Vincristine (free base)
White to off-white, odorless amorphous or crystalline powder
Inhibitors
Vincristine is a natural alkaloid isolated from the plant Vinca rosea Linn. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca++ -transport ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis. (NCI04)
Vincristine, also known as VIN or leurocristine, belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together. Vincristine exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Vincristine has been detected in multiple biofluids, such as urine and blood. Within the cell, vincristine is primarily located in the cytoplasm and membrane (predicted from logP). Vincristine participates in a number of enzymatic reactions. In particular, Vincristine can be converted into vincristine through the action of the enzyme multidrug resistance protein 1. In addition, Vincristine can be converted into vincristine; which is mediated by the enzyme rala-binding protein 1. In humans, vincristine is involved in the vincristine action pathway. Vincristine is a potentially toxic compound.
Vincristine is a vinca alkaloid with formula C46H56N4O10 found in the Madagascar periwinkle, Catharanthus roseus. It is used (commonly as the corresponding sulfate salt)as a chemotherapy drug for the treatment of leukaemia, lymphoma, myeloma, breast cancer and head and neck cancer. It has a role as a tubulin modulator, a microtubule-destabilising agent, a plant metabolite, an antineoplastic agent and a drug. It is a methyl ester, an acetate ester, a tertiary alcohol, a member of formamides, an organic heteropentacyclic compound, an organic heterotetracyclic compound, a tertiary amino compound and a vinca alkaloid. It is a conjugate base of a vincristine(2+). It derives from a hydride of a vincaleukoblastine. 825 g/mol
Vincristine, also known as VIN or leurocristine, belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together. Vincristine exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Vincristine has been detected in multiple biofluids, such as urine and blood. Within the cell, vincristine is primarily located in the cytoplasm and membrane (predicted from logP). Vincristine participates in a number of enzymatic reactions. In particular, Vincristine can be converted into vincristine through the action of the enzyme multidrug resistance protein 1. In addition, Vincristine can be converted into vincristine; which is mediated by the enzyme rala-binding protein 1. In humans, vincristine is involved in the vincristine action pathway. Vincristine is a potentially toxic compound.
Vincristine is a vinca alkaloid with formula C46H56N4O10 found in the Madagascar periwinkle, Catharanthus roseus. It is used (commonly as the corresponding sulfate salt)as a chemotherapy drug for the treatment of leukaemia, lymphoma, myeloma, breast cancer and head and neck cancer. It has a role as a tubulin modulator, a microtubule-destabilising agent, a plant metabolite, an antineoplastic agent and a drug. It is a methyl ester, an acetate ester, a tertiary alcohol, a member of formamides, an organic heteropentacyclic compound, an organic heterotetracyclic compound, a tertiary amino compound and a vinca alkaloid. It is a conjugate base of a vincristine(2+). It derives from a hydride of a vincaleukoblastine. 825 g/mol
Formulation:
825 g/mol
Source:
Usage:
Vincristine (free base)
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-254418
CAS Number: 57-22-7
Molecular Formula: C46H56N4O10
Molecular Weight: 825 g/mol
| CAS Number | 57-22-7 |
|---|---|
| Product Name | Vincristine (free base) |
| Molecular Formula | C46H56N4O10 |
| Molecular Weight | 825 g/mol |
| Appearance | White to off-white, odorless amorphous or crystalline powder |
| Colorform | Blades from methanol |
| Impurities | 3'-hydroxyvincristine; 4'-deoxyvincristine; N-desmethylvinblastine; deacetylvincristine; deacetylvinblastine; vinblastine; leurosine; formylleurosine |
| 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 |
| 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 |
| IUPAC Name | methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(13S,15R,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 |
| 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 |
| Description | Vincristine is a natural alkaloid isolated from the plant Vinca rosea Linn. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca++ -transport ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis. (NCI04) Vincristine, also known as VIN or leurocristine, belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together. Vincristine exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Vincristine has been detected in multiple biofluids, such as urine and blood. Within the cell, vincristine is primarily located in the cytoplasm and membrane (predicted from logP). Vincristine participates in a number of enzymatic reactions. In particular, Vincristine can be converted into vincristine through the action of the enzyme multidrug resistance protein 1. In addition, Vincristine can be converted into vincristine; which is mediated by the enzyme rala-binding protein 1. In humans, vincristine is involved in the vincristine action pathway. Vincristine is a potentially toxic compound. Vincristine is a vinca alkaloid with formula C46H56N4O10 found in the Madagascar periwinkle, Catharanthus roseus. It is used (commonly as the corresponding sulfate salt)as a chemotherapy drug for the treatment of leukaemia, lymphoma, myeloma, breast cancer and head and neck cancer. It has a role as a tubulin modulator, a microtubule-destabilising agent, a plant metabolite, an antineoplastic agent and a drug. It is a methyl ester, an acetate ester, a tertiary alcohol, a member of formamides, an organic heteropentacyclic compound, an organic heterotetracyclic compound, a tertiary amino compound and a vinca alkaloid. It is a conjugate base of a vincristine(2+). It derives from a hydride of a vincaleukoblastine. |
| Melting Point | 424 to 428 °F (NTP, 1992) 220 °C 218-220 °C |
| Other CAS Number | 57-22-7 |
| Physical Description | Vincristine appears as a white crystalline solid. Melting point 218°C. Used as an antineoplastic. Solid |
| Shelf Life | STERILE SOLN IN EITHER H2O OR PHYSIOLOGICAL SALINE STORED IN REFRIGERATOR FOR UP TO 2 WK WITHOUT SIGNIFICANT LOSS OF POTENCY |
| 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 |
| PubChem Compound | Vincristine (free base) |
| Last Modified | Apr 08 2022 |