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V1377 Sigma-Aldrich

Vinblastine sulfate salt

≥97% (HPLC)

Synonym: VLB, Vincaleukoblastine sulfate salt

  • CAS Number 143-67-9

  • Empirical Formula (Hill Notation) C46H58N4O9 · H2SO4

  • Molecular Weight 909.05

  •  Beilstein/REAXYS Number 3659812

  •  EC Number 205-606-0

  •  MDL number MFCD00082457

  •  PubChem Substance ID 24278771

  •  NACRES NA.77

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Properties

Related Categories Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics T-Z, Antibiotics by Application,
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
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   neoplastics
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)

Description

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 is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

ABC Transporters and Cancer Drug Resistance

Chemotherapy is the treatment of choice against many types of cancer. However, over time chemotherapeutic drugs can become less effective due to the development of resistance that involves a group of...
BioFiles 2007, 2.4, 7.
Keywords: Absorption, Cancer, Clinical, Cloning, Combinatorial synthesis, Diseases, Enzymology, Gene expression, Genetic, Immunology, Pharmaceutical, Reductions, Transfection

Discover Bioactive Small Molecules for ADME/Tox

A significant number of drugs that fail in clinical trials have been associated with safety issues, including unexpected drug-drug interactions (DDI) or lack of efficacy due to poor pharmacokinetics....
Keywords: Absorption, Bioactive small molecules, Clinical, Metabolism

Peer-Reviewed Papers
15

References

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