1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione
Doxifluridine
CAS: 3094-09-5
Molecular Formula: C9H11FN2O5
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Names and Identifiers
| Name | Doxifluridine |
| Synonyms | 5'-DFUR Doxifluridine 5μdFUrd, Doxifluridine 5-Fluoro-5'-deoxyuridine 5'-deoxy-5-fluoro-uridin 5'-Deoxy-5-fluorouridine (2xi)-5'-deoxy-5-fluorouridine 5μdFUrd, 5-Fluoro-5μ-deoxyuridine Capecitabine Related Compound B (20 mg) (5'-deoxy-5-fluorouridine) 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-oxolan-2-yl]-5-fluoro-pyrimidine-2,4-dione 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl]-5-fluoro-pyrimidine-2,4-quinone |
| CAS | 3094-09-5 |
| EINECS | 221-440-1 |
| InChI | InChI=1/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6?,8?/m1/s1 |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Physico-chemical Properties
| Molecular Formula | C9H11FN2O5 |
| Molar Mass | 246.19 |
| Density | 1.3751 (estimate) |
| Melting Point | 188-192°C(lit.) |
| Specific Rotation(α) | D25 +18.4° (c = 0.419 in water) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | White solid |
| Color | White |
| Merck | 14,3437 |
| pKa | 7.4(at 25℃) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Refractive Index | 20 ° (C=1, H2O) |
| MDL | MFCD00866530 |
| Physical and Chemical Properties |
|
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | YU7526000 |
| HS Code | 29349990 |
| Hazard Note | Irritant |
| Hazard Class | IRRITANT, IRRITANT-H |
| Toxicity | LD50 (14 day) in mice or rats (mg/kg): >1000 i.v.: >2000 s.c.; in male, female mice, male, female rats (mg/kg): >5000, >5000, 3471, 3390 orally (Shimizu) |
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Nature
Open Data Verified Data
from methanol ethyl acetate acicular crystals, melting point of 192~193 deg C; From ethyl acetate crystallization, melting point of 189~190 deg C; From 2 propanol crystallization, melting point of 186~188 deg C.
Last Update：2024-01-02 23:10:35
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Preparation Method
Open Data Verified Data
5-fluorouracil nucleoside and p-toluenesulfonic acid monohydrate are suspended in acetone and 2,2-= methoxypropane, stirred at room temperature until clear, and excess sodium bicarbonate solid is added, stirring was continued to neutrality. Filtration, washing of the filter cake with acetone, evaporation of the wash and filtrate to dryness, and recrystallization of the resulting material from ethyl acetate gave the ketalate of 5-fluorouracil nucleoside. This was dissolved in dimethylformamide, triphenylphosphonium methyl iodide compound was added, left at room temperature, methanol was added, and the solvent was distilled off. The remaining oil was shaken with ethyl acetate and an aqueous solution of sodium thiosulfate and allowed to stand to separate. The separated ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness. The obtained oil was recrystallized from ethyl acetate to obtain a fluorourinary derivative. The obtained fluorourinary derivative was dissolved in methanol and triethylamine, and was reduced by hydrogenation under the action of a palladium-carbon catalyst at normal pressure, room temperature and vigorous stirring. The catalyst was removed by filtration and washed with methanol. The washing liquid and filter residue were evaporated to dryness, and then stirred with ethyl acetate. The treated material was reacted with aqueous trifluoroacetic acid, the reaction solution was evaporated to dryness, and ethanol was added, water and trifluoroacetic acid were removed azeotropically and evaporated to dryness. The resulting material was recrystallized from ethyl acetate to obtain doxifluridine.
Last Update：2022-01-01 09:09:03
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Standard
Authoritative Data Verified Data
This product is a 5 '-deoxy-5-fluorouracil nucleoside. The content of C9H11FN205 shall be between 98.0% and 102.0% based on the dry product.
Last Update：2024-01-02 23:10:35
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Trait
Authoritative Data Verified Data
- This product is white or off-white needle-like crystal or crystalline powder.
- This product is dissolved in water, slightly soluble in methanol, slightly soluble in ethanol, almost insoluble in ether.
melting point
The melting point of this product (General rule 0612) is 188~193°C, melting and decomposition.
specific rotation
take this product, precision weighing, add water to dissolve and quantitatively dilute to make a solution containing about 10mg per lml, and determine according to law (General rule 0621), the specific rotation was 18.0 ° to 21.0 °.
