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
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Formulation: 825 g/mol
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Vincristine (free base) - 57-22-7

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