Artenimol [inn]
alpha-Dihydroartemisinin
CAS: 81496-81-3;71939-50-9;123930-80-3
Molecular Formula: C15H24O5
Artenimol [inn] - Names and Identifiers
Artenimol [inn] - Physico-chemical Properties
| Molecular Formula | C15H24O5 |
| Molar Mass | 284.35 |
| Density | 1.24±0.1 g/cm3(Predicted) |
| Melting Point | 142-144°C |
| Boling Point | 375.6±42.0 °C(Predicted) |
| Specific Rotation(α) | +129 (c, 0.92 in CHCl3) |
| Flash Point | 181°C |
| Solubility | Easily soluble in chloroform, dissolved in acetone, slightly soluble in methanol or ethanol, almost insoluble in water. |
| Vapor Presure | 3.52E-07mmHg at 25°C |
| Appearance | White needle crystal |
| Color | White to Off-White |
| pKa | 12.61±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.542 |
| MDL | MFCD00274495 |
| Physical and Chemical Properties | White needle Crystal, odorless, bitter taste. It is soluble in chloroform and soluble in acetone. Slightly soluble in methanol or ethanol, almost insoluble in water. The melting point was 145-150 °c. |
Artenimol [inn] - Reference
| Reference Show more | 1. Zhu Chunyan, Xu Qiong, Mao Zhiyun, etc. Comparison of effects of three artemisinin derivatives on pain co-emotion disorder in mice with neuropathic pain [J]. Chinese Journal of Traditional Chinese Medicine 2018(15). 2. Li Yuanyuan, Wu Hongjuan. Electron Microscopic Study on apoptosis of human breast cancer cells induced by dihydroartemisinin in vitro [J]. Journal of Electron Microscopy 2015(02):138-141. 3. Chen, Bing, Yan, Li, Chao, Gan. Therapeutic effect of dihydroartemisinin on paraquat-induced pulmonary fibrosis in mice [J]. Journal of Guangxi Medical University 2012(02):175-178. 4. Wang, Dong Dong, et al. "Magnetically guided delivery of DHA and Fe ions for enhanced cancer therapy based on pH-responsive degradation of DHA-loaded Fe3O4 @ C @ MIL-100 (Fe) nanoparticles." Biomaterials 107 (2016): 88-101.https:// doi.org/10.1016/j.biomateria 5. Chen, Junyan, et al. "Dihydroartemisinin suppresses glioma proliferation and invasion via inhibition of the ADAM17 pathway." Neurological Sciences 36.3 (2015): 435-440.https://doi.org/10.1007/s10072-014-1963-6 6. Qu, Chengbin, et al. "Dihydroartemisinin exerts anti-tumor activity by inducing mitochondrion and endoplasmic reticulum apoptosis and autophagic cell death in human glioblastoma cells." Frontiers in cellular neuroscience 11 (2017): 310.https://doi.org/10.3 7. [IF=10.317] Dongdong Wang et al."Magnetically guided delivery of DHA and Fe ions for enhanced cancer therapy based on pH-responsive degradation of DHA-loaded Fe3O4@C@MIL-100(Fe) nanoparticles."Biomaterials. 2016 Nov;107:88 8. [IF=2.415] Chen Junyan et al."Dihydroartemisinin suppresses glioma proliferation and invasion via inhibition of the ADAM17 pathway."Neurol Sci. 2015 Mar;36(3):435-440 9. [IF=0] Ying Liu et al."Andrographolide Induces Autophagic Cell Death and Inhibits Invasion and Metastasis of Human Osteosarcoma Cells in An Autophagy-Dependent Manner."Cell Physiol Biochem. 2017;44(4):1396-1410 10. [IF=6.419] Mengyu Chen et al."Ligand-modified homologous targeted cancer cell membrane biomimetic nanostructured lipid carriers for glioma therapy."Drug Deliv. 2021;28(1):2241-2255 11. [IF=4.749] Chao Wang et al."Small-Sized MOF-Constructed Multifunctional Diagnosis and Therapy Platform for Tumor."Acs Biomater Sci Eng. 2019;5(9):4435-4441 12. [IF=2.082] Qin Guo et al."Synergistic inhibition effects of tea polyphenols as adjuvant of oxytetracycline on Vibrio parahaemolyticus and enhancement of Vibriosis resistance of Exopalaemon carinicauda."Aquac Res. 2021 Aug;52(8):3900-3910 13. [IF=5.811] |
Artenimol [inn] - Standard
Authoritative Data Verified Data
This product is (3R,5aS ,6R,8aS ,9R,10s, 12R,12aR)-octahydro -3,6, 9-trimethyl-3, 12-bridged oxy-12-pyrano [4,3-j] -1, 2-benzodithiazolin-10 (3H) alcohol. The content of C15H2405 shall be 98.0% ~ 102.0% calculated as dry product.
