LCR
vincristine
CAS: 57-22-7
Molecular Formula: C46H56N4O10
LCR - Names and Identifiers
| Name | vincristine |
| Synonyms | VCR LCR Onco TCS NSC 67574 NSC-67574 HSDB 3199 CCRIS 5763 Vinkristin NCI-C04864 Vincristine vincristine Vincrystine Leucristine VINCRISTINE Vincristina Vincristinum Leurocristine UNII-5J49Q6B70F Vincristina [DCIT] Leurocristine (7CI, 8CI) Vincristinum [INN-Latin] 22-Oxovincaleukoblastine Vincaleukoblastine, 22-oxo- Vincaleukoblastine, 22-oxo- (9CI) Vincristine ,VCR, NSC-67574, Oncovin (2ξ,2'β,19ξ)-22-oxovincaleukoblastine |
| CAS | 57-22-7 |
| EINECS | 200-318-1 |
| InChI | InChI=1/C46H56N4O10/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/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3/t28-,37?,38?,39-,42+,43-,44?,45+,46+/m1/s1 |
LCR - Physico-chemical Properties
| Molecular Formula | C46H56N4O10 |
| Molar Mass | 824.96 |
| Density | 1.1539 (rough estimate) |
| Melting Point | 211-216 ºC |
| Boling Point | 761.92°C (rough estimate) |
| Specific Rotation(α) | D25 +17°; D25 +26.2° (ethylene chloride) |
| Solubility | Soluble in chloroform, acetone and ethanol. |
| Appearance | White needle crystal |
| pKa | 5.4(at 25℃) |
| Storage Condition | 2-8℃ |
| Stability | Stable, but may be heat sensitive. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.6000 (estimate) |
| Physical and Chemical Properties | White crystals, soluble in methanol, ethanol, DMSO and other organic solvents, from the Vinca. |
| Use | Natural plant antineoplastic drugs for the treatment of acute leukemia and malignant lymphoma, small cell lung cancer and breast cancer |
LCR - Risk and Safety
| UN IDs | 1544 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 i.p. in mice: 5.2 mg/kg (Adamson) |
LCR - Reference
| Reference Show more | 1. Yang Qing, Li Na, Suixin, Li Xiaohua, Shi Xiaozheng, Liu Yingna, Lin, Jia, Nan, Zhang, Hui, yuan, Zhang, Mo. Molecular mechanism of schisandrin B Targeted Regulation of Aβ and downstream NF-κB/TNF-α signaling pathway to protect damaged neurons [J]. Chinese Journal of Traditional Chinese Medicine 2017 32(05):2064-2069. 2. Wei Zhilong di Chong Lou, Meiqing Zhao Yaodong. Schisandrin a reverses the drug resistance of glioma stem/progenitor cells by ATP binding cassette transporter B1 [J]. Chinese Journal of Modern neurological diseases, 2017, 17(06):439-445. 3. Wang Limin, Yang Yu, Zhang Mingyuan, etc. Reversal effect of hyperin on vincristine-resistant colon cancer HCT8/VCR cells [J]. Chinese Journal of Experimental prescriptions, 2016, 022(022):92-96. |
LCR - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| History of discoveries | Canadian doctor Robert Noble is a medical scientist who studies diabetes. When his elder brother Clark Noble (who made a great contribution to the discovery of insulin) heard that "Jamaica treats Vinca as a tea to treat diabetes," he told Robert, and sent him some samples. Like most pharmacologists, Robert also gets information from folk medicine, and then through scientific methods to confirm, and then isolated effective compounds, the development of new drugs. by injecting Vinca extract into the blood of mice and rabbits, they found that Vinca did not actually reduce blood glucose levels. In other words, Vinca has no therapeutic effect on diabetes at all. And then something amazing happened. Careful experimenters found that injection of a sterile Vinca extract caused liver and kidney abscesses in mice. Since there is no bacterial infection, then how can the mice abscess? Further research found that the original vinca extract destroyed the immune system of mice, further research found that Vinca extract directly damaged the spinal cord hematopoietic cells, resulting in reduced immune capacity in the blood. "components in Catharanthus roseus kill white blood cells". A keen Robert was quickly aware of this important finding. Although Vinca extract cannot treat diabetes, it is likely to have a therapeutic effect on leukemia. Now we know that leukemia is due to special reasons for cancer, bone marrow abnormalities, resulting in