Skip to Content
Merck
CN
All Photos(1)

Documents

Safety Information

V1377

Sigma-Aldrich

Vinblastine sulfate salt

≥97% (HPLC)

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
VLB, Vincaleukoblastine sulfate salt
Empirical Formula (Hill Notation):
C46H58N4O9 · H2SO4
CAS Number:
143-67-9
Molecular Weight:
909.05
Beilstein:
3659812
EC Number:
205-606-0
MDL number:
MFCD00082457
UNSPSC Code:
12352200
PubChem Substance ID:
24278771
NACRES:
NA.77

Quality Level

200

Assay

≥97% (HPLC)

form

(powder or amorphous or crystalline powder)

color

white to light yellow

mp

267 °C (dec.) (lit.)

absorption

14 at 270 nm in 0.1 M phosphate buffer at 1 mM
16.2 at 259 nm in ethanol at 1 mM
53.7 at 214 nm in ethanol at 1 mM

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes

originator

Eli Lilly

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.[H][C@@]12CN(CCc3c([nH]c4ccccc34)[C@@](C1)(C(=O)OC)c5cc6c(cc5OC)N(C)[C@@]7([H])[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67[C@]89[H])C(=O)OC)C[C@](O)(CC)C2

InChI

1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1

InChI key

KDQAABAKXDWYSZ-PNYVAJAMSA-N

Gene Information

human ... TBCC(6903) , TUBA1A(7846) , TUBA1B(10376) , TUBA1C(84790) , TUBA3C(7278) , TUBA3E(112714) , TUBA4A(7277) , TUBB(203068) , TUBB1(81027) , TUBB2A(7280) , TUBB2B(347733) , TUBB3(10381) , TUBB4A(10382) , TUBB4B(10383) , TUBB6(84617) , TUBB8(347688)

Looking for similar products? Visit Product Comparison Guide

Application

Vinblastine sulfate salt has been used:
  • as a microtubule depolymerizing drug for the synchronization of human cell lines in G2/M phase
  • as a multidrug resistance screening substrate in human colon cancer cell line (HCT116) cell line
  • as an antimicrotubule agent in sub perineural glia of Drosophila brain

Biochem/physiol Actions

Plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing self-association in spiral aggregates in a reaction that appears to be regulated by the C-terminus of β-tubulin and is enhanced by GDP and GTP. Depolymerizes microtubules. Arrests the cell cycle in G2/M-phase by blocking mitotic spindle formation. Triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. Substrate of Pgp and CYP3A4.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H341,H361fd

Hazard Classifications

Acute Tox. 4 Oral - Muta. 2 - Repr. 2

WGK

WGK 3

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Phosphorylation of mixed lineage leukemia 5 by CDC2 affects its cellular distribution and is required for mitotic entry
Liu J, et al.
The Journal of Biological Chemistry, 285(27), 20904-20914 (2010)
Mariann Molnár et al.
Scientific reports, 9(1), 14284-14284 (2019-10-05)
In the last decade, avian gene preservation research has focused on the use of the early precursors of the reproductive cells, the primordial germ cells (PGCs). This is because avian PGCs have a unique migration route through the vascular system
Use of drugs to study role of microtubule assembly dynamics in living cells.
M A Jordan et al.
Methods in enzymology, 298, 252-276 (1998-09-30)
DrugTargetSeqR: a genomics-and CRISPR-Cas9-based method to analyze drug targets
Kasap C, et al.
Nature chemical biology, 10(8), 626-626 (2014)
Noelle S Williams et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(7), 2074-2079 (2007-02-09)
Blocking cell division through the inhibition of mitosis is one of the most successful clinical strategies for the treatment of cancer. Taxanes and vinca alkaloids are in widespread use and have demonstrated substantive therapeutic efficacy. Both classes of compounds bind
View All Related Papers

Related Content

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service