V8388

Vincristine sulfate

meets USP testing specifications

• Synonym(s): Vincristine sulfate salt, 22-Oxovincaleukoblastine sulfate salt, Leurocristine sulfate salt, VCR
• Empirical Formula (Hill Notation): C₄₆H₅₆N₄O₁₀ · H₂SO₄
• CAS Number: 2068-78-2
• Molecular Weight: 923.04
• Beilstein: 3924631
• EC Number: 218-190-0
• MDL number: MFCD00084729
• PubChem Substance ID: 24900771
• NACRES: NA.21

Properties

• Agency: USP/NF; meets USP testing specifications
• Quality Level: 200
• solubility: ethanol: slightly soluble; methanol: soluble; water: freely soluble
• antibiotic activity spectrum: neoplastics
• application(s): pharmaceutical (small molecule)
• Mode of action: protein synthesis | interferes
• storage temp.: −20°C
• SMILES string: OS(O)(=O)=O.CC[C@]1(O)CC2CN(CCc3c([nH]c4ccccc34)[C@@](C2)(C(=O)OC)c5cc6c(cc5OC)N(C=O)C7[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67C89)C(=O)OC)C1
• InChI: 1S/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
• InChI key: AQTQHPDCURKLKT-PNYVAJAMSA-N

Description

General description

Vincristine sulfate is an alkaloid present in Cantharanthus roseus.

Application

Vincristine sulfate has been used:

• as a positive control in potato disc anti-tumor bioassay
• as a standard cytotoxic agent
• to treat cells for manipulation of the microtubule network

Widely used in cancer research. In studies on multi-drug resistance. Used to inhibit cell cycle progression at M-phase. Used to inhibit monoamine oxidase (MAO).

Biochem/physiol Actions

Vincristine sulfate possesses antitumor action targeting cell cycle. It prevents the action of tubulin by inhibiting microtubule polymerization. It also causes cell death and blocks metaphase in mitosis by preventing chromosome segregation. Vincristine sulfate inhibits angiogenesis mediated by factors such as vasculature endothelial growth factor. It decreases vascularization in tumors and normal tissues.

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300 - H341 - H361fd
• Precautionary Statements: P202 - P264 - P270 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 2 Oral - Muta. 2 - Repr. 2
• Storage Class Code: 6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves