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V8388

Sigma-Aldrich

Vincristine sulfate

meets USP testing specifications

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

Quality Level

Agency

USP/NF
meets USP testing specifications

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.

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).

Packaging

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

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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