Last Update：2024-01-02 23:10:35
Artenimol [inn] - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder or colorless needle-like crystals; Odorless.
- This product is dissolved in acetone, slightly soluble in methanol or ethanol, and almost insoluble in water.
melting point
The melting point of this product (General rule 0612) is 145~150°C, and it is decomposed at the same time during melting.
Last Update：2022-01-01 11:33:13
Artenimol [inn] - Differential diagnosis
Authoritative Data Verified Data
- appropriate amounts of the product and the reference product of dihydroartemisinin were dissolved and diluted with toluene to prepare a solution containing about 0.1 mg per 1 ml, which was used as the test solution and the reference solution. According to the thin layer chromatography (General 0502) test, accurately absorb the above two solutions each 10 u1, point on the same silica gel G thin layer plate, with petroleum ether (boiling range is 40~60°C)-Ether (1:1) as a developing solvent, expand, dry, sprayed with 2% vanillin in sulfuric acid ethanol solution (20-100), heated at 85 ° C. For 10-20 minutes to clear spots. The position and color of the main spot displayed by the test solution should be consistent with 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.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 696).
- two items (1) and (2) above can be selected as one item.
Last Update：2022-01-01 11:33:14
Artenimol [inn] - Exam
Authoritative Data Verified Data
Related substances
new system for clinical use. Take 0.25g of this product, put it in a 25ml measuring flask, add an appropriate amount of methanol, sonicate to dissolve dihydroartemisinin, dilute it with methanol to the scale, shake it, and use it as a test solution, set in a 200ml measuring flask, dilute to the scale with methanol, and shake to serve as a control solution. According to the determination by high performance liquid chromatography (General rule 0512), using eighteen alkyl silane bonded silica gel as filler (capcellpakc18 mgii, 4.6mm X, 3um or equivalent chromatographic column with water as mobile phase A; acetonitrile was used as mobile phase B; The flow rate was 0.6ml per minute; The detection wavelength was 216nm. Gradient elution was performed as follows. Take the appropriate amount of dihydroartemisinin (two chromatographic peaks) and artemisinin reference, add the appropriate amount of methanol, ultrasonic to dissolve and dilute to prepare a mixed solution containing 1 mg of dihydroartemisinin and artemisinin per 1 ml, inject 20u1 into the liquid chromatograph, record the chromatogram, adjust the mobile phase ratio, and make the retention time of the chromatographic peak of artemisinin about 10 minutes, the retention times of a-dihydroartemisinin and B- dihydroartemisinin relative to artemisinin were about 0.6 and 0.8, and the resolution between each peak should be greater than 2.0. 20ul of the control solution and the test solution were respectively injected into the liquid chromatograph, and the chromatograms were recorded. If there are impurity peaks in the chromatogram of the test solution, they are 0.5 times (0.25%) larger than the area of the two main peaks of the control solution and not larger than the area of the two main peaks of the control solution and (0.5%). The number of impurity peaks shall not be more than 1, and the area of other single impurity peaks shall not be greater than 0.5 times (0.25%) of the area of the two main peaks of the control solution, the sum of each impurity peak area shall not be greater than 2 times (1.0%) of the sum of the two main peak areas of the control solution. Test Solution chromatogram is smaller than the control solution two main peak area and 0.1 times the chromatographic peak is ignored.
loss on drying
take this product, put the phosphorus pentoxide dryer under reduced pressure to dry to constant weight, the weight loss should not exceed 0.5% (General rule 0831).
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 taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 11:33:15
Artenimol [inn] - 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 as filler (capcellpakc18 mgii, 4.6mm X 100mm,3um or equivalent chromatographic column); Acetonitrile-water (60:40) as mobile phase; the flow rate was 0.6ml per minute; The detection wavelength was 216nm. Take appropriate amounts of dihydroartemisinin and artemisinin reference, add mobile phase to dissolve and dilute to make a mixed solution containing about 1 mg of dihydroartemisinin and artemisinin per 1 ml, inject 20ul into human liquid chromatograph, record chromatogram, dihydroartemisinin showed two chromatographic peaks, and the resolution between each component peak should be greater than 2.0.
assay
take an appropriate amount of this product, accurately weigh it, add dimethyl sulfoxide to dissolve and quantitatively dilute to make a solution containing about 4mg per lml, as a test solution, and inject it into the liquid chromatograph, record the chromatogram; Take the appropriate amount of dihydroartemisinin reference, precise weighing, the same method for determination. According to the external standard method, the peak area of dihydroartemisinin is calculated (if dihydroartemisinin has two chromatographic peaks, the sum of the two peak areas of dihydroartemisinin is calculated).
