V8879

Vincristine sulfate salt

95.0-105.0% (HPLC), powder or crystals

• Synonym(s): 22-Oxovincaleukoblastine sulfate salt, Leurocristine sulfate salt, VCR
• Empirical Formula (Hill Notation): C₄₆H₅₆N₄O₁₀ · H₂SO₄
• CAS Number: 2068-78-2
• Molecular Weight: 923.04
• Beilstein/REAXYS Number: 3924631
• EC Number: 218-190-0
• MDL number: MFCD00084729
• UNSPSC Code: 51111767
• PubChem Substance ID: 57654729
• NACRES: NA.85

Properties

• biological source: Streptomyces roseosporus
• assay: 95.0-105.0% (HPLC)
• form: powder or crystals
• storage condition: (Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)
• color: white to light yellow
• antibiotic activity spectrum: neoplastics
• 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

Application

Vincristine is an antitumor alkaloid isolated from Vinca Rosea. It is used to treat acute leukaemia, malignant lymphoma, Hodgkin′s disease, acute erythraemia, acute panmyelosis, breast cancer, Kaposi′s sarcoma and testicular cancer. Vincristine is widely used in cancer research. It is used to study multi-drug resistance. It is used to inhibit cell cycle progression at M-phase and to inhibit monoamine oxidase (MAO) .

Biochem/physiol Actions

Vincristine is a plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing coiled spiral aggregate formation. It arrests cell cycle in G2/M-phase by blocking mitotic spindle formation. Vincristine triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. It inhibits VEGF production in leukemia cell lines. It is a substrate for Pgp and CYP3A4. MRP1 transports vincristine in an ATP- and GSH-dependent manner. Vincristine has some immunosuppressant effect. Vincristine may also interfere with amino acid, cyclic AMP, and glutathione metabolism, calmodulin-dependent Ca2+-transport, cellular respiration, and nucleic acid and lipid biosynthesis.

Analysis Note

Freely soluble in water, Soluble in methanol, slightly soluble in ethanol

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H341,H361fd
• pcodes: P202 - P264 - P270 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 2 Oral - Muta. 2 - Repr. 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable