(+)-5-Iodo-2'-deoxyuridine 5-碘-2-脱氧尿苷

CAS 54-42-2 MFCD00134656

化学结构图

54-42-2
SMILES: O=c1[nH]c(=O)n([C@@H]2C[C@@H](O)[C@H](CO)O2)cc1I

化学属性

Mol. FormulaC9H11IN2O5
Mol. Weight354.10
Density2.1
Melting Point194°C
TSCAYes
Solubility1.6 G/L (20 ºC)
Stability对空气敏感,对光敏感
Appearance 本品为白色结晶性粉末。在水、甲醇、乙醇或丙酮中微溶,在氯仿或乙醚中几乎不溶;在氢氧化钠试液中易溶,在稀盐酸中微溶。mp 176-184℃ (分解)。
Refractive index30 ° (C=1, 1mol/L NaOH)

别名和识别编码

Chemical Name(+)-5-Iodo-2'-deoxyuridine
CAS Number54-42-2
Synonym Idoxuridine {LY} Idoxuridine {} {LY} Idoxuridine {} {} {LY} Idoxuridine {} {} {} {LY} Idoxuridine {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Idoxuridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00134656
EC Number200-207-8
Beilstein Registry Number30397
Merck Number4891
PubChem Substance ID87571623
Reaxys-RN30397
Chemical Name Translation5-碘-2-脱氧尿苷
Wiswesser Line NotationT6NVMVJ EI A- ET5OTJ B1Q CQ
LabNetwork Molecule IDLN00188566
Canonical SMILESO=C(N1)N([C@H]2C[C@H](O)[C@@H](CO)O2)C=C(I)C1=O
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分类

  • {SNA} Biochemicals and Reagents, Nucleosides, Nucleosides, Nucleotides, Oligonucleotides
  • Bases & Related Reagents
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP St
  • Nucleotides
  • {Chemicalbook} 生物化学品: 核酸类: 核苷及其衍生物
  • {SNA} Analytical Standards, EP Standards, EP Standards I - K, Pharmacopeia & Metrological Institutes Standards, 分析/色谱
  • {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards I - K, Pharmaceutical Standards, Pharmacopeia Standards, 分析/色谱
  • Pharmaceuticals
  • {SNA} Nucleosides, 核苷,核苷酸和寡核苷酸, 生化试剂
  • {SNA} Analytical Standards, EP Standards, EP Standards I - K, Pharmacopeia Metrological Institutes Standards, 分析/色谱
  • {SA} Biochemicals and Reagents,

产品应用

  • A cytotoxic analog of thymidine, antiviral

相关文献及参考

  • Merck:14,4891
  • Pressacco, J., et al.: Cancer Res., 54, 3772 (1994),
  • Chang, C., et al.: J. Biol. Chem., 267, 22414 (1992),
  • Merck:14,4891 Beilstein: 24,IV,1235

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
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 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • 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;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
  • S53 Avoid exposure - obtain special instructions before use 避免接触,使用前获得特别指示说明;
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
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R45 May cause cancer 可能致癌
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
  • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
  • R68 Possible risk of irreversible effects 可能有不可挽回的作用的危险
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。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • 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。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P312+P330
  • P302+P350
  • P305+P351+P338
  • P308+P313
  • P332+P313
  • P337+P313
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
RTECSYU7700000
Storage condition 2-8°C {LY} 2-8°C Air & Light Sensitive {} {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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C
Hazard statements
  • H302+H312+H332
  • 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
  • H315 Causes skin irritation 会刺激皮肤
  • H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes Xn T
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg/8W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Blood - leukemia
REFERENCE :
   EXPEAM Experientia.  (Birkhaeuser Verlag, POB 133, CH-4010 Basel,
   Switzerland)  V.1-    1945-  Volume(issue)/page/year: 29,1132,1973

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 :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,153,1995

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JJIND8 JNCI, Journal of the National Cancer Institute.  (Washington, DC)
   V.61-79, 1978-87. For publisher information, see JNCIEQ.
   Volume(issue)/page/year: 62,911,1979

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 4 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ADTEAS Advances in Teratology.  (New York, NY)  V.1-5, 1966-72.
   Discontinued.  Volume(issue)/page/year: 3,181,1968

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 15 mg/L
REFERENCE :
   CSHSAZ Cold Spring Harbor Symposia on Quantitative Biology.  (Cold Spring
   Harbor Laboratory, POB 100, Cold Spring Harbor, NY 11724)  V.1-    1933-
   Volume(issue)/page/year: 29,151,1965

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 128 mg/L
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 55802) V.1-    1959-  Volume(issue)/page/year:
   86,180,1986