Last Update：2022-01-01 11:33:15
Artenimol [inn] - Category
Authoritative Data Verified Data
antimalarial drugs.
Last Update：2022-01-01 11:33:15
Artenimol [inn] - Storage
Authoritative Data Verified Data
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:33:16
Artenimol [inn] - Dihydroartemisinin tablets
Authoritative Data Verified Data
This product contains dihydroartemisinin (C15H2405) should be the label amount of 90.0% ~ 110.0%.
trait
This product is white tablet.
identification
- take an appropriate amount of the fine powder of this product (about 20mg of dihydroartemisinin), add 2ml of anhydrous ethanol to dissolve dihydroartemisinin, filter, add 2ml of potassium iodide test solution and 4ml of dilute sulfuric acid to the filtrate, shake well, several drops of starch indicator solution were added, and the solution showed blue-purple color.
- take an appropriate amount of fine powder of this product (about 20mg equivalent to dihydroartemisinin), add dichloromethane 10ml, shake, dissolve dihydroartemisinin, filter, evaporate the filtrate to about 2M1, as a test solution; An appropriate amount of dihydroartemisinin control was additionally taken, and dichloromethane was added to dissolve and prepare a solution containing 10 mg 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 G thin layer plate, with toluene-acetone-glacial acetic acid (90:10:2) for the development of the agent, expand, dry, spray with 2% vanillin sulfuric acid solution, the test solution of the main spot position and color should be consistent with the control solution main spot.
examination
- new system of related substances in clinical use. Take an appropriate amount of fine powder of this product (about 0.25g), put it in a 25ml measuring flask, add an appropriate amount of methanol, sonicate to dissolve dihydroartemisinin, dilute it to the scale with methanol, shake well, filter, the filtrate was taken as a test solution; 1ml was accurately measured, placed in a 200ml measuring flask, diluted to a scale with methanol, and shaken to obtain a control solution. Determination according to the method of dihydroartemisinin related substances. 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 sum of the areas of the two main peaks of the control solution (0.5% ) , the sum of each impurity peak area shall not be greater than 4 times (2.0%) of the sum of the two main peak areas of the control solution. Test Solution chromatogram is smaller than the control solution two main peak area and 0.1 times the chromatographic peak is ignored.
- dissolution the dissolution medium was 0931 sodium hydroxide-ethanol (4:l) according to the dissolution and release determination method (General rule 0.15% method), after 30 minutes, 5ml of the solution was taken, filtered, and 2ml of the filtrate was accurately taken, placed in a 10ml measuring flask, and diluted to the scale with 2% sodium hydroxide solution, as a test solution; Take an appropriate amount of dihydroartemisinin reference product, add ethanol to dissolve and quantitatively dilute to a solution containing 0.4mg per lml, place for more than 2 hours, take 2ml in precise volume, place it in a 10ml measuring flask, dilute it to the scale with 0.15% sodium hydroxide solution, place it at 37 ° C for 30 minutes, then take 2ml, place it in a 10ml measuring flask, dilute it to the scale with 2% sodium hydroxide solution, as a control solution. Place the test solution and the reference solution in a constant temperature water bath at 60°C for 30 minutes, take them out at the same time, quickly let them cool, and then perform ultraviolet-visible spectrophotometry (General rule 0401), the absorbance was measured at a wavelength of 241NM, and the elution amount of each tablet was calculated. 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 an appropriate amount (about 25mg equivalent to dihydroartemisinin), put it in a 50ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, filter, and take the continued filtrate as the test solution; Weigh about 25mg of dihydroartemisinin reference product accurately, put it in a 50ml measuring flask, add dimethyl sulfoxide to dissolve and dilute to the scale, shake well, as a control solution. Determination according to the method under the item of dihydroartemisinin content determination. According to the external standard method to calculate the peak area, that is.
category
Same as dihydroartemisinin.
specification
20mg
storage
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:33:17
Artenimol [inn] - Dihydroartemisinin and Piperaquine Phosphate Tablets
Authoritative Data Verified Data
each tablet of this product should contain dihydroartemisinin (C15H2405) 90.0% ~ 110.0% of the label amount; Containing piperaquine phosphate (C29H32C12N6 • 4H3P04) should be 93.0% ~ 107.0% of the label amount.
