4-Hydroxypyrazolo[3,4-d]pyrimidine
4-Hydroxypyrazolo[3,4-d]pyrimidine
CAS: 315-30-0
Molecular Formula: C5H4N4O
4-Hydroxypyrazolo[3,4-d]pyrimidine - Names and Identifiers
| Name | 4-Hydroxypyrazolo[3,4-d]pyrimidine |
| Synonyms | ACO ALO Adenock NSC 101655 Allopurinol ALLOPURINOL(P) ALLOPURINOL,USP AllopurinolBp2001 Hydroxypyrazolodpyrimidine pyrazolo(3,4-d)pyrimidin-1-ol 4-Oxopyrazolo[3,4-d]pyrimidine 1H-Pyrazolo[3,4-d]pyrimidin-4-ol 4-Hydroxypyrazolo[3,4-d]pyrimidine 4-Hydroxypyrazolo(3,4-d)-pyrimidine 4-hydroxy-1H-pyrazolo(3,4-d)pyrimidine 1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one 1,5-DIHYDRO-4H-PYRAZOLO[3,4-D]PYRIMIDIN-4-ONE(ALLOPURINOL) |
| CAS | 315-30-0 |
| EINECS | 206-250-9 |
| InChI | InChI=1/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10) |
| InChIKey | OFCNXPDARWKPPY-UHFFFAOYSA-N |
4-Hydroxypyrazolo[3,4-d]pyrimidine - Physico-chemical Properties
| Molecular Formula | C5H4N4O |
| Molar Mass | 136.11 |
| Density | 1.4295 (rough estimate) |
| Melting Point | >300 °C (lit.) |
| Boling Point | 250.36°C (rough estimate) |
| Flash Point | 209.787°C |
| Water Solubility | 0.35 g/L (25 ºC) |
| Solubility | Very slightly dissolved in water or ethanol. Insoluble in chloroform or ether; soluble in sodium hydroxide or potassium hydroxide. |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White to off-white solid |
| Color | White or almost white |
| Merck | 14,279 |
| pKa | 10.2(at 25℃) |
| Storage Condition | 15-25°C |
| Sensitive | Sensitive to light |
| Refractive Index | 1.8500 (estimate) |
| MDL | MFCD00599413 |
| Physical and Chemical Properties | Melting point 350°C water-soluble 0.35g/L (25°C) |
| Use | Anti-gout drugs for the treatment of gout, gouty nephropathy, etc |
4-Hydroxypyrazolo[3,4-d]pyrimidine - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R43 - May cause sensitization by skin contact R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24 - Avoid contact with skin. S36 - Wear suitable protective clothing. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 2 |
| RTECS | UR0785000 |
| TSCA | Yes |
| HS Code | 29335990 |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 oral in mouse: 78mg/kg |
4-Hydroxypyrazolo[3,4-d]pyrimidine - Upstream Downstream Industry
| Raw Materials | Cyanoacetamide hydrazine hydrate |
4-Hydroxypyrazolo[3,4-d]pyrimidine - Reference
| Reference Show more | 1. Deng Baoqin, Zhou Jiangrong. Study on decolorization process of total saponins from saponines by reduction method [J]. Journal of Jiangxi Normal University (Natural Science Edition), 2019, 43(01):94-99. 2. Li Jing, Liu Wen, Chen Chao, Yu Jinbao. Content difference of main chemical components in three different parts of psyllium and comparison of inhibitory effect of xanthine oxidase in vitro [J]. Practical clinical practice of integrated traditional Chinese and Western medicine, 2018,18(07):174-176. 3. Zhang Ya, Wang Yiqiao, Ma Zhuoya, et al. Optimization of water extraction and alcohol precipitation process of zhuangyao Baijin granules by pharmacodynamic experiment combined with orthogonal test [J]. China Pharmacy, 2020, v.31;No.674(08):28-34. 4. Xing Zhihua, Bao Ran, Jiang dianwen, etc. Synthesis of apigenin-samarium complex and its anti-hyperuricemia effect in mice. Research and development of natural products. 