1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
Stavudine
CAS: 3056-17-5
Molecular Formula: C10H12N2O4
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Names and Identifiers
| Name | Stavudine |
| Synonyms | ZERIT Stavir STAVUDINE Stavudine NSC 163661 3'-deoxythymidin-2'-ene 3'-DEOXY-2',3'-DIDEHYDROTHYMIDINE 3'-deoxy-2',3'-didehydrothymidine 2',3'-didehydro-3'-deoxythymidine Thymidine, 2'', 3''-didehydro-3''-deoxy- STAVUDINE[2'',3''-DIDEHYDRO-3''-DEOXYTHYMIDINE] 1-[5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-hexahydropyrimidine-2,4-dione 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione |
| CAS | 3056-17-5 |
| EINECS | 641-374-0 |
| InChI | InChI=1/C10H14N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-3,6-8,13H,4-5H2,1H3,(H,11,14,15) |
| InChIKey | XNKLLVCARDGLGL-JGVFFNPUSA-N |
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Physico-chemical Properties
| Molecular Formula | C10H12N2O4 |
| Molar Mass | 224.21 |
| Density | 1.374±0.06 g/cm3(Predicted) |
| Melting Point | 159-160°C |
| Specific Rotation(α) | D25 -39.4° (c = 0.701 in water); D20 -46.1° (c = 0.7 in water) |
| Water Solubility | 5-10 g/100 mL at 21 ºC |
| Solubility | Soluble in DMSO, methanol, water (83 mg/ml) at 23 °C, chloroform, ethanol, and propylen |
| Appearance | neat |
| Color | White |
| pKa | 9.47±0.10(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | -46 ° (C=0.69, H2O) |
| MDL | MFCD00132921 |
| Physical and Chemical Properties | Melting point 159-160°C water-soluble 5-10g/100 mL at 21°C |
| Use | Used as an antiviral drug |
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-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. |
| WGK Germany | 2 |
| RTECS | XP2075000 |
| HS Code | 29349990 |
| Toxicity | LD50 oral in rat: 4gm/kg |
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Nature
Open Data Verified Data
A colorless granular solid was obtained from ethanol-benzene and had a melting point of 165-166 °c. Crystals from ethanol ether, melting point 174 °c, have also been reported. UV absorption maximum (water):266nm(e10149).[a]210-46.1.(c = 0.7, water), [a]Do - 39.4 has also been reported. (c = 701. Water).
Last Update：2024-01-02 23:10:35
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Preparation Method
Open Data Verified Data
thymidine was dissolved in anhydrous pyridine, and methanesulfonyl chloride was added dropwise under ice salt cooling, stirred, filtered, and dried under vacuum to obtain a sulfonylated crude product. The crude product was recrystallized from 90% ethanol to obtain excellent product. The sulfonylated product was dissolved in an aqueous solution of sodium hydroxide and refluxed. After neutralization with hydrochloric acid, the solvent was distilled off, chloroform was added to the residue, insoluble matter was filtered off, chloroform was distilled off, and the mixture was crystallized from acetic acid and ethanol to obtain an epoxy compound as a white solid. Recrystallization with ethanol for 2 Times gave a white flocculent solid. This epoxy was dissolved in dimethyl sulfoxide, potassium tert-butoxide was added, and the mixture was stirred at room temperature. Neutralized to pH = 7 with 50% acetic acid in ethanol. It was concentrated under reduced pressure and the resulting material was washed with hot acetone. The washing liquid was filtered and concentrated, and then ethanol was added. The activated carbon was decolorized and filtered. Ethanol was distilled off, and a small amount of benzene was added for rotary evaporation until the solution became turbid and allowed to stand. The precipitated solid was recrystallized from ethanol-benzene (1:5) to give Stavudine as a white powder.
Last Update：2022-01-01 09:08:11
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Standard
Authoritative Data Verified Data
This product is 1-(2, 3-dideoxy-B-D-glyceryl-pentyl-2-enofuranosyl) thymine. The content of C10H12N2O4 should be between 98.0% and 102.0% based on the anhydrous content.
Last Update：2024-01-02 23:10:35
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder.
