VINCRISTINE SULPHATE
Vincristine sulfate
CAS: 2068-78-2
Molecular Formula: C46H58N4O14S
VINCRISTINE SULPHATE - Names and Identifiers
| Name | Vincristine sulfate |
| Synonyms | VCR VCR SULFATE Vincristine sulfate VINCRISTINE SULFATE Vincristine Sulphate VINCRISTINE SULPHATE VINCRISTINE SULFATE SALT Vincristine sulfate salt VCR, LEUKOCRISTINE SULFATE Leurocristine sulfate salt Vincristine Sulfate, Apocynaceae sp. 22-Oxovincaleukoblastine sulfate salt VINCRISTINE SULFATE, APOCYNACEAE SPECIES (2alpha,2'beta,3alpha,4alpha,5beta,19beta)-22-oxovincaleukoblastine (2alpha,3alpha,4alpha,5beta,19beta)-22-oxovincaleukoblastine sulfate (2alpha,2'beta,3alpha,4alpha,5beta,19beta)-22-oxovincaleukoblastine sulfate |
| CAS | 2068-78-2 |
| EINECS | 218-190-0 |
| InChI | InChI=1/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28?,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1 |
VINCRISTINE SULPHATE - Physico-chemical Properties
| Molecular Formula | C46H58N4O14S |
| Molar Mass | 923.04 |
| Melting Point | 300 °C |
| Boling Point | 273-281 °C |
| Specific Rotation(α) | D26 +8.5° (c = 0.8) |
| Water Solubility | >=1 g/100 mL at 24 ºC |
| Solubility | Soluble in water, insoluble in petroleum ether. |
| Appearance | White crystal |
| Color | white to off-white |
| BRN | 3924631 |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months. |
| MDL | MFCD00084729 |
| Physical and Chemical Properties | Melting point 273-281°C water-soluble> = 1g/100 mL at 24°C |
VINCRISTINE SULPHATE - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R61 - May cause harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. R63 - Possible risk of harm to the unborn child R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R68 - Possible risk of irreversible effects R62 - Possible risk of impaired fertility R25 - Toxic if swallowed |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | OH6340000 |
| FLUKA BRAND F CODES | 8-10 |
| HS Code | 29399990 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 intraperitoneal in mouse: 3mg/kg |
VINCRISTINE SULPHATE - Reference Information
| (IARC) carcinogen classification | 3 (Vol. 26, Sup 7) 1987 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | Vincristine (Vincristine), trade name "Viscine", "Ankeping" (Oncovin), also known as vincristine, Neovinblastine, medically referred to as VCR, is an alkaloid extracted from periwinkle, a plant of the genus Oleaceae. It is a mitotic inhibitor that is widely used in chemotherapy to treat a variety of cancers, including acute lymphoblastic leukemia, acute myeloid leukemia, Hodgkin's lymphoma, neuroblastoma, and small cell lung cancer. Vincristine sulfate is its sulfate form. |
| pharmacological action | vincristine sulfate (vincristinesulfate,VCR) is a cell cycle specific anti-tumor drug of periwinkle alkaloids of Apocynaceae. The anti-tumor target is microtubules, which mainly inhibit the polymerization of tubulin and affect the formation of spindle microtubules, so that mitosis stops in the metaphase. |
| clinical application | like other periwinkle alkaloids, VCR has a good therapeutic effect on many malignant tumors of lymphoid tissues, including invasive non-Hodgkin lymphoma and acute lymphoblastic leukemia. It is mainly used in the treatment of acute leukemia, malignant lymphoma, neuroblastoma, chronic lymphocytic leukemia and other diseases. |
| prepare | 2g of vinblastine sulfate dissolved in 240ml of tetrahydrofuran, add 7.5ml of glacial acetic acid, under its protection, cool down to -65 ℃ with dry ice, under stirring, add the prepared sodium dicadmium solution (3g of sodium dicadmium dissolved in 15ml of water, then add 2ml of concentrated sulfuric acid, stir and dissolve), the reaction temperature is maintained below -50°C during the dropping process. After dropping, stir and react at -65 ℃ for 3 hours. pour the reaction solution into a mixed solution of 35ml of concentrated ammonia water and 200ml of water, extract with 600ml of dichloromethane, dry with anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain 2.06g of crude vincristine, and the purity is 83% detected by HPLC. the obtained crude vincristine is dissolved in 20ml of isopropanol, stirred, 16ml of 1% isopropanol sulfate solution is added dropwise to filter out the solid when the PH is adjusted to be ≤ 4, and is dried in vacuum to obtain 1.82g of crude vincristine sulfate. the purity is 92% detected by HPLC. dissolve 1.8g of crude vincristine sulfate in 36ml of absolute ethanol, cool to -10 ℃, stir slowly, precipitate solid, filter, wash with absolute ethanol, and dry in vacuum to obtain 1.63g of vincristine sulfate with 81.5% yield and 98.6% purity detected by HPLC. |
| use | sulfate of a natural alkaloid, isolated from plant vincristine, has anti-mitotic and anti-tumor activities. Vincristine irreversibly binds to microtubules and spindle proteins in the S phase of the cell cycle, interfering with the formation of mitotic spindles, thereby inhibiting tumor cells in the metaphase. The microtubules are depolymerized and may interfere with the metabolism of amino acids, cyclic adenosine monophosphate and glutathione. Natural plant anti-tumor drugs are used to treat acute leukemia and malignant lymphoma, small cell lung cancer and breast cancer. It is widely used in cancer research, multi-drug inhibition and monoamine oxidase (monoamine oxidase) inhibitor. |
Last Update：2024-04-09 19:05:10
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