5. Zhong Yingying, Zhou Jiamin, Ye Meifeng, He Xianghui, Xing Hanhan, Ye Yun. Inhibition of xanthine oxidase activity by extracts from leaves of Moringa oleifera [J]. Food industry, 2020,41(11):55-58. 6. Liu, Yongjie, et al. "Inhibition and molecular mechanism of diosmetin against xanthoxase by multiple Spectra and molecular docking. New Journal of Chemistry 44.17 (2020): 6799-6809.https://doi.org/10.1039/D0NJ00679C 7. [IF=7.132] Li Yang et al."Supercritical extraction and antioxidant activity of major ingredients in Puerariae lobatae root, Pinus massoniana needle, Citrus reticulata peel and their mixture."J Co2 Util. 2021 Jun;48:101518 8. [IF=4.411] Xiaoke Wang et al."Novel Carbon Dots Derived from Puerariae lobatae Radix and Their Anti-Gout Effects."Molecules. 2019 Jan;24(22):4152 9. [IF=4.219] Huilong Xiang et al."Network pharmacology and molecular docking analysis on molecular targets: Mechanisms of baicalin and baicalein against hyperuricemic nephropathy."Toxicol Appl Pharm. 2021 Aug;424:115594 10. [IF=3.981] Wenhao Xu et al."Self-assembled nanocapsules of celery (Apium graveolens Linn) seed oil: Mechanochemical preparation, characterization and urate-lowering activity."J Drug Deliv Sci Tec. 2021 Dec;66:102810 11. [IF=3.591] Yongjie Liu et al."Inhibition and molecular mechanism of diosmetin against xanthine oxidase by multiple spectroscopies and molecular docking."New J Chem. 2020 May;44(17):6799-6809 12. [IF=3.24] Yinfang Gao et al."Uricase-deficient rats with similarly stable serum uric acid to human's are sensitive model animals for studying hyperuricemia."Plos One. 2022 Mar;17(3):e0264696 13. [IF=3.373] Yiyuan Luo et al."Quality evaluation of Tetrastigma hemsleyanum different parts based on quantitative analysis of 42 bioactive constituents combined with multivariate statistical analysis."PHYTOCHEMICAL ANALYSIS. 2022 Apr 05 14. [IF=4.24] Jun Li et al."In vitro xanthine oxidase inhibitory properties of Flos Sophorae Immaturus and potential mechanisms."Food Biosci. 2022 Jun;47:101711 |
4-Hydroxypyrazolo[3,4-d]pyrimidine - Nature
Open Data Verified Data
- This product is white or off-white crystalline powder; Almost odorless. Very slightly soluble in water or ethanol, insoluble in chloroform or ether; Soluble in sodium hydroxide or potassium hydroxide.
- It is an isomer of hypoxanthine in vivo, inhibits xanthine oxidase, and blocks the pathway for synthesizing uric acid from hypoxanthine and xanthine, thereby lowering the concentration of uric acid in blood. Allopurinol itself can also be catalyzed by xanthine oxidase to produce xanthine, which also has the effect of inhibiting xanthine oxidase.
Last Update：2024-01-02 23:10:35
4-Hydroxypyrazolo[3,4-d]pyrimidine - Standard
Authoritative Data Verified Data
This product is 1H-pyrazolo [3,4-d] pyrimidin-4-ol. The content of C5H4N40 shall be between 97.0% and 102.0% based on the dry product.
Last Update：2024-01-02 23:10:35
4-Hydroxypyrazolo[3,4-d]pyrimidine - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Almost odorless.
- This product is very slightly soluble in water or ethanol, insoluble in trioxymethane or ether; Soluble in 0.1 mol/L sodium hydroxide or potassium hydroxide solution.
Last Update：2022-01-01 11:57:31
4-Hydroxypyrazolo[3,4-d]pyrimidine - Introduction
Allopurinol is an anti-urolithic Xanthine oxidase inhibitor that decreases uric acid production.
