Verubulin

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

MedKoo CAT#: 201960

CAS#: 827031-83-4

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.


Chemical Structure

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Verubulin
CAS# 827031-83-4

Theoretical Analysis

MedKoo Cat#: 201960
Name: Verubulin
CAS#: 827031-83-4
Chemical Formula: C17H17N3O
Exact Mass: 279.13716
Molecular Weight: 279.34
Elemental Analysis: C, 73.10; H, 6.13; N, 15.04; O, 5.73

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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

Appearance: White 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 279.34 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: Mahal K, Resch M, Ficner R, Schobert R, Biersack B, Mueller T. Effects of the Tumor-Vasculature-Disrupting Agent Verubulin and Two Heteroaryl Analogues on Cancer Cells, Endothelial Cells, 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 I trial of verubulin (MPC-6827) plus carboplatin in patients with relapsed glioblastoma 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 toxicity profiles 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. Phase I clinical trial of MPC-6827 (Azixa), a microtubule destabilizing agent, in patients with advanced cancer. Mol Cancer Ther. 2010 Dec;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, Anderson MB, Mather G, Pleiman CM, Kasibhatla S, Tseng B, Drewe J, Cai SX. Discovery of N-methyl-4-(4-methoxyanilino)quinazolines as potent apoptosis inducers. Structure-activity relationship of the quinazoline ring. 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. Discovery of N-(4-methoxyphenyl)-N,2-dimethylquinazolin-4-amine, a potent apoptosis inducer and efficacious anticancer agent with high blood brain barrier 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 microtubule formation that is not a substrate for multidrug resistance pumps. Cancer Res. 2007 Jun 15;67(12):5865-71. PubMed PMID: 17575155.



Additional Information

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