- This product is dissolved in water, slightly soluble in ethanol or acetonitrile, and almost insoluble in n-hexane.
specific rotation
take this product, precision weighing, add water to dissolve and quantitatively dilute to prepare a solution containing 10 mg per lml, and determine according to law (General rule 0621), the specific rotation was -39.5 ° to -45.9 °.
Last Update：2022-01-01 11:41:59
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Use
Open Data Verified Data
blesterdo Meyer, Inc. was launched in 1994. Antiviral drugs. Its high bioavailability is expected to improve the status of anti-HIV infection.
Last Update：2022-01-01 09:08:11
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Differential diagnosis
Authoritative Data Verified Data
- in the chromatogram recorded under the relevant substances, the retention time of the main peak of the test solution should be consistent with the retention time of the stavudine peak in the stavudine system applicable solution.
- 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 this product, add water to dissolve and dilute to make a solution containing about 10ug per lml, and measure by UV-Vis spectrophotometry (General 0401), there is a maximum absorption at a wavelength of 266nm and a minimum absorption at a wavelength of 235Nm.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402). If it is not consistent, the product and the reference product should be recrystallized with anhydrous ethanol for determination.
- two items (1) and (2) above can be selected as one item.
Last Update：2022-01-01 11:41:59
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Exam
Authoritative Data Verified Data
Related substances
new system for clinical use. Take the thymine reference substance, weigh it precisely, dissolve it with water and dilute it quantitatively to make a solution containing about 250ug per lml, which is used as the reference stock solution, add water to dissolve and dilute to make a solution containing about 0.5mg per lml as a test solution; Take 2ml of lml and reference stock solution, put it in the same 200ml measuring flask, and dilute it to the scale with water, as a control solution. According to the high performance liquid chromatography (General 0512) test, using eighteen alkyl silane bonded silica gel as filler, with acetonitrile -0.Olmol/L ammonium acetate solution (3.5:96.5) as mobile phase A, acetonitrile -0.Olmol/L ammonium acetate solution (25:75) was used as mobile Phase B, and the gradient elution was carried out according to the following table. The detection wavelength was 254nm. Take the appropriate amount of mixed reference substance in stavudine system suitability test, add water to dissolve and dilute to make a solution containing about 0.5mg per 1 ml as the system suitability solution [the solution contains thymine (impurity I), thymidine (impurity III) and its isomer (impurity IV), stavudine and a-stavudine (impurity II )], 10u1 injection human liquid chromatograph, the flow rate was adjusted so that the retention time of stavudine main peak was 8.5-12.5 minutes, the relative retention time of thymidine peak was about 0.28, and the relative retention time of thymidine peak was about 0.5, the degree of separation of the thymidine peak from its isomer peak should be not less than 1.15, and the degree of separation of the stavudine peak from the-stavudine peak should be not less than 1.0. The test solution and the control solution are respectively injected with human liquid chromatography, and the chromatograms are recorded. If the impurity peak is shown in the chromatogram of the test solution, thymine shall not exceed 0.5% based on the peak area calculated by external standard method, and the peak area of other individual impurities shall not be greater than 0.2 times (0.1%) of the main peak area of the control solution, the sum of the peak areas of other impurities shall not be greater than the main peak area of the control solution (0.5%).
residual solvent
methanol, isopropanol, toluene, butyl acetate, pyridine, N, N-dimethylacetamide and N-methylpyrrolidone take this product about 0.5g, precision Add Dimethyl Sulfoxide-water (1:l)10ml, shake to dissolve, as a test solution; Respectively precision weighing methanol, isopropanol, toluene, butyl acetate, pyridine, N, N-dimethylacetamide and N-methylpyrrolidone were diluted with dimethyl sulfoxide-water (1:1) to prepare methanol 0.15mg, isopropanol 0.15mg, toluene 0.0445mg, A solution of 0.15mg of butyl acetate, 0.01mg of pyridine, 0.0545mg of N, N-dimethylacetamide and 0.0265mg of N-methylpyrrolidone was stirred well and used as a reference solution. According to the residual solvent determination method (General 0861 third method), using polyethylene glycol-TPA modified capillary column, the starting temperature is 40°C, the 5 minutes, at a rate of 15°C per minute heating to 120°C, the temperature was maintained for 2 minutes and then increased to 200°C at a rate of 10°C per minute for 5 minutes; The inlet temperature was 150°C; And the detector temperature was 250°C. The sample solution and the reference solution were respectively 1u1, injected into the human gas chromatograph, and the chromatogram was recorded. The degree of separation between adjacent chromatographic peaks shall meet the requirements. The peak area shall be calculated according to the external standard method, and the content of isopropyl alcohol and butyl acetate shall not exceed 0.3%, and the others shall comply with the regulations.