Last Update：2022-10-16 17:24:32
4-Hydroxypyrazolo[3,4-d]pyrimidine - Use
Open Data Verified Data
- anti-gout drug.
- usage and dosage of oral, daily 0.2~0.4g, once or divided; Also used for leukemia, lymphoma.
Last Update：2022-01-01 11:12:24
4-Hydroxypyrazolo[3,4-d]pyrimidine - Differential diagnosis
Authoritative Data Verified Data
- take about 50mg of this product, add 5ml of 5% sodium hydroxide solution, and add 1ml of alkaline potassium iodide test solution, heat to boiling, and then place it to form yellow precipitate.
- take the solution under the content determination item, according to UV-visible spectrophotometry (General rule 0401), there is a maximum absorption at the wavelength of 250nm, there is minimal absorption at a wavelength of 231nm. The absorbance ratio at 231nm to 250mn wavelength should be between 0.52 and 0.60.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 194).
Last Update：2022-01-01 11:57:31
4-Hydroxypyrazolo[3,4-d]pyrimidine - Safety
Open Data Verified Data
- should be used with caution in pregnant women; Some patients may have skin rash, gastrointestinal reactions and liver and hematopoietic system damage, such as elevated transaminase and leukopenia; When combined with anticancer drug 6-mercaptopurine, the 6-mercaptopurine dose was reduced to a constant of 1/4. Drink more water to facilitate the excretion of uric acid.
- under shading, sealed and preserved.
Last Update：2022-01-01 11:12:24
4-Hydroxypyrazolo[3,4-d]pyrimidine - Exam
Authoritative Data Verified Data
- Related substances take about 15mg of this product, put it in a 25ml measuring flask, add 12.5ml of 0.4% sodium hydroxide solution to dissolve, dilute it to the mark with hydrochloric acid solution (9-1000), and shake it well, as a test solution; 1ml was accurately measured, placed in a 100ml measuring flask, diluted to the scale with mobile phase, and shaken to serve as a control solution. According to the high performance liquid chromatography (General rule 0512) test, silica gel bonded with eighteen alkyl silane was used as the filler; Methanol-0.125% potassium dihydrogen phosphate solution (20:80) was used as the mobile phase; The detection wavelength was 230nm; the number of theoretical plates shall not be less than 2000 calculated by allopurinol peak, and the separation degree between allopurinol peak and adjacent impurity peaks shall meet the requirements. 20ul of control solution and 20ul of test solution were respectively injected into human liquid chromatograph, and the chromatogram was recorded to 2.5 times of the retention time of principal component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than 0.5 times (0.5%) the area of the main peak of the control solution, and the sum of the areas of each impurity peak shall not be greater than the area of the main peak of the control solution (1.0%).
- weight loss on drying this product shall be dried at 105°C to constant weight, and the weight loss shall not exceed 0.5% (General rule 0831).
Last Update：2022-01-01 11:57:32
4-Hydroxypyrazolo[3,4-d]pyrimidine - Content determination
Authoritative Data Verified Data
take about 20mg of this product, precision weighing, Add 10ml of 0.4% sodium hydroxide solution to dissolve, dilute quantitatively with hydrochloric acid solution (9-1000) to make a solution containing about 10ug per 1 ml, the absorbance was measured at a wavelength of 0401 NM according to ultraviolet-visible spectrophotometry (General rule 571), and the absorption coefficient of C5H4N40 was calculated.
Last Update：2022-01-01 11:57:33
4-Hydroxypyrazolo[3,4-d]pyrimidine - Category
Authoritative Data Verified Data
anti-gout drugs.
Last Update：2022-01-01 11:57:33
4-Hydroxypyrazolo[3,4-d]pyrimidine - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:57:33
4-Hydroxypyrazolo[3,4-d]pyrimidine - Allopurinol tablets
Authoritative Data Verified Data
This product contains allopurinol (C5H4N40) should be labeled the amount of 93.0% to 107.0%.
trait
This product is white tablet.
identification
- take an appropriate amount of fine powder of this product (about 0.1g of allopurinol), add 10ml of 5% sodium hydroxide solution, stir to dissolve allopurinol, filter, and take 5ml of filtrate, the same response was shown in the identification (1) Test under allopurinol.