Last Update：2022-01-01 11:34:06
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Use
Open Data Verified Data
Roche Pharmaceutical Co., Ltd., Japan, was first launched in September 1987. Developed by Roche, Switzerland, Hoffmann-La. Fluorouracil antitumor drugs, as the prodrug of fluorouracil. Thymidine phosphorylase exists in the tumor tissue, and acts to transform it into Fluorouracil in the tumor, thereby playing an anti-tumor role. Its anti-tumor specificity is strong and its toxicity is low. Clinically used for gastric cancer, colon cancer, rectal cancer, breast cancer, etc.
Last Update：2022-01-01 09:09:03
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Differential diagnosis
Authoritative Data Verified Data
- take about 0.2g of this product, Add 10ml of water to dissolve, add 1 ml of bromine test solution, shake, and the red color will disappear.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 716).
- This product shows the identification reaction of organic fluoride (General rule 0301).
Last Update：2022-01-01 11:34:06
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Safety
Open Data Verified Data
mice or rats (14 days) LD50(mg/kg):>l000 I. V.,>2000 S.C. Male and female mice, male and female rats oral LD50(mg/kg):>5000,>5000,>3471,>3390.
Last Update：2022-01-01 09:09:04
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Exam
Authoritative Data Verified Data
acidity
take 0.20g of this product, add 20ml of water to dissolve, and then measure it according to law (General rule 0631). The pH value should be 4.0~5.5.
free fluoride ion
take 1.0g of this product, precision weighing, put it in a 100ml measuring flask, and add sodium chloride-sodium citrate buffer (take 55g of sodium chloride and 0.5g of sodium citrate, put it in a 1000ml measuring flask, add about 350ml water to dissolve, carefully add human sodium hydroxide 75g, shake to dissolve, let cool, carefully add human glacial acetic acid 225ml while stirring, let cool, add isopropanol 300ml, dilute to 1000ml with water, shake well. The pH value of the buffer is 5.0~5.5) dissolve and dilute to the scale, shake well, as a test solution; Another precision weighing 105 mg of sodium fluoride after drying at 22.1°C for 4 hours, add 20ml of water to dissolve in a 100ml measuring flask, Add 10ml of 0.04% sodium hydroxide solution, dilute with water to the scale, shake well, and take appropriate amount, solutions containing lug, 3UG, 5ug and 10ug of sodium fluoride per 1 ml were prepared by diluting with the above sodium chloride-sodium citrate buffer solution, respectively, as serial control solutions. Potentiometric Titration Method (General 0701), the use of fluoride ion electrode-calomel electrode were measured series of reference solution and test solution potential. Free fluoride (F-) should not exceed 0.05%.
Related substances
take an appropriate amount of this product, add the mobile phase to dissolve and dilute to make a solution containing about 1 mg per 1ml as a test solution; Take 1ml for precision measurement and put it in a 200ml measuring flask, dilute to the scale with the mobile phase, shake, and serve as a control solution. For the chromatographic conditions under the content determination item, 20ul of the test solution and the control solution are accurately measured and injected into the human liquid chromatograph respectively, and the chromatogram is recorded to 7 times of the retention time of the main 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 the area of the main peak of the control solution (0.5% ) , the sum of each impurity peak area shall not be greater than 2 times (1.0%) of the main peak area of the control solution.
loss on drying
take this product, dry to constant weight at 105 ° 0, and lose no more than 0.5% of weight (General rule 0831).
ignition residue
take l.Og of this product, put it in a platinum crucible, and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
chloride
take 0.14g of this product, according to the chloride inspection method (General 0801), the chloride content shall not exceed 0.035%.
Last Update：2022-01-01 11:34:07
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with eighteen alkyl silane was used as filler 1, and water-acetonitrile-methanol (75:5:20) was used as mobile phase; The detection wavelength was 269nm. The number of theoretical plates is not less than 1500 calculated as the peak of doxifluridine.
assay
take the right amount of this product, precision weighing, plus mobile phase dissolution and quantitative dilution made in each lml containing about 0.lmg solution, shake, as a test solution, take 20ul precision, injection of human liquid chromatography, record chromatogram; Another precision call to take the appropriate amount of doxifluridine reference, the same method for determination, according to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 11:34:08
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Category
Authoritative Data Verified Data
antineoplastic agents.
