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Merck
CN

V8879

Vincristine sulfate salt

95.0-105.0% (HPLC), powder or crystals

Synonym(s):

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:
51111767
NACRES:
NA.85
PubChem Substance ID:
57654729
EC Number:
218-190-0
Beilstein/REAXYS Number:
3924631
MDL number:
MFCD00084729

Key Documents

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Product Name

Vincristine sulfate salt, 95.0-105.0% (HPLC), powder or crystals

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 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

biological source

Streptomyces roseosporus

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 light yellow

antibiotic activity spectrum

neoplastics

mode of action

protein synthesis | interferes

storage temp.

−20°C

Quality Level

200

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Analysis Note

Freely soluble in water, Soluble in methanol, slightly soluble in ethanol

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) .

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

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

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000488214
0000465986
0000465986
0000453618
0000453618

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J Renes et al.
British journal of pharmacology, 126(3), 681-688 (1999-04-03)
The present study was performed to investigate the ability of the multidrug resistance protein (MRPI) to transport different cationic substrates in comparison with MDR1-P-glycoprotein (MDR1). Transport studies were performed with isolated membrane vesicles from in vitro selected multidrug resistant cell
Stacey J Baker et al.
Molecular cell, 79(1), 180-190 (2020-07-04)
Rigosertib is a styryl benzyl sulfone that inhibits growth of tumor cells and acts as a RAS mimetic by binding to Ras binding domains of RAS effectors. A recent study attributed rigosertib's mechanism of action to microtubule binding. In that
Moutushy Mitra et al.
Investigative ophthalmology & visual science, 52(8), 5441-5448 (2011-05-07)
To explore the possibility of stathmin as an effective therapeutic target and to evaluate the synergistic combination of stathmin RNAi and the antimicrotubule agents paclitaxel and vincristine to retinoblastoma Y79 cells. RNAi-mediated specific inhibition of stathmin expression in Y79 cells
Patrick J Stiff et al.
The New England journal of medicine, 369(18), 1681-1690 (2013-11-01)
The efficacy of autologous stem-cell transplantation during the first remission in patients with diffuse, aggressive non-Hodgkin's lymphoma classified as high-intermediate risk or high risk on the International Prognostic Index remains controversial and is untested in the rituximab era. We treated
Richard Delarue et al.
The Lancet. Oncology, 14(6), 525-533 (2013-04-13)
Immunochemotherapy with rituximab and cyclophosphamide, doxorubicin, vincristine, and prednisone (R-CHOP) has become the standard of care for elderly patients with diffuse large B-cell lymphoma. We aimed to ascertain if a dose-dense R-CHOP regimen administered every 2 weeks (R-CHOP14) was superior
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