trait
This product is a film-coated tablet, white to light yellow after removing the coating.
identification
- take an appropriate amount of fine powder of this product (about 3.1g equivalent to piperaquine phosphate), add 10ml of water, sonicate for 10 minutes, and filter. Take 5ml of the filtrate, add 2ml of the ammonia test solution, shake well, filter, add 2ml of nitric acid to the filtrate, shake well, add 3ml of ammonium molybdate test solution, yellow precipitate, the precipitate can be dissolved in the ammonia test solution.
- take an appropriate amount of the fine powder of this product (about 10mg equivalent to dihydroartemisinin), add 80% ethanol, sonicate to dissolve dihydroartemisinin, filter, and take the filtrate as the test solution; in addition, 10mg of dihydroartemisinin control and 80mg of piperaquine phosphate control were dissolved by adding 5ml of 80% ethanol (dissolved by ultrasound if necessary), respectively, as a reference solution. According to the thin layer chromatography (General 0502) test, Draw 5 u1 of each of the above three solutions, respectively point on the same silica gel gf2m-plate, with dichloromethane-toluene-diethylamine (5:4:2) for the development agent, the thin layer plate is pre-saturated for 20 minutes and then unfolded, taken out, dried, and immediately inspected under a UV lamp (254nm). The position and color of the main spot of the test solution should be consistent with the main spot of the piperaquine phosphate reference solution; Then spray with 2% vanillin in sulfuric acid ethanol solution [vanillin 2G, add 100ml sulfuric acid-ethanol (20-100) mixture to dissolve, I .e., heat at 85°C for 10-20 minutes to clear spots, the position and color of the main spot displayed by the test solution should be consistent with the main spot of the dihydroartemisinin control solution.
- in the chromatogram recorded under the determination of dihydroartemisinin and piperaquine phosphate, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the control solution.
- two items (2) and (3) above can be selected as one item.
examination
- new system for related substances I. Take an appropriate amount of fine powder of this product (about 200mg equivalent to dihydroartemisinin), put it in a 25ml plug Erlenmeyer flask, add 10ml of dichloromethane precisely, shake to dissolve, centrifuge, and filter the supernatant with 0.45um filter, the filtrate was used as the test solution; 1.5ml was accurately measured, placed in a 50ml measuring flask, diluted with dichloromethane to the scale, and used as the control solution (1 ); The control solution (l) was accurately measured. 5ml, in a 100ml measuring flask, diluted to the scale with dichloromethane, as the control solution (2 ) ; In addition, take appropriate amounts of dihydroartemisinin and artemisinin reference products, and weigh them precisely, add dichloromethane to dissolve and dilute to prepare about 20mg of dihydroartemisinin and 0. A mixed solution of 1 mg is used as a system-applicable solution. According to the thin layer chromatography (General 0502) test, absorb the above 4 kinds of solution 10 u1, respectively, on the same silica gel G thin layer plate, with toluene-acetone-glacial acetic acid (90:10:2) for the development of the solvent, spread more than 15cm, take out, dry, spray with 2% vanillin sulfuric acid ethanol solution, heated at 85°C for 10~20 minutes until the spots are clear. In the system applicable solution, dihydroartemisinin and artemisinin should show clearly separated spots, and the control solution (2) should show a single clear spot. No more than 2 impurity spots in the test solution; No more than 1 impurity spot of the same color as the main spot in the control solution (1), and no deeper (3.0%) than the main spot of the control solution (1).
- Related substances II protected from light. Take an appropriate amount of fine powder of this product (about 50mg equivalent to piperaquine), put it in a 100ml measuring flask, add the mobile phase to dissolve and dilute to the scale, shake and filter, the continued filtrate was taken as the test solution. Precision take 3ml 100M l flask, diluted with mobile phase to the scale, shake, as a control solution. The chromatogram was recorded to 3 times of the retention time of the main component peak according to the method for measuring the content of piperaquine phosphate. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (3.0%).
- the dissolution of this product, according to the dissolution and release determination method (General 0931 second method), with hydrochloric acid solution (9-1000)500ml as the dissolution medium, the rotation speed is 75 rpm, according to the law, after 45 minutes, take the solution filtration, take the filtrate.