Last Update：2022-01-01 11:34:08
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:34:08
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Doxifluridine tablets
Authoritative Data Verified Data
This product contains doxifluridine (C9H11FN2O5) should be 93.0% to 107.0% of the label.
trait
This product is white or off-white.
identification
- take an appropriate amount of the fine powder of this product (equivalent to 0.2g of deoxy-fluridine), add 10ml of water, shake to dissolve deoxy-fluridine, filter, take the filtrate and shake with 1 ml of bromine test solution, the red color disappeared.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- take an appropriate amount of fine powder of this product and add 0.1 mol/L hydrochloric acid solution is dissolved and diluted to prepare a solution containing about 10ug of deoxyfluridine in each LML, filtered, and the continued filtrate is taken as the test solution, as determined by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at a wavelength of nm and a minimum absorption at a wavelength of Nm.
examination
- for related substances, take the stock solution of the test product under the content determination item as the test solution; Take 1ml for precision measurement, put it in a 200ml measuring flask, and dilute it to the scale with mobile phase, as a control solution. According to the method for the determination of the related substances of the oxygen. If there are Miscellaneous peaks in the chromatogram of the test solution, the peak volume of a single impurity shall not be greater than the area of the main peak of the control solution (0.5% ) , the sum of each impurity peak area shall not be greater than 3 times (1.5%) of the main peak area of the control solution.
- dissolution dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), hydrochloric acid solution (9-1000) 900ml as the dissolution medium, the rotation speed is 50 rpm, operate in accordance with the law, after 30 minutes, take the solution to filter, take the appropriate amount of the filtrate, dilute with the dissolution medium to make a solution containing about 10 mesh of deoxyfluridine per 1 ml, measure absorbance at the wavelength of 269nm by UV-Vis spectrophotometry (General rule 0401), the dissolution medium was added to dissolve and quantitatively dilute to prepare a solution containing about 10ug per 1 ml, and the dissolution amount of each tablet was calculated by the same method. The limit is 80% 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 10 tablets of this product, precision weighing, fine grinding, precision weighing fine powder appropriate amount (equivalent to 25mg of doxyfluridine), put 25ml measuring flask, add appropriate amount of water, ultrasonic treatment for about 10 minutes to dissolve doxifluridine, take out, cool, dilute to the scale with mobile phase, shake, filter, take the continued filtrate as the sample stock solution; take 10ml accurately, put it in a 100ml measuring flask, dilute it to the scale with mobile phase, shake it, and use it as a test solution, and measure it according to the method under the item of doxifluridine.
category
with doxifluridine.
specification
0.2g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:34:09
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Doxifluridine Dispersible Tablets
Authoritative Data Verified Data
This product contains deoxyfluridine (C9H11FN205) should be 93.0% to 107.0% of the label.
trait
This product is white or off-white.
identification
- take an appropriate amount of fine powder of this product (about 0.2g equivalent to doxifluridine), add 10ml of water, shake, filter, take the filtrate and 1 ml of bromine test solution, shake, the red color will disappear.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- take an appropriate amount of fine powder of this product, add water to dissolve and dilute to make a solution containing about loxouridine l0ug per lm l, filter and take the filtrate as UV-Vis spectrophotometry (General 0401) it was determined that there was a maximum absorption at a wavelength of 269nm and a minimum absorption at a wavelength of 234nm.
examination
- relevant substances: take an appropriate amount of the fine powder of this product, add the mobile phase to dissolve and dilute to prepare a solution containing about 1 mg of deoxyfluridine per 1ml, filter it, and take the continued filtrate as the test solution; take 1ml of precision, 200ml flask, diluted with mobile phase to the scale, shake, as a control solution. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution and the control solution are accurately measured, and the human liquid chromatograph is injected respectively, and the chromatogram is recorded to 7 times of the retention time of the main 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 the area of the main peak of the control solution (0.5% ), the sum of each impurity peak area shall not be greater than 3 times (1.5%) of the main peak area of the control solution.