- the solution under the content measurement item was taken, and the same result was shown according to the test of identification item (2) under the allopurinol item.
- take an appropriate amount of fine powder (about 50mg of allopurinol), add 10ml of sodium hydroxide solution, grind to dissolve, filter, acidify the filtrate with dilute hydrochloric acid to precipitate crystals, filter, the crystals were washed with absolute ethanol, washed with anhydrous ether, dried at room temperature, dried at 105 ° C. For 3 hours, and measured according to the law. The infrared absorption spectrum of this product should be consistent with the spectrum of the control (Spectrum set 194 Figure).
examination
- Related substances take an appropriate amount of fine powder of this product (equivalent to 15mg of allopurinol), put it in a 25ml measuring flask, add 0. 4% sodium hydroxide solution 12.5ml to dissolve the fermentation broth, dilute to the scale with hydrochloric acid solution (9-1000), shake well, filter, and take the continued filtrate as the test solution; Take 1 ml with precision, set in a 100ml measuring flask, dilute to the scale with the mobile phase, and shake to serve as a control solution. The determination was carried out according to the method for related substances of allopurinol. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than 0.5 times (0.5%) the area of the main peak of the control solution, and the sum of the areas of each impurity peak shall not be greater than the area of the main peak of the control solution (1.0%).
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 second method), with hydrochloric acid solution (9-1000) 1000ml as the dissolution medium, the rotation speed is 100 rpm, operate according to law, after 45 minutes, take 10ml of the solution, filter, take 5ml of the filtrate with precision, put it in a 50ml measuring flask, dilute it to the scale with dissolution medium, and shake well. The absorbance was measured at a wavelength of 0401 NM according to ultraviolet-visible spectrophotometry (General rule 571), and the elution amount of each tablet was calculated as the absorption coefficient of C5H4N4O was. The limit is 70% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 20 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (about equivalent to allopurinol 0.lg ), put it in a 100ml measuring flask, add 0.2% sodium hydroxide solution 20ml, shake for 15 minutes to dissolve allopurinol, dilute to the scale with water, shake well, filter, accurately take 5ml of continued filtrate, put it in a 500ml measuring flask, dilute to the scale with hydrochloric acid solution (9-1000), shake well. The absorbance was measured at a wavelength of 0401 NM according to ultraviolet-visible spectrophotometry (General rule 571), and the absorption coefficient of C5H4N40 was calculated.
category
Same as allopurinol.
specification
O.lg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:57:34
4-Hydroxypyrazolo[3,4-d]pyrimidine - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | allopurinol is a white or white-like crystalline powder, almost odorless. allopurinol is mainly used in the interictal and chronic phases of gout. it is suitable for patients with primary and secondary gout who produce too much uric acid, are allergic or ineffective to uric acid excretion drugs, and are not suitable for using uric acid excretion drugs to control hyperuricemia. it can also be used in combination with uric acid excretion drugs, in order to strengthen the curative effect, it is especially suitable for patients with severe tophi and good renal function. |
| usage and dosage | 1. adults: the initial dose is 50mg once, 1-2 times a day, increasing 50-100mg per week to 200-300mg per day, divided into 2-3 times. Blood and uric acid levels are measured every 2 weeks. If they have reached normal levels, they will no longer increase. If they are still high, they will increase again. However, the maximum amount per day shall not be greater than 600mg. 2. Children: 50mg each time within 6 years old, 1~3 times a day; 6~10 years old, 100mg once, 1~3 times a day. The dosage can be adjusted as appropriate. |
| indications | 1. primary and secondary hyperuricemia, especially hyperuricemia caused by excessive uric acid production. 2. recurrent or chronic gout; 3. uric acid kidney stones and/or uric acid nephropathy; 4. hyperuricemia with renal insufficiency. |
