Avanbulin

WARNING: This product is for research use only, not for human or veterinary use.

Description:Avanbulin, also known as BAL27862, is a novel synthetic potent inhibitor of tubulin polymerization that induces cancer cell death. BAL27862 is a novel microtubule-destabilizing drug that is currently undergoing phase I clinical evaluation as the prodrug BAL101553. BAL27862 elicits a unique microtubule (MT) phenotype, distinct from paclitaxel, vinblastine and colchicine, has broad in vitro anti-proliferative activity against a diverse range of human tumor lines (low nM IC50s) and induces significant antitumor responses in a range.

Price and Availability

Avanbulin, purity > 98% is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 205822Name: AvanbulinCAS#: 798577-91-0Chemical Formula: C20H17N7O2Exact Mass: 387.14437Molecular Weight: 387.39Elemental Analysis: C, 62.01; H, 4.42; N, 25.31; O, 8.26

Synonym:BAL27862; BAL-27862; BAL 27862; Avanbulin

IUPAC/Chemical Name:3-((4-(1-(2-(4-aminophenyl)-2-oxoethyl)-1H-benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-yl)amino)propanenitrile

InChi Key:LSFOZQQVTWFMNS-UHFFFAOYSA-N

InChi Code:InChI=1S/C20H17N7O2/c21-10-3-11-23-19-18(25-29-26-19)20-24-15-4-1-2-5-16(15)27(20)12-17(28)13-6-8-14(22)9-7-13/h1-2,4-9H,3,11-12,22H2,(H,23,26)

SMILES Code:N#CCCNC1=NON=C1C2=NC3=CC=CC=C3N2CC(C4=CC=C(N)C=C4)=O

Technical Data

Additional Information

BAL27862 is a novel MTA that triggers apoptosis in cancer cells. In vitro, BAL27862 destabilizes microtubules to produce a microtubule phenotype distinct from that observed with other MTAs, and retains its antiproliferative activity against P-gp overexpressing tumor cells. BAL27862, when administered intravenously or orally, induces significant antitumor responses in a range of animal models of human cancer, including tumors refractory to conventional treatments. BAL27862 overcomes P-gp overexpression-mediated resistance, and demonstrate that Bcl-2 status and tubulin modifications do not necessarily affect its antitumor activity. Analysis of MDs shows that BAL27862 elicited effects consistent with its destabilizing activity; suppression of MDs was 2-fold lower than observed with PTX. Strikingly, BAL27862 displayed a unique microtubule severing activity. Conclusions: Besides its microtubule-targeting activity, BAL27862 displays unique features in its mechanism of action that make it a promising compound for clinical investigation.  (source: J Clin Oncol 28, 2010 (suppl; abstr e13589)   

References

1: Prota AE, Danel F, Bachmann F, Bargsten K, BueyRM, Pohlmann J, Reinelt S, Lane H, Steinmetz MO. The novelmicrotubule-destabilizing drug BAL27862 binds to  the colchicinesite of tubulin with distinct effects on microtubule organization. J MolBiol. 2014 Apr 17;426(8):1848-60. doi: 10.1016/j.jmb.2014.02.005. Epub2014 Feb 11. PubMed PMID: 24530796.