- dihydroartemisinin the above filtrate was taken as a test solution. Add appropriate amount of dihydroartemisinin reference substance, weigh it precisely, dissolve it with ethanol and dilute it quantitatively to make a solution containing about 0.4mg per 1 ml, shake it well, take 2ml precisely and put it in a 10ml measuring flask, diluted to the scale with dissolution medium, incubated at 37°C for 45 minutes, and allowed to cool as a control solution. Test according to high performance liquid chromatography (General 0512). Silica gel bonded with eighteen alkyl silane was used as the filler; The mobile phase was 0.02mol/L disodium hydrogen phosphate solution (adjusted to pH 2.4 with phosphoric acid)-acetonitrile (65:35); The detection wavelength was 237nm. The theoretical plate number is not less than 3000 according to the calculation of the peak of dihydroartemisinin, and the separation degree of the two peaks of dihydroartemisinin should be greater than 2.0. 5ml of the test solution and 5ml of the reference solution were accurately taken respectively, put in a 25ml measuring flask, dilute with 3.6% sodium hydroxide solution to the scale, shake well, react in a 60°C water bath for 30 minutes, and take out, cool, Precision Add phosphoric acid 0.7ml, shake, filter with 0.45um filter, take 20 u1 in 2 hours, inject human liquid chromatograph, record chromatogram, the dissolution amount of each tablet was calculated by the peak area according to the external standard method. The limit is 70% of the labeled amount and shall be in accordance with the provisions.
- piperaquine phosphate precision take 1 ml of the above filtrate, put it in a 50ml measuring flask, dilute it with dissolution medium until it is calibrated, shake well, and measure it according to UV-Vis spectrophotometry (General rule 0401), the absorbance was measured at a wavelength of 345nm. In addition, an appropriate amount of piperaquine phosphate reference substance was carefully weighed, dissolved and quantitatively diluted with dissolution medium to prepare a solution containing about 12.8ug per lml, which was determined by the same method to calculate the dissolution amount of each tablet. 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
- dihydroartemisinin was determined by HPLC (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler (YMC-Pack ODS-AQ, 4.6mm X 250mm, 5um or equivalent column); Acetonitrile-water (60:40) as mobile phase; The detection wavelength was 216nm. Take the appropriate amount of dihydroartemisinin control and artemisinin control, add acetonitrile-water (8:2) Ultrasonic to dissolve and dilute to prepare a mixed solution containing 1 mg of dihydroartemisinin and artemisinin per 1 ml, 20u1 was injected into human liquid chromatograph, and the chromatogram was recorded. The order of peak was a-dihydroartemisinin, B- dihydroartemisinin and artemisinin, compared with artemisinin peak (retention time is about 10 minutes), the relative retention time of a-dihydroartemisinin is about 0.6, and the separation degree between artemisinin and adjacent dihydroartemisinin peaks should be greater than 2.0.
- A new assay was used. Take 10 tablets of this product, precision weighing, fine grinding, take an appropriate amount (equivalent to dihydroartemisinin about 25mg), Precision weighing, 25ml flask, add acetonitrile-water (6:4) ultrasonic dissolution, cool, dilute to the scale with acetonitrile-water (6:4), shake, centrifuge, take the supernatant as the test solution, record chromatogram with 20m1 injection and record chromatogram. Take about 25mg of dihydroartemisinin reference substance and add acetonitrile-water (6:4). Dissolve and quantitatively dilute to prepare a solution containing about 1 mg per 1 ml, which is determined by the same method. According to the external standard method, the sum of the two peak areas of dihydroartemisinin is obtained.
- maaquine phosphate was measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-0.1% trichloroacetic acid solution-phosphoric acid (20:80:0.035) as mobile phase; The detection wavelength was 349nm. The number of theoretical plates is not less than 1000 based on the piperaquine phosphate peak.
- determination method: take an appropriate amount of the above-mentioned fine powder (about 250mg equivalent to piperaquine phosphate), weigh it accurately, place it in a 100ml measuring flask, add an appropriate amount of mobile phase, dissolve it by ultrasound, and let it cool, dilute to the scale with mobile phase, shake, filter, take the filtrate accurately and put it in a 100ml measuring flask, dilute to the scale with mobile phase, shake well, and use as a test solution, the chromatogram was recorded by injection of 20U1 into human Liquid Chromatograph. The appropriate amount of piperaquine phosphate reference substance was weighed accurately, dissolved and quantitatively diluted with mobile phase to prepare a solution containing about 25ug of piperaquine phosphate per lml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
antimalarial drugs.
storage
shade, Seal, store in a cool and dry place.
Last Update：2022-01-01 11:33:18
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