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V8388

Sigma-Aldrich

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:
Molecular Weight:
923.04
Beilstein:
3924631
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

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

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General description

Vincristine sulfate is an alkaloid present in Cantharanthus roseus.[00]

Application

Vincristine sulfate has been used:
  • as a positive control in potato disc anti-tumor bioassay
[18]
  • as a standard cytotoxic agent
  • [19]
  • to treat cells for manipulation of the microtubule network
  • [20]
    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).

    Packaging

    1, 5 mg in glass bottle
    25 mg in poly bottle

    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.[00]

    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

    Personal Protective Equipment

    dust mask type N95 (US), Eyeshields, Gloves

    Certificate of Analysis

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    Certificate of Origin

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