chloroform
take about 0.25g of this product, precision weighing, in the top empty bottle, precision add water 5ml and anhydrous sodium sulfate lg, shake, as a test solution; Precise weighing take appropriate amount of chloroform, the solution containing 3ug per 1 ml was prepared by dissolving and quantitatively diluting with water, and 5ml was accurately measured. The solution was placed in a headspace bottle, and lg of anhydrous sodium sulfate was added and shaken to serve as a reference solution. According to the determination method of residual solvent (General Principle 0861 second method), the capillary column with 5% phenyl-95% methyl polysiloxane (or similar polarity) as the stationary liquid is the column; The column temperature is 45°C; the inlet temperature was 150°C; The detector temperature was 250°C; The headspace bottle equilibrium temperature was 90°C and the equilibrium time was 30 minutes. The test solution and the reference solution were sampled by Headspace injection, and the chromatograms were recorded. According to the external standard method to calculate the peak area, should comply with the provisions.
moisture
take 0.2g of this product, according to the determination of moisture (General 0832 first method), the water content shall not exceed 0.5%.
ignition residue
take l.Og of this product 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 burning residual Tong shall be inspected according to law (General rule 0821, second law), and the heavy metal content shall not exceed 20 parts per million.
Last Update：2022-01-01 11:42:00
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-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 the filler; Acetonitrile-O.Olmol/L ammonium acetate solution (5:95) was used as the mobile phase; The detection wavelength was 268nm. Take 5mg of thymine control, 7.5mg of thymidine control and 10mg of stavudine control, put them in the same 100ml measuring flask, add water to dissolve and dilute to the scale, shake well, take 10ml of precision, put them in 50ml measuring flask, dilute with water to the scale, shake, as the system applicable solution, take 10u1 injection liquid chromatograph, thymidine peak and thymine peak separation should be not less than 3.5, the theoretical plate number is not less than 800 calculated from the stavudine peak.
assay
precision weigh appropriate amount of this product, add water to dissolve and quantitatively dilute to make a solution containing 20ug per lml (ready to use new system), as a test solution, take 25 u1 for precision measurement, human liquid chromatograph was used and the chromatogram was recorded. Another stavudine reference substance, the same method of determination, according to the external standard method to calculate the peak area, that is obtained.
Last Update：2022-01-01 11:42:01
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Category
Authoritative Data Verified Data
antiviral drugs.
Last Update：2022-01-01 11:42:01
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:42:02
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione - Stavuding Capsule
Authoritative Data Verified Data
This product contains stavudine (C10H12N2O4) should be 90.0% to 105.0% of the label amount.
identification
- take an appropriate amount of the contents of this product (about 25TNG of stavudine), add an appropriate amount of water, shake to dissolve stavudine, dilute to 50ml with water, filter, take 1 ml of filtrate, dilute to 50ml with water, shake, according to UV-visible spectrophotometry (General rule 0401), there is a maximum absorption at 266nm wavelength, there is a minimum absorption at 235nm wavelength.
- take an appropriate amount of the content of this product (about 200mg equivalent to stavudine), add 50ml of acetone, shake vigorously, and then place it on the water bath while heating until boiling, filter it, 150ml of n-heptane was added to the filtrate, and Stavudine was fully precipitated by standing for 1 hour, filtered, the crystals were rinsed with n-heptane, the crystals were dried in air for at least 30 minutes, and the appropriate amount was taken, A solution containing 10 mg per 1 ml was prepared by dissolving and quantitatively diluting with water, and measured according to law (General rule 0621). The specific rotation was from one 39.5 ° to one 45.9 °.
