1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 1,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮

CAS 315-30-0 MFCD00599413

化学结构图

315-30-0
SMILES: O=c1[nH]cnc2[nH]ncc12

化学属性

Mol. FormulaC5H4N4O
Mol. Weight136.11
Melting Point>300°C
TSCAYes
Solubility0.35 G/L (25 ºC)
Density1.89
Appearance 白色或类白色结晶性粉末;几乎无臭。在水中或乙醇中极微溶解。在氯仿或乙醚中不溶;在氢氧化钠或氢氧化钾中易溶。
Boiling Point423.2°C at 760 mmHg

别名和识别编码

Chemical Name1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
CAS Number315-30-0
Alfabeta NameALLOPURINOL
MDL NumberMFCD00599413
Synonym Allopurinol {LY} Allopurinol {} {LY} Allopurinol {} {} {LY} Allopurinol {} {} {} {LY} Allopurinol {} {} {} {} {LY} Allopurinol {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Allopurinol {} {} {} {} {} {} {} {} {} {} {} {} {} {
PubChem Substance ID135401907
EC Number206-250-9
Reaxys-RN608611
Beilstein Registry Number26(3/4)4298
Merck Number279
Chemical Name Translation1,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮
Wiswesser Line NotationT56 BMN GN INJ FQ
InChIInChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
Canonical SMILESO=C1C2=C(NN=C2)N=CN1
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分类

  • {SNA} Analytical Standards, EP Standards, EP Standards A - B, Pharmacopeia Metrological Institutes Standards, 分析/色谱
  • {SNA} Enzyme Inhibitors,
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards A - B, Pharmaceutical Standards, Pharmacopeia Standards
  • {SNA} Analytic
  • A-AM, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Enzyme Inhibitors, Enzyme Inhibitors by Type, Enzymes, Inhibitors, and Substrates, Substrate Analogs
  • {SNA} Additional Standards, Analytical Standards, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards,
  • {SNA} Enzyme Inhibitors,

产品应用

  • 黄嘌呤氧化酶(xanthine oxidase) 和吡啶合成的抑制剂。

相关文献及参考

  • [2]. Reiter S, et al. Demonstration of a combined deficiency of xanthine oxidase and aldehyde oxidase in xanthinuric patients not forming oxipurinol. Clin Chim Acta. 1990 Mar 15;187(3):221-34.
  • Gibbings, S., et al., Xanthine Oxidoreductase Promotes The Inflammatory State Of Mononuclear Phagocytes Through Effects On Chemokine Expression, Peroxisome Proliferator-activated Receptor-{gamma} Sumoylation, And HIF-1{alpha}. J. Thorac. Cardiovasc. Surg. 286 , 961-75, (2011)
  • Merck: 14,279
  • Merck: 14,279 Beilstein:26(3/4)4298
  • [1]. Pacher P, et al. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114.
  • [1]. Pacher P, et al. Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114.
  • [2]. Reiter S, et al. Demonstration of a combined deficiency of xanthine o

安全信息

Warnings IRRITANT
RTECSUR0785000
WGK Germany2
GHS Symbol
Precautionary statements
  • P301+P310
  • 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。
  • P301+P310+P330
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
  • P302+P352+P333+P313+P362+P364
  • P405 Store locked up. 上锁保管。
  • P333+P313
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
Signal word
Hazard statements
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H301 Toxic if swallowed 吞食有毒
Hazard Codes T T,Xi
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
UN Number UN 2811 6.1/PG 3
Safety Statements
  • S24 Avoid contact with skin 避免皮肤接触;
  • 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);
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后,立即用大量…(由生产厂家指定)冲洗;
  • 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
  • R25 Toxic if swallowed 吞咽有毒
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
Packing GroupIII
Hazard Class6.1
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 120 mg/kg/4W-I
TOXIC EFFECTS :
   Blood - other changes
   Skin and Appendages - dermatitis, allergic (after systemic exposure)
   Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
   CEDEDE Clinical and Experim

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 42 mg/kg/7D-I
TOXIC EFFECTS :
   Kidney, Ureter, Bladder - other changes
   Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
   AJMEAZ American Journal of Medicine.  (Technical Pub., 875 Third Ave., New
   York, NY 10022) V.1-    1946-  Volume(issue)/page/year: 76,47,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSE

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 88 mg/kg/22D-I
TOXIC EFFECTS :
   Blood - leukopenia
REFERENCE :
   ARDIAO Annals of the Rheumatic Diseases.  (British Medical Journal, Box
   560B, Kennebunkport, ME 04041)  V.1-    1939-  Volume(issue)/page/year:
   40,245,1981

