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V8879

Sigma-Aldrich

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:
Molecular Weight:
923.04
Beilstein:
3924631
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces roseosporus

Quality Level

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 slightly 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

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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) .

Packaging

1, 5, 25 mg in glass bottle

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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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