BAY-1816032
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MedKoo CAT#: 408069

CAS#: 1891087-61-8

Description: BAY-1816032 is a potent and oral available BUB1 (budding uninhibited by benzimidazoles 1) kinase inhibitor with an IC50 of 7 nM. BAY 1816032 showed long target residence time and induced chromosome mis-segregation upon combination with low concentrations of paclitaxel. It was synergistic or additive in combination with paclitaxel or docetaxel, as well as with ATR or PARP inhibitors in cellular assays. Tumor xenograft studies demonstrated a strong and statistically significant reduction of tumor size and excellent tolerability upon combination of BAY 1816032 with paclitaxel or olaparib as compared with the respective monotherapies.

Chemical Structure

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BAY-1816032
CAS# 1891087-61-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 408069
Name: BAY-1816032
CAS#: 1891087-61-8
Chemical Formula: C27H24F2N6O4
Exact Mass: 534.18
Molecular Weight: 534.524
Elemental Analysis: C, 60.67; H, 4.53; F, 7.11; N, 15.72; O, 11.97

Price and Availability

Size Price Availability Quantity
50mg USD 650 2 Weeks
100mg USD 1050 2 Weeks
200mg USD 1950 2 Weeks
500mg USD 3450 2 Weeks
1g USD 5450 2 Weeks
2g USD 8450 2 Weeks
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Synonym: BAY-1816032; BAY 1816032; BAY1816032

IUPAC/Chemical Name: 2-(3,5-difluoro-4-((3-(5-methoxy-4-((3-methoxypyridin-4-yl)amino)pyrimidin-2-yl)-1H-indazol-1-yl)methyl)phenoxy)ethan-1-ol

InChi Key: QVOGVAVHOLLLAZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H24F2N6O4/c1-37-23-13-30-8-7-21(23)32-26-24(38-2)14-31-27(33-26)25-17-5-3-4-6-22(17)35(34-25)15-18-19(28)11-16(12-20(18)29)39-10-9-36/h3-8,11-14,36H,9-10,15H2,1-2H3,(H,30,31,32,33)

SMILES Code: COC1=C(NC2=NC(C3=NN(CC4=C(F)C=C(OCCO)C=C4F)C5=C3C=CC=C5)=NC=C2OC)C=CN=C1

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

Shelf Life: >3 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:

Product Data:
Product Data
Instruction:
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Biological target: BAY-1816032 is a BUB1 (budding uninhibited by benzimidazoles 1) kinase inhibitor with an IC50 of 7 nM.
In vitro activity: BAY 1816032 abrogated histone H2A-Thr120 phosphorylation, the best validated substrate of BUB1 kinase, in nocodazole-arrested HeLa cells after 1 hour of compound incubation with an IC50 of 29 ± 23 nmol/L demonstrating its potent intracellular inhibition of BUB1 kinase activity. However, the functionality of the spindle assembly checkpoint was not affected by BUB1 kinase inhibition as indicated by persistent histone H3-Ser10 phosphorylation in nocodazole-arrested HeLa cells upon 4-hour incubation at concentrations up to 10 μmol/L. Reference: Clin Cancer Res. 2019 Feb 15;25(4):1404-1414. https://clincancerres.aacrjournals.org/content/25/4/1404.long
In vivo activity: The combination of BAY 1816032 with paclitaxel was evaluated in the SUM-149 model of triple-negative breast cancer. Treatment of tumor