Vincristine - 57-22-7

Vincristine

Catalog Number: EVT-254418
CAS Number: 57-22-7
Molecular Formula: C46H56N4O10
Molecular Weight: 825 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
Vincristine is a natural alkaloid that is derived from the Madagascar periwinkle plant, Catharanthus roseus. It is a potent anticancer drug that is widely used in the treatment of various types of cancer, including leukemia, lymphoma, and solid tumors. Vincristine works by disrupting the microtubule formation in cancer cells, which inhibits their ability to divide and grow.
Applications in Various Fields
Vincristine has several applications in medical, environmental, and industrial research. In medical research, vincristine plays a crucial role in drug development and clinical trials. It is also used in combination with other anticancer drugs to improve their efficacy. In environmental research, vincristine is used to study its effects on ecosystems and its role in pollution management. In industrial research, vincristine is used in manufacturing processes to improve product quality and efficiency.
Benefits and potential side effects:
The benefits of vincristine in cancer treatment are significant, as it is a potent anticancer drug that can improve patient outcomes. However, its potential side effects, such as peripheral neuropathy and bone marrow suppression, can be severe and require careful monitoring and management.

Properties

CAS Number

57-22-7

Product Name

Vincristine

IUPAC Name

methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15S,17S)-17-ethyl-17-hydroxy-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-8-formyl-10-hydroxy-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

Molecular Formula

C46H56N4O10

Molecular Weight

825 g/mol

InChI

InChI=1S/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

InChI Key

OGWKCGZFUXNPDA-XQKSVPLYSA-N

SMILES

CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O

Solubility

In water, 2.27 mg/L at 25 °C (est)
3.00e-02 g/L

Synonyms

cellcristin
Citomid
Farmistin
Leurocristine
Oncovin
Oncovine
Onkocristin
PFS, Vincasar
Sulfate, Vincristine
Vincasar
Vincasar PFS
Vincristin Bristol
Vincristin medac
Vincristine
Vincristine Sulfate
Vincrisul
Vintec

Canonical SMILES

CCC1(CC2CC(C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O

Isomeric SMILES

CC[C@@]1(C[C@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O
Method of Synthesis or Extraction
Vincristine is extracted from the leaves of the Catharanthus roseus plant. The extraction process involves the use of solvents such as methanol, ethanol, or chloroform to extract the alkaloids from the plant material. The extracted alkaloids are then purified using various chromatographic techniques such as column chromatography, thin-layer chromatography, and high-performance liquid chromatography.
Efficiency and yield of each method:
The efficiency and yield of the extraction process depend on various factors such as the quality of the plant material, the type of solvent used, and the purification techniques employed. The yield of vincristine from the plant material is typically low, ranging from 0.0003% to 0.001%. However, the use of advanced extraction and purification techniques can improve the yield and efficiency of the process.
Environmental and safety considerations:
The extraction and purification of vincristine from the Catharanthus roseus plant can have environmental and safety implications. The use of solvents such as chloroform can be hazardous to the environment and human health. Therefore, it is essential to use environmentally friendly solvents and adopt safe handling practices to minimize the environmental and safety risks associated with the extraction process.
Chemical Structure and Biological Activity
Vincristine has a complex chemical structure that consists of a tetracyclic indole alkaloid ring system. The molecule contains a vinyl group, an N-methyl group, and a catharanthine moiety. The biological activity of vincristine is primarily attributed to its ability to disrupt microtubule formation in cancer cells. This mechanism of action inhibits cell division and growth, leading to the death of cancer cells.
Biological Effects
Vincristine has several biological effects on cell function and signal transduction. It disrupts the microtubule formation in cancer cells, leading to the inhibition of cell division and growth. Vincristine also affects the function of the nervous system, leading to peripheral neuropathy, which is a common side effect of the drug. In addition, vincristine can cause bone marrow suppression, which can lead to anemia, thrombocytopenia, and neutropenia.
Potential therapeutic and toxic effects:
Vincristine has potent anticancer activity and is widely used in the treatment of various types of cancer. However, it can also have toxic effects on normal cells, leading to side effects such as peripheral neuropathy, bone marrow suppression, and gastrointestinal disturbances. Therefore, the use of vincristine in cancer treatment requires careful monitoring and management of its potential toxic effects.
Future Perspectives and Challenges
The use of vincristine in cancer treatment faces several challenges, such as its potential toxic effects and the development of drug resistance. Therefore, future research should focus on developing new drugs that can overcome these challenges and improve patient outcomes. In addition, the use of vincristine in environmental and industrial research requires careful consideration of its potential environmental and safety implications.
Conclusion:
Vincristine is a potent anticancer drug that is widely used in the treatment of various types of cancer. Its mechanism of action involves the disruption of microtubule formation in cancer cells, leading to the inhibition of cell division and growth. The extraction and purification of vincristine from the Catharanthus roseus plant can have environmental and safety implications, and the use of the drug in cancer treatment requires careful monitoring and management of its potential toxic effects. Future research should focus on developing new drugs that can overcome the challenges associated with the use of vincristine in cancer treatment.

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