V1377

Vinblastine sulfate salt

≥97% (HPLC), powder, plant alkaloid

• 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

Properties

• product name: Vinblastine sulfate salt, ≥97% (HPLC)
• 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)

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

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302,H341,H361fd
• Precautionary Statements: P201 - P301 + P312 + P330 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Muta. 2 - Repr. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3