{

TYPE OF TEST            : Sperm Morphology
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 100 mg/kg/5D
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: 72,4425,1975

TYPE OF TEST            : Sister chromatid exchange
TEST SYSTEM             : Human Fibroblast
DOSE/DURATION           : 50 mg/L
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   283,817,1981

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

{hazard

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Ocular
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 1350 mg/kg
SEX/DURATION            : female 6-18 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetal death
   Reproductive - Specific Developmental Abnormalities - eye/ear
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   AROPAW Archives of Ophthalmology (Chicago).  (AMA, 535 N. Dearborn St.,
   Chicago, IL 60610)  New series: V.1-44(3), 1929-50; V.64-    1960-
   Volume(issue)/page/year: 93,46,1975

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 300 mg/kg
SEX/DURATION            : female 7 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
   EXPEAM Experientia.  (Birkhaeuser Verlag, POB 133, CH-4010 Basel,
   Switzerland)  V.1-    1945-  Volume(issue)/page/year: 29,198,1973

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Ocular
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 3250 ug/kg
SEX/DURATION            : female 6-18 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetal death
   Reproductive - Specific Developmental Abnormalities - eye/ear
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   RIGAA3 Rinsho Ganka.  Clinical Ophthalmology.  (Igaku Shoin, 5-24-3 Hongo,
   Bunkyo-ku, Tokyo 113-91, Japan)  V.1-    1947-  Volume(issue)/page/year:
   26,631,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent -

其他信息

  • 上游原料:2-丙炔-1-醇 --> 2-氨基恶唑 --> 胞嘧啶 --> L-氢化乳清酸 --> 唑啉 --> 核苷
  • 比旋光度:280 ° (c=1,1M NaOH)
  • F:8-23
  • 存储注意事项:光敏感
  • MSDS 信息:2'-Deoxy-5-iodouridine(54-42-2).msds
  • 碘苷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 65010380 5-碘-2-脱氧尿核苷(+4℃) 500mg 96.8元 2011/04/16 I0258 5-碘-2'-脱氧尿苷 5-Iodo-2'-deoxyuridine 25G 6110元 2011/04/16 I0258 5-碘-2'-脱氧尿苷 5-Iodo-2'-deoxyuridine 1G 560元
  • TCI Shanghai:5-碘-2'-脱氧尿苷 5-Iodo-2'-deoxyuridine,>;99.0%(T)(54-42-2)
  • MOL 文件:54-42-2.mol
  • 检测方法:T,NMR,HPLC,Rotation
  • 敏感性:Air & Light Sensitive
  • Acros Organics:(+)-5-碘-2'-脱氧尿苷 (+)-5-Iodo-2'-deoxyuridine, 99%(54-42-2)
  • 方法一:有多种生产方法。从丙炔醇开始,经氧化、酯化,再与2-氨基噁唑啉核苷环合可得2,2-氧桥嘧啶核苷,然后经酰化、溴化、催化氢化、水解得到碘苷。从鱼精可以制取5'-脱氧胞嘧啶核苷酸,经进一步加工亦可制得碘苷。
  • Sigma Aldrich:54-42-2(sigmaaldrich)
  • 用途二:抗病毒药,用于单纯疱疹角膜炎和疱疹脑炎等。
  • 参考质量标准:原料 中国药典2000年版967页 指标名称 指标 指标名称 指标 比旋度(25℃,10mg ml) +25°-30° 5-碘尿嘧啶 分光光度法检查符合要求 干燥失重/% ≤1.0 滴眼液 中国药典2000年版967页 指标名称 指标 指标名称 指标 含量(C9H11IN2O5)/% /90.0-110.0/5-碘尿嘧啶/分光光度法检查符合要求 pH值 4.0-5.7 其他 符合滴眼剂有关规定
  • Idoxuridine is a cytotoxic, anti-viral thymidine analog.
  • 用途一:抗病毒药。用于疱疹性角膜炎及其他疱疹性眼病。长期应用可出现角膜浑浊或染色小点,不易消失。孕妇禁用。
  • 图谱信息:5-碘-2'-脱氧尿苷(54-42-2)红外图谱(IR2) 5-碘-2'-脱氧尿苷(54-42-2)红外图谱(IR1) 5-碘-2'-脱氧尿苷(54-42-2)核磁图( 1 HNMR) 5-碘-2'-脱氧尿苷(54-42-2)核磁图( 13 CNMR) 5-碘-2'-脱氧尿苷(54-42-2)质谱(MS)
  • Alfa Aesar:5-碘代-2'-脱氧尿嘧啶核苷,98% (+)-5-Iodo-2'-deoxyuridine, 98%(54-42-2)

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