| Pharmacological action and mechanism of action | Allopurinol and its metabolite oxopurinol inhibit the activity of xanthine oxidase (the latter can convert hypoxanthine into xanthine, and then xanthine into uric acid), so that uric acid production is reduced, and the uric acid content in blood and urine is reduced to a level below solubility, thereby preventing the deposition of uric acid stones, contribute to the re-dissolution of gout nodules and uric acid crystals. |
| pharmacokinetics | it is easy to absorb by oral administration and can absorb 80% ~ 90% from gastrointestinal tract. About 70% of the dosage is metabolized into active oxypurinol in the liver, which is excreted by the kidney, and about 10% is excreted in the urine with prototypes and 70% metabolites. |
| preparation | 1) triethyl orthoformate, morpholine, acetonitrile and cyanoacetamide are sequentially put into the reaction vessel for stirring, steam is heated to reflux, reflux reaction is 4h, the initial reflux temperature will be 117 ℃, and the final reflux temperature will be 82 ℃. the mixture obtained after reflux is cooled to 25-35 ℃, then wash and vacuum dry in sequence to obtain the condensate; 2) Put the purified water, the condensate obtained in step 1), and hydrazine hydrate into the reaction vessel in order for stirring, and quickly heat to 90-100°C, and Keep the temperature above 90°C for 20 minutes, then cool the mixture to 60°C, then add dilute sulfuric acid and ice for hydrolysis and acidification reaction; acidification reaction to 5°C and then collect crystalline hydrates, finally, the crystalline hydrate is washed and vacuum dried to obtain the semi-sulfate of 3-amino -4-pyrazole formamide; 3) The semi-sulfate of 3-amino -4-pyrazole formamide is added to the formamide, stirred and heated to 140-150 ℃, heat preservation reaction for 5 hours, after the reaction, the reactants are cooled to 25-35 ℃, and the allopurinol crude is obtained by washing; 4) allopurinol crude and activated carbon are added to concentrated hydrochloric acid for decolorization. The decolorized product is added to 25 ℃ sodium hydroxide solution for recrystallization. Finally, allopurinol products are obtained by washing and vacuum drying. |
| use | allopurinol and its metabolite xanthine all have the effect of inhibiting lixanthine oxidase, thus blocking uric acid synthesis, reducing the concentration of uric acid in blood and reducing the deposition of uric acid in bones, joints and kidneys. It is clinically used for gout and gouty nephropathy. Pregnant women should use it with caution; some patients may have rash, gastrointestinal reactions, and liver and hematopoietic system damage, such as elevated transaminases and leukopenia; when combined with anticancer drug 6-mercaptopurine, the dose of 6-mercaptopurine should be reduced to constant 1/4. Drink more water to facilitate uric acid excretion. Anti-gout drugs. It is suitable for various diseases with primary or secondary serum uric acid increase, such as gout, acute or chronic leukemia, etc. inhibitors of xanthine oxidase (xanthine oxidase) and pyridine synthesis. |
| production method | ethyl cyanoacetate, triethyl orthoformate and acetic anhydride are placed in a reaction tank for reflux reaction for 4 hours to obtain ethyl α-ethoxymethycyanoacetate. then it is dissolved in ethanol, hydrazine hydrate is added, and the reflux reaction is heated for 6 hours to obtain 3-amino -4-ethoxycarbonyl pyrazole. Finally, it is heated and refluxed with formamide for 8 hours, cyclization yields allopurinol. Dissolve with distilled water and decolorize with activated carbon to obtain refined allopurinol. For ethyl cyanoacetate, the total yield 41.8% |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD > 500 mg/kg; Oral-mouse LD50: 78 mg/kg |
| flammability hazard characteristics | combustible, the fire field discharges nitrogen-containing oxides and pungent smoke |
| storage and transportation characteristics | warehouse is low temperature, ventilated and dry; Store separately from food raw materials |
| fire extinguishing agent | water, carbon dioxide, dry powder, foam |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:08
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Raw Materials for 4-Hydroxypyrazolo[3,4-d]pyrimidine