- dissolution dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), hydrochloric acid solution (9-100) as the dissolution medium, the speed is rpm, operate in accordance with the law, after 15 minutes, take the solution to filter, take the appropriate amount of the filtrate, dilute with the dissolution medium to make a solution containing 10ug of doxyfluridine per 1 ml, measure absorbance at the wavelength of 269nm by UV-Vis spectrophotometry (General rule 0401), the dissolution medium is added to dissolve and quantitatively dilute to prepare a solution containing about 10ug per lml, which is determined by the same method, and the dissolution limit of each tablet is calculated to be 80% of the labeled amount, which shall be in accordance with the regulations.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Water-acetonitrile-methanol (75:5:20) as mobile phase; The detection wavelength was 269nm. The number of theoretical plates is not less than 1500 calculated as the peak of doxifluridine.
- determination of 10 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 25mg equivalent to doxifluridine), put in a 25ml measuring flask, add an appropriate amount of water, ultrasonic treatment for about 10 minutes to dissolve doxifluridine, take it out, cool it, dilute it to the scale with mobile phase, shake it well, filter it, take 10ml of the continuous filtrate and put it in a 100ml measuring flask, dilute to the scale with mobile phase, shake well, as a test solution, take 20u1 injection of human liquid chromatograph with precision, record chromatogram; Take appropriate amount of desoxyfluridine reference with precision, add the mobile phase to dissolve and dilute to make each 1 ml containing 0.lmg solution, the same method for determination. According to the external standard method to calculate the peak area, that is.
category
with doxifluridine.
specification
0.2g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:34:10
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione - Doxifluridine Capsules
Authoritative Data Verified Data
This product contains deoxyfluridine (C9H11FN205) should be 93.0% to 107.0% of the label.
trait
The content of this product is white or white particles or powder.
identification
- take an appropriate amount of the contents of this product (equivalent to 0.2g of deoxyfluridine), add 10ml of water, shake to dissolve deoxyfluridine, filter, take the filtrate and add 1 ml of bromine test solution, shake, the red color disappeared.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- take an appropriate amount of the contents of this product and add 0.1 mol/L hydrochloric acid solution is dissolved and diluted to prepare a solution containing about 10ug of deoxyfluridine in each LML, filtered, and the continued filtrate is taken as the test solution, as determined by UV-Vis spectrophotometry (General rule 0401), there is a maximum absorption at a wavelength of nm and a minimum absorption at a wavelength of Nm.
examination
- for related substances, take the stock solution of the test product under the content determination item as the test solution; Take 1ml of the sample for precise measurement, put it in a 200ml measuring flask, dilute it to the mark with the mobile phase, and mix well, as a control solution. According to the method for the determination of the related substances of the oxygen. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.5% ), the sum of each impurity peak area shall not be greater than 3 times (1.5%) of the main peak area of the control solution.
- dissolution the dissolution of this product was determined according to the dissolution and release determination method (General rule 0931, Method 1), with hydrochloric acid solution (9-100) as the dissolution medium, and the rotation speed was rpm, operate in accordance with the law, after 30 minutes, take the solution to filter, take the appropriate amount of the filtrate, dilute with the dissolution medium to make a solution containing 10ug of doxyfluridine per 1 ml, measure the absorbance at the wavelength of 269mn according to UV-Vis spectrophotometry (General rule 0401); Take appropriate amount of doxifluridine reference by precision weighing, the dissolution medium is added to dissolve and quantitatively dilute to prepare a solution containing about 10ug per 1 ml, which is determined by the same method, and the dissolution amount of each particle is calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
take the contents under the difference of loading amount, mix evenly, weigh an appropriate amount (about 25mg equivalent to doxyfluridine), put it in a 25ml measuring flask, and add an appropriate amount of water, ultrasonic treatment for about 10 minutes to dissolve doxifluridine, cool, dilute to the scale with mobile phase, shake, filter, take the continued filtrate as a stock solution for the test sample; Take 10ml with precision, in a 100ml measuring flask, dilute to the scale with the mobile phase, shake well, as a test solution, according to the method under the item of doxifluridine, then get.
category
with doxifluridine.
specification
0.2g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:34:11
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Product Name: 5′-dFUrd Visit Supplier Webpage Request for quotationCAS: 3094-09-5
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Spot supply
Product Name: Capecitabine Impurity 16(Capecitabine EP Impurity B) Visit Supplier Webpage Request for quotationCAS: 3094-09-5
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: 5′-dFUrd Visit Supplier Webpage Request for quotationCAS: 3094-09-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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