖基腺嘌呤 9-beta-d-arabinofuranosyl-9h-purin-6-amin 9-Β-D-阿拉伯呋喃糖基腺嘌呤 arasena-a beta-ara-a 6-AMINO-9-BETA-D-ARABINOFURANOSYLPURINE 9-arabinosyladenine 9-BETA-D-ARABINOFURANOSYLADENINE 阿糖腺嘌呤 ci-673 SPONGOADENOSINE 9-beta-D-Arabinofuranosyladenine monohydrate 9-β-D-Arabinofuranosyladenine Ara-A Vidarabine 阿糖腺苷 9-Β-D-阿拉伯呋喃糖腺嘌呤,9-Β-D-ARABINOFURANOSYLADENINE MONOHYDRATE 9H-Purin-6-amine, 9-beta-D-arabinofuranosyl-, monohydrate 2'-ARAADENOSINE adeninearabinoside ADENINE-9-BETA-D-ARABINOFURANOSIDE ARABINOSYL-ADENINE Adenine 9-β-D-arabinofuranoside beta-d-arabinosyladenine 9-beta-D-Arabinofuranosyl-9H-purine-6-amine monohydrate araadenosine ARA-A 9-beta-d-arabinofuranosyl-adenin 9-BETA-D-ARABINOSYLADENINE ADENINE-BETA-D-ARABINOFURANOSIDE
EC Number	226-893-9
Chemical Name Translation	(2R,3S,4S,5R)-2-(6-氨基-9H-嘌呤-9-基)-5-(羟甲基)四氢呋喃-3,4-二醇水合物
Wiswesser Line Notation	T56 BN DN FN HNJ IZ D- ET5OTJ B1Q CQ DQ &QH*D-ARABINO

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分类

{SNA} A-AM, Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antiviral, Bioactive Small Molecules, Biochemicals and Reagents, Chemical Structure Class, Inhibits an Enzyme, Interferes with DNA Synthesis, Mechanism of Action, Nucleosides, Preservatives and Disinfectants, Spectrum of Activity, 细胞生物学
{Chemicalbook} 生物化学品: 核酸类: 核苷及其衍生物
{SNA} A-AM, Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antiviral, Bioactive Small Molecules, Cell Biology, Chemical Structure Class,
{SNA} Antib

安全信息

RTECSAU6200000

Signal word Warning

Precautionary statements

P501 Dispose of contents/container to..… 处理内容物/容器.....
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。
P308+P313
P281 Use personal protective equipment as required. 使用所需的个人防护装备。
P405 Store locked up. 上锁保管。
P201 Obtain special instructions before use. 使用前获取专门指示。
P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。

Hazard statements

H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害

WGK Germany3

GHS Symbol

Hazard Codes Xn

Safety Statements

S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；

Risk Statements

R63 Possible risk of harm to the unborn child 可能危害未出生婴儿

Packing GroupII

Storage condition -20°C 储存温度-20°C

Hazard Class6.1(a)

UN Number 2811

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4677 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Gastrointestinal - peritonitis
REFERENCE :
   AACHAX Antimicrobial Agents and Chemotherapy (1961-70).  (Ann Arbor, MI)
   1961-70.  For publisher information, see AMACCQ.  Volume(issue)/page/year:
   -,180,1968

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >7950 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AACHAX Antimicrobial Agents and Chemotherapy (1961-70).  (Ann Arbor, MI)
   1961-70.  For publisher information, see AMACCQ.  Volume(issue)/page/year:
   -,180,1968

其他信息

急性毒性:腹腔-大鼠 LD50: 1476 毫克/公斤; 口服-小鼠 LD50: 3057 毫克/公斤
可燃性危险特性:可燃; 燃烧产生有毒氮氧化物烟雾
储运特性:库房通风低温干燥
MOL 文件:5536-17-4.mol
毒性分级:中毒
上游原料:N,N-二甲基甲酰胺 --> 三氯氧磷 --> 4-甲苯磺酰氯 --> 氢硫酸 --> 磷酸酯 --> 脱硫 --> 5'-腺嘌呤核苷酸 --> 尿嘧啶 --> 磷酸化酶 --> 腺苷 --> 嘌呤核苷磷酸化酶 --> 尿苷 --> 阿糖尿苷
Sigma Aldrich:5536-17-4(sigmaaldrich)
用途一:有抗单纯疱疹病毒HSV-1和HSV-2作用，用于治疗单纯疱疹病毒性脑膜炎，也用于免疫抑制病人的带状疱疹和水痘感染。但对巨细胞病毒无效。本品的单磷酸酯有抑制乙肝病毒复制的作用。当剂量在每日10mg/kg以上时，可出现厌食、恶心、呕吐、腹泻、转氨酶升高、头晕、乏力等。少数还可出现骨髓抑制，主要表现为白细胞和血小板减少。本药有致畸作用，孕妇禁用。乳母、婴儿及肝、肾功能不全者慎用。
方法一:方法一、以5'-腺嘌呤核苷酸(5'-AMP)为原料经选择性对甲苯磺酰化，水解脱磷，溴化，乙酰化得8-羟基-N，3', 5'-O-三乙基-2’-O-对甲苯磺酰基腺苷，在甲醇-氨中环化，再在甲醇-硫化氢中开环得8-巯基阿糖腺苷，经氢解脱硫即可得阿糖腺苷。 5'-腺嘌呤核苷酸[对甲苯磺酰氯]→2'-O-对甲苯磺酰基腺苷-5’-单磷酸酯[氨水，甲酰胺]→2’-O-对甲苯磺酰基腺苷酸[Br 2 ]→8-溴-2’-O-对甲苯磺酰基腺苷[乙酸，醋酐]→8-羟基-N, 3', 5'-O-三乙基-2'-O-对甲苯磺酰基腺苷[甲醇氨]→8, 2'-O-环化腺苷[甲醇-硫化氢]→8-巯基阿糖腺苷[兰尼镍]→阿糖腺苷方法二、以尿苷为原料先与三氯氧化磷和二甲基甲酰胺反应，然后在碱性(pH=9)条件下水解得到阿糖尿苷，经嘧啶核苷磷酸化酶水解，温度60℃，脱去尿嘧啶得到阿糖-1-磷酸，经嘌呤核苷磷酸化酶催化，与腺嘌呤在60℃缩合得阿糖腺苷。尿苷[三氯氧化磷，二甲基甲酰胺]→[pH9]阿糖尿苷[嘧啶核苷磷酸化酶]→[60℃]阿糖-1-磷酸[嘌呤核苷磷酸化酶]→[60℃]阿糖腺苷。
F:10-23
刺激数据:皮肤-兔子 3% 轻度; 眼睛-兔子 1% 中度
MSDS 信息:9-beta-D-Arabinosyladenine(5536-17-4).msds
灭火剂:干粉,泡沫,沙土,二氧化碳, 雾状水
类别:有毒物品