Dideoxycytidine 4-氨基-1-((2R,5S)-5-(羟甲基)四氢呋喃-2-基)嘧啶-2(1H)-酮

CAS 7481-89-2 MFCD00012188

化学结构图

7481-89-2
SMILES: Nc1ccn([C@H]2CC[C@@H](CO)O2)c(=O)n1

化学属性

Mol. FormulaC9H13N3O3
Mol. Weight211.22
Density1.422
Melting Point217-218°C
TSCANo
Solubility5-10 G/100 ML AT 19 ºC
Refractive index78 ° (C=0.5, H2O)

别名和识别编码

Chemical NameDideoxycytidine
CAS Number7481-89-2
Synonym Zalcitabine {LY} Zalcitabine ddC ddC (Antiviral) dideoxycytidine {} {LY} Zalcitabine {} {} {LY} Zalcitabine {} {} {} {LY} Zalcitabine {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Zalcitabine {} {} {} {} {} {} {} {
EC Number250-023-7
Beilstein Registry Number654956
MDL NumberMFCD00012188
PubChem Substance ID24066
Merck Number10109
Chemical Name Translation4-氨基-1-((2R,5S)-5-(羟甲基)四氢呋喃-2-基)嘧啶-2(1H)-酮
Reaxys-RN654956
LabNetwork Molecule IDLN01314316
InChIInChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1
Canonical SMILESOC[C@@H]1CC[C@H](N2C=CC(N)=NC2=O)O1
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分类

  • {Chemicalbo
  • {SNA} Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology,
  • {SNA} Bioactive Small Molecules, Biochemicals and Reagents, D-DIF, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides, 细胞生物学
  • Nucleotides
  • {SNA} AIDS and Viral Research Reagents, Bioactive Small Molecules, Biochemicals and Reagents, Cell Signaling and Neuros

产品应用

  • A pyrimidine nucleoside analogue with antiviral activity.

相关文献及参考

  • van der Vliet, P.C. and Kwant, M.M.: Biochemistry, 20, 2628 (1981),
  • Mitsuya, H., Broder, S.: Proc. Nat. Acad. Sci. USA, 83, 1911 (1986),
  • Starnes, M.C., and Cheng, Y.: J. Biol. Chem., 262, 988 (1987),

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • 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
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
Precautionary statements
  • 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。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P263 Avoid contact during pregnancy/while nursing. 怀孕/哺乳期间避免接触。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • 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。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P305+P351+P338
  • P308+P313
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H351 Suspected of causing cancer 怀疑致癌
  • 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
RTECSHA3870000
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Hazard Codes Xn
Storage condition 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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 91 mg/kg/13W-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Endocrine - tumors
REFERENCE :
   FAATDF Fundamental and Applied Toxicology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1981-  Volume(issue)/page/year:
   27,263,1995

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 200 nmol/L
REFERENCE :
   MOPMA3 Molecular Pharmacology.  (Williams & Wilkins Co., 428 E. Preston St.,
   Baltimore, MD 21202) V.1-    1965-  Volume(issue)/page/year: 39,625,1991

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 600 mg/kg/3D (Continuous)
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

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 20 gm/kg
SEX/DURATION            : female 6-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 42,131,1990

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 10 gm/kg
SEX/DURATION            : female 6-15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 42,131,1990

其他信息

  • TCI Shanghai:2',3'-二脱氧胞苷 2',3'-Dideoxycytidine,>;98.0%(LC)(T)(7481-89-2)
  • 用途二:作用于HIV复制的早期,抑制病毒的逆录酶和终止病毒DNA链的复制。用于晚期免疫缺陷病毒感染患者的治疗。
  • Alfa Aesar:2',3'-二脱氧胞啶,98+% 2',3'-Dideoxycytidine, 98+%(7481-89-2)
  • 上游原料:氨 --> 钯 --> 氢 --> 乙酰溴 --> 胞苷
  • 图谱信息:扎西他滨(7481-89-2)红外图谱(IR1) 扎西他滨(7481-89-2)质谱(MS)
  • 用途一:抗病毒药,用于抗癌、抗艾滋病毒
  • F:10-23
  • 方法一:N-乙酰基胞嘧啶核苷(4g,14mmo1)在200ml乙腈中回流,在30min内滴加乙酰溴(10ml,0.137mo1),加毕再回流3h。蒸出溶剂,剩余物溶于100ml氯仿后,用100ml水洗。蒸去氯仿,剩余物用10ml乙醇重结晶,得2g无色片状结晶的化合物(I),收率33%,熔点179-180℃(分解)。 化合物(I)(1g,2.3mmo1)、lg碳酸钙、0.2g钯-硫酸钡和50ml 50%甲醇,在25℃和常压下与氢气摇晃1h(吸收60ml氢)。过滤除去结晶,滤液浓缩至干。剩余物溶于10ml 20%氨-甲醇溶液,于5℃下放置过夜。柱层析后再用乙醇重结晶,得34mg无色结晶的扎西他滨,收率7%。
  • 扎西他滨价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D3581 2',3'-二脱氧胞苷 2',3'-Dideoxycytidine 1G 1390元 2010/05/25 L10619 2',3'-二脱氧胞啶, 98+% 2',3'-Dideoxycytidine, 98+% 50mg 749元 2010/05/25 L10619 2',3'-二脱氧胞啶, 98+% 2',3'-Dideoxycytidine, 98+% 250mg 2674元
  • MSDS 信息:DDC(7481-89-2).msds
  • Sigma Aldrich:7481-89-2(sigmaaldrich)
  • MOL 文件:7481-89-2.mol

系列性分类


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