abnormal white blood cells to multiply. after recognizing the potential effect of Vinca on leukaemia, the keen Robert invited another chemist, Charles Beer, to join in and set out to isolate specific components of the Vinca. In 1958, they finally obtained an active alkaloid, which was named Vinblastine (Vinblastine). At the same time with Robert and Beer in the study of Vinca is also the famous American pharmaceutical company Eli Lily, and later the two team cooperation research and development, the successful launch of our now known anti-cancer medicine-Vincristine (Vincristine). Vincristine has better anticancer effect than vinblastine, and is now the first choice for the treatment of leukemia, especially for acute lymphatic leukemia, Hodgkin's lymphoma and other cancers. |
| pharmacological action | vincristine has anticancer effect, which is about 10 times more effective than vinblastine, it is also effective for other acute leukemias, Hodgkin's disease, lymphosarcoma, reticulocytic sarcoma, and breast cancer. Alkaloids contained in Vinca-Major together with vinblastine, panlorosin, and panloxigenin, etc. It has the effect of stopping cell division (mitosis) in metaphase, which is similar to colchicine, but its effect is stronger than colchicine. Like colchicine, it can bind to tubulin to inhibit its biological activity, but the binding site is different. In addition, it is different from colchicine in that it also acts on proteins other than tubulin, such as actin and 10 nm filament protein. It is used as one of anticancer agents in clinical medicine, and is particularly effective for tumors of hematopoietic organs. Vinblastine sulfate can be used for the treatment of Hodgkin's disease and choriocarcinoma, with good curative effect; For lymphosarcoma, reticular cell sarcoma, acute leukemia (VP,VDLP scheme "V" is vincristine, D is daunorubicin, "L" for asparaginase, "P" For prednisone, breast cancer, nephroblastoma, ovarian cancer, testicular cancer, neuroblastoma and malignant melanoma also have a certain effect. |
| Drug metabolism | vincristine was rapidly distributed in various tissues after intravenous injection, with high concentration in nerve cells, rarely through the blood-brain barrier, cerebrospinal fluid concentration is plasma concentration of 1/30~1/20. Protein binding rate was 75%. In adults, T1/2 is less than 5 minutes, T1/2 is 50 to 155 minutes, and the terminal elimination phase T1/2 is up to 85 hours. Metabolism in the liver, the highest concentration in the bile, mainly with the bile discharge, fecal excretion of 70%, urinary excretion of 5%~ 16%. Vincristine can be selectively concentrated in cancer tissue, can make the proliferation of cells synchronization, and then make the antitumor drug synergistic. |
| indication | ① acute leukemia, especially childhood acute leukemia, has remarkable curative effect on acute lymphoblastic leukemia. malignant lymphoma. ③ germ cell tumor. ④ small cell lung cancer, Ewing's sarcoma, nephroblastoma and neuroblastoma. (5) breast cancer, chronic lymphocytic leukemia, gastrointestinal cancer, melanoma and multiple myeloma. |
| typical adverse reactions | bone marrow suppression, gastrointestinal reaction, nervous system toxicity, thrombophlebitis, alopecia. The main manifestations of nervous system toxicity are numbness of limbs, slow or disappearance of tendon reflex, peripheral neuritis, constipation, paralytic ileus, motor nerve and sensory nerve and cranial nerve symptoms. Repeated intravenous injection can cause thrombophlebitis, leakage to the outside of the blood vessel during injection can cause local necrosis, injection should be stopped immediately, diluted locally with sodium chloride injection; Or local closure with 1% procaine injection, warm wet or cold compress. |
| uses | natural plant antineoplastic agents for the treatment of acute leukemia and malignant lymphoma, small cell lung cancer and breast cancer |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 15:16:51
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