Synonym
BNC105P; BNC 105P; BNC-105P
IUPAC/Chemical Name
sodium 6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzofuran-7-yl phosphate
InChi Key
VVIPLWCZZYERCA-UHFFFAOYSA-L
InChi Code
InChI=1S/C20H21O10P.2Na/c1-10-16(17(21)11-8-14(26-3)19(28-5)15(9-11)27-4)12-6-7-13(25-2)20(18(12)29-10)30-31(22,23)24;;/h6-9H,1-5H3,(H2,22,23,24);;/q;2*+1/p-2
SMILES Code
O=P([O-])([O-])OC1=C(OC(C)=C2C(C3=CC(OC)=C(OC)C(OC)=C3)=O)C2=CC=C1OC.[Na+].[Na+]
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
>5 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
More Info
BNC105P is the disodium phosphate ester prodrug of BNC105, a tubulin polymerization inhibitor (TPI) that exhibits a high degree of selectivity for tumor endothelial cells. BNC105P disrupts the vasculature within solid tumors in mice and acts as a direct antiproliferative, suppressing tumor cell growth in culture. BNC105P shows evidence of good efficacy in mice-bearing xenografts of several human-tumor types, causing the regression of tumors, and in some cases tumor clearance. Evaluations in preclinical models of cancer have shown that BNC105P is more potent and displays a significantly improved therapeutic index compared with other VDAs in development . BNC105P achieves >95% vascular disruption as early as 3 hours post administration in tumor bearing mice when dosed at 10 mg/kg. This dose is well tolerated as a Day 1, Day 8 dose in a 21-day treatment cycle. (source: Clin Cancer Res. 2011 Aug 1;17(15):5152-60.).
BNC105P and BNC-105 are analogues of CA4 and CA4P their structures are showed as the following:
Source: Clin Cancer Res. 2011 Aug 1;17(15):5152-60.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
452.35
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.
| 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 |
1: Flynn BL, Gill GS, Grobelny DW, Chaplin JH, Paul D, Leske AF, Lavranos TC, Chalmers DK, Charman SA, Kostewicz E, Shackleford DM, Morizzi J, Hamel E, Jung MK, Kremmidiotis G. Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties. J Med Chem. 2011 Sep 8;54(17):6014-27. doi: 10.1021/jm200454y. Epub 2011 Aug 5. PubMed PMID: 21774499; PubMed Central PMCID: PMC3172808.
2: Rischin D, Bibby DC, Chong G, Kremmidiotis G, Leske AF, Matthews CA, Wong SS, Rosen MA, Desai J. Clinical, pharmacodynamic, and pharmacokinetic evaluation of BNC105P: a phase I trial of a novel vascular disrupting agent and inhibitor of cancer cell proliferation. Clin Cancer Res. 2011 Aug 1;17(15):5152-60. doi: 10.1158/1078-0432.CCR-11-0937. Epub 2011 Jun 20. PubMed PMID: 21690571.
3: Kremmidiotis G, Leske AF, Lavranos TC, Beaumont D, Gasic J, Hall A, O'Callaghan M, Matthews CA, Flynn B. BNC105: a novel tubulin polymerization inhibitor that selectively disrupts tumor vasculature and displays single-agent antitumor efficacy. Mol Cancer Ther. 2010 Jun;9(6):1562-73. doi: 10.1158/1535-7163.MCT-09-0815. Epub 2010 Jun 1. PubMed PMID: 20515948.