- take an appropriate amount of the contents of this product (about equivalent to 20mg of stavudine), add 100ml of water, sonicate for 3 minutes, filter, and take the continued filtrate as the test solution; Take the control of stavudine, water was added to dissolve and diluted to prepare a solution containing 0.2mg per 1 ml as a control solution. According to the thin layer chromatography (General 0502) test, absorb the above two solutions of 10 u1, respectively, on the same silica gel GF254 thin layer plate, with chloroform-ethanol-water (100:25:0.5) for the development of the agent, after the deployment, dry, set the UV lamp (254nm) under the inspection. The color and position of the main spot displayed by the test solution should be the same as the main spot of the control solution.
- 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.
- two items (3) and (4) above can be selected as one item.
examination
- for related substances, take the test solution under the content determination item as the test solution (ready to use new system). Take the appropriate amount of thymine control, precision weighing, water dissolution and quantitative dilution of the solution containing about 1g per 1 ml, as a reference solution. An appropriate amount of the test solution was accurately taken and diluted with water to prepare a solution containing about 0.5ug stavudine per 1 ml as a control solution. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution, the reference solution and the control solution are respectively injected into the liquid chromatograph, the chromatogram was recorded to 2.5 times the retention time of the main peak. If the impurity peak is shown in the chromatogram of the test solution, thymine shall be calculated by the peak area according to the external standard method, and 1.0% of the indicated amount of stavudine shall not be exceeded, the Peak area of other individual impurities shall not be greater than 0.4 times (0.2%) of the main peak area of the control solution, and the total amount of impurities shall not exceed 2.0%.
- Content uniformity (15mg and 20mg specifications) take the content of 1 capsule of this product, put it in a 200ml measuring flask, add an appropriate amount of water, shake for 15 minutes to dissolve stavudine, dilute it with water to the scale, shake well, filter, take the continued filtrate as the test solution, and determine the content according to the method under the content determination item, which should comply with the regulations (General 0941).
- the dissolution of this product, according to the dissolution and release determination method (General rule 0931 second method), water 900ml as the dissolution medium, the speed of 75 rpm, according to the law, after 30 minutes, the appropriate amount of the solution was filtered, and the filtrate was taken as the test solution, water was added to dissolve and quantitatively diluted to prepare a solution containing 0.02mg per 1 ml as a control solution. Take 20 u1 of each sample solution and the reference solution, respectively, according to the chromatographic conditions under the content determination item, the detection wavelength is 254mn, and calculate the dissolution amount of each particle, 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
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-O.Olmol/L ammonium acetate solution (5:95) as mobile phase * the detection wavelength was 268mn. Take the appropriate amount of thymine control and thymidine, add water to dissolve and dilute to make a solution containing about 1 per 1 ml, as a system applicable solution. The separation degree of thymine peak and thymidine peak should be greater than 2.0. The number of theoretical plates shall not be less than 800 based on the calculation of stavudine peak, and the tailing factor shall not exceed 1.8.
- determination method: take the contents of 10 capsules of this product, precisely weigh them, mix them evenly, precisely weigh an appropriate amount (about 10mg equivalent to stavudine), put them in a 100ml measuring flask, add an appropriate amount of water, and shake them for 15 minutes, dilute to the scale with water, shake, filter, take the filtrate as a test solution (ready to use new), take 20u1 injection into human liquid chromatograph, record the chromatogram; take an appropriate amount of stavudine reference substance, precision weighing, dissolved with water and quantitative dilution to make about 0 per 1 ml. lmg solution (in the new system), the same method for the determination. According to the external standard method to calculate the peak area, that is.
category
Same as stavudine.
specification
(1) 15mg (2) 20mg (3)30mg (4) 40mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:42:03
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Product Name: Stavudine Visit Supplier Webpage Request for quotationCAS: 3056-17-5
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Spot supply
Product Name: Stavudine Visit Supplier Webpage Request for quotationCAS: 3056-17-5
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: Stavudine Visit Supplier Webpage Request for quotationCAS: 3056-17-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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