Verubulin

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

Description:Verubulin, also known as MPC-6827, is a quinazoline derivative with potential dual antineoplastic activities. Verubulin binds to and inhibits tubulin polymerization and interrupts microtubule formation, resulting in disruption of mitotic spindle assembly, cell cycle arrest in the G2/M phase, and cell death.MPC-6827 appears to disrupt tumor microvasculature specifically, which may result in acute ischemia and massive tumor cell death.

Price and Availability

Verubulin is not in stock, but 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#: 201960Name: VerubulinCAS#: 827031-83-4Chemical Formula: C17H17N3OExact Mass: 279.13716Molecular Weight: 279.34Elemental Analysis:C, 73.10; H, 6.13; N, 15.04; O, 5.73

Synonym:MPC6827; MPC-6827; MPC 6827; MX128495; MX-128495; MX 128495; EP90745; EP-90745;EP 90745; Verubulin; trade name: Azixa

IUPAC/Chemical Name:N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine

InChi Key:SNHCRNMVYDHVDT-UHFFFAOYSA-N

InChi Code:InChI=1S/C17H17N3O/c1-12-18-16-7-5-4-6-15(16)17(19-12)20(2)13-8-10-14(21-3)11-9-13/h4-11H,1-3H3

SMILES Code:CC1=NC(N(C2=CC=C(OC)C=C2)C)=C3C=CC=CC3=N1

Technical Data

Additional Information

Related CAS#917369-31-4 (Verubulin hydrochloride)827031-83-4 (Verubulin)  

References

1: Mahal K, Resch M, Ficner R, Schobert R, BiersackB, Mueller T. Effects of the Tumor-Vasculature-Disrupting AgentVerubulin and Two Heteroaryl Analogues on Cancer Cells, EndothelialCells, and Blood Vessels. ChemMedChem. 2014 Feb 23. doi:10.1002/cmdc.201300531. [Epub ahead of print] PubMed PMID: 24678059.

2: Grossmann KF, Colman H, Akerley WA, Glantz M, Matsuoko Y, Beelen AP,Yu M, De Groot JF, Aiken RD, Olson JJ, Evans BA, Jensen RL. Phase Itrial of verubulin (MPC-6827) plus carboplatin in patients with relapsedglioblastoma multiforme. J Neurooncol. 2012 Nov;110(2):257-64. doi:10.1007/s11060-012-0964-7. Epub 2012 Aug 30. Erratum in: J Neurooncol.2013 May;113(1):151. Olsen, Jeffery J [corrected to Olson, Jeffrey J].PubMed PMID: 22932984.

3: Subbiah IM, Lenihan DJ, Tsimberidou AM. Cardiovascular toxicityprofiles of vascular-disrupting agents. Oncologist. 2011;16(8):1120-30.doi: 10.1634/theoncologist.2010-0432. Epub 2011 Jul 8. PubMed PMID:21742963; PubMed Central PMCID: PMC3228163.

4: Tsimberidou AM, Akerley W, Schabel MC, Hong DS, Uehara C, Chhabra A,Warren T, Mather GG, Evans BA, Woodland DP, Swabb EA, Kurzrock R. PhaseI clinical trial of MPC-6827 (Azixa), a microtubule destabilizing agent,in patients with advanced cancer. Mol Cancer Ther. 2010Dec;9(12):3410-9. doi: 10.1158/1535-7163.MCT-10-0516. PubMed PMID:21159616.

5: Sirisoma N, Pervin A, Zhang H, Jiang S, Adam Willardsen J, AndersonMB, Mather G, Pleiman CM, Kasibhatla S, Tseng B, Drewe J, Cai SX.Discovery of N-methyl-4-(4-methoxyanilino)quinazolines as potentapoptosis inducers. Structure-activity relationship of the quinazolinering. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2330-4. doi:10.1016/j.bmcl.2010.01.155. Epub 2010 Feb 4. PubMed PMID: 20188546.

6: Sirisoma N, Pervin A, Zhang H, Jiang S, Willardsen JA, Anderson MB,Mather G, Pleiman CM, Kasibhatla S, Tseng B, Drewe J, Cai SX. Discoveryof N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potentapoptosis inducer and efficacious anticancer agent with high blood brainbarrier penetration. J Med Chem. 2009 Apr 23;52(8):2341-51. doi:10.1021/jm801315b. PubMed PMID: 19296653.

7: Kasibhatla S, Baichwal V, Cai SX, Roth B, Skvortsova I, Skvortsov S,Lukas P, English NM, Sirisoma N, Drewe J, Pervin A, Tseng B, Carlson RO,Pleiman CM. MPC-6827: a small-molecule inhibitor of microtubuleformation that is not a substrate for multidrug resistance pumps. CancerRes. 2007 Jun 15;67(12):5865-71. PubMed PMID: 17575155.