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Merck

V8388

Vincristine sulfate

meets USP testing specifications

Synonym(s):

Vincristine sulfate salt, 22-Oxovincaleukoblastine sulfate salt, Leurocristine sulfate salt, VCR

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About This Item

Empirical Formula (Hill Notation):
C46H56N4O10 · H2SO4
CAS Number:
2068-78-2
Molecular Weight:
923.04
UNSPSC Code:
12352210
NACRES:
NA.21
PubChem Substance ID:
24900771
EC Number:
218-190-0
Beilstein/REAXYS Number:
3924631
MDL number:
MFCD00084729

Product Name

Vincristine sulfate, meets USP testing specifications

InChI key

AQTQHPDCURKLKT-PNYVAJAMSA-N

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

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

agency

USP/NF
meets USP testing specifications

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

Quality Level

200

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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.

General description

Vincristine sulfate is an alkaloid present in Cantharanthus roseus.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000453617
0000453617
0000389773
0000332138
0000308038

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