Avanbulin

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

MedKoo CAT#: 205822

CAS#: 798577-91-0

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.


Chemical Structure

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Avanbulin
CAS# 798577-91-0

Theoretical Analysis

MedKoo Cat#: 205822
Name: Avanbulin
CAS#: 798577-91-0
Chemical Formula: C20H17N7O2
Exact Mass: 387.14437
Molecular Weight: 387.39
Elemental Analysis: C, 62.01; H, 4.42; N, 25.31; O, 8.26

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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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 387.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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



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)