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V8388

Sigma-Aldrich

Vincristine sulfate

meets USP testing specifications

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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/REAXYS Number:
3924631
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

agency

USP/NF
meets USP testing specifications

Quality Level

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

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1 of 4

This Item
V8879PHR17151714007
vibrant-m

V8388

Vincristine sulfate

vibrant-m

V8879

Vincristine sulfate salt

vibrant-m

PHR1715

Sisomicin Sulfate

vibrant-m

1714007

Vincristine sulfate

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

neoplastics

antibiotic activity spectrum

-

antibiotic activity spectrum

-

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

-

mode of action

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-10 to -25°C

storage temp.

−20°C

solubility

ethanol: slightly soluble, water: freely soluble, methanol: soluble

solubility

-

solubility

-

solubility

-

agency

USP/NF

agency

-

agency

traceable to Ph. Eur. S0660000, traceable to USP 1612801

agency

-

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.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

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

ppe

Eyeshields, Gloves, type N95 (US)


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