TYPE OF TEST            : TDLo - Lowest published toxic dos

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 298 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YAKUD5 Gekkan Yakuji.  Pharmaceuticals Monthly.  (Yakugyo Jihosha, Inaoka
   Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan)  V.1-   1959-
   Volume(issue)/page/year: 23,715,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 100 mg/kg
SEX/DURATION            : female 10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
   JJPAAZ Japanese Journal of Pharmacology.  (Japanese Pharmacological Soc.,
   c/o Dept. of Pharmacology, Faculty of Medicine, Kyoto Univ., Sakyo-ku, Kyoto
   606, Japan)  V.1-    1951-  Volume(issue)/page/year: 22,201,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 50 mg/kg
SEX/DURATION            : female 10 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 :
   JJPAAZ Japanese Journal of Pharmacology.  (Japanese Pharmacological Soc.,
   c/o Dept. of Pharmacology, Faculty of Medicine, Kyoto Univ., Sakyo-ku, Kyoto
   606, Japan)  V.1-    1951-  Volume(issue)/page/year: 22,201,1972

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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {

其他信息

  • 用途一:抗痛风药,用于治疗痛风、痛风性肾病等
  • 别嘌醇价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 A0907 别嘌呤醇 Allopurinol 250G 3170元 2014/06/02 A0907 别嘌呤醇 Allopurinol 25G 610元 2010/06/21 121830050 别嘌醇 4-Hydroxypyrazolo[3,4-d]pyrimidine 98% 5 GR 459元
  • Sigma Aldrich:315-30-0(sigmaaldrich)
  • 类别:有毒物品
  • 用途二:别嘌呤醇及其代谢产物别黄嘌呤,均有抑制利黄嘌呤氧化酶的作用,进而使尿酸合成受阻,降低血中尿酸浓度,减少尿酸盐在骨、关节及肾脏的沉着。临床用于痛风、痛风性肾病。孕妇慎用;部分病人可出现皮疹、胃肠道反应及肝和造血系统损害,如转氨酶升高和白细胞减少;与抗癌药6-巯基嘌呤合用时,要将6-巯基嘌呤剂量减至常量的1/4。多饮水,以利尿酸排出。
  • 上游原料:水合肼 --> 氰乙酸乙酯 --> 氰乙酰胺 --> 乙氧甲叉氰乙酸乙酯 --> 3-氨基-4-乙氧羰基吡唑
  • 用途三:抗痛风药。适用于原发性或继发性血清尿酸增多的各种疾病,如痛风、急性或慢性白血病等。
  • Alfa Aesar:4-羟基吡唑并[3,4-d]嘧啶,98% 4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine, 98%(315-30-0)
  • Allopurinol is an anti-urolithic Xanthine oxidase inhibitor that decreases uric acid production.
  • MSDS 信息:1H-Pyrazolo[3,4-d]pyrimidin-4-ol(315-30-0).msds
  • MOL 文件:315-30-0.mol
  • 方法一:将氰乙酸乙酯、原甲酸三乙酯、乙酐放在反应罐中回流反应4h,缩合得到α-乙氧次甲基氰乙酸乙酯:再将其溶解在乙醇中,加入水合肼,加热回流反应6h,得3-氨基-4-乙氧羰基吡唑;最后与甲酰胺一起加热回流反应8h,环合得到别嘌醇。用蒸馏水溶解,活性炭脱色,得精制的别嘌醇。对氰乙酸乙酯计,总收率41.8%
  • 毒性分级:高毒
  • 急性毒性:口服- 大鼠 LD >; 500 毫克/ 公斤; 口服- 小鼠 LD50: 78 毫克/公斤
  • 灭火剂:水, 二氧化碳, 干粉, 泡沫
  • 可燃性危险特性:可燃, 火场排出含氮氧化物辛辣刺激烟雾
  • TCI Shanghai:别嘌呤醇 Allopurinol,>;98.0%(T)(315-30-0)
  • 图谱信息:别嘌醇(315-30-0)质谱(MS) 别嘌醇(315-30-0)红外图谱(IR2) 别嘌醇(315-30-0)红外图谱(IR1)
  • 储运特性:库房低温, 通风, 干燥; 与食品原料分开存放
  • 水中溶解度: 0.35 g/L (25°C) ,溶于稀碱和稀酸,实际上不溶于大多数有机溶剂。
  • Acros Organics:4-羟基吡唑[3,4-D]嘧啶 4-Hydroxypyrazolo[3,4-d]pyrimidine, 98%(315-30-0)
  • 用途四:黄嘌呤氧化酶(xanthine oxidase) 和吡啶合成的抑制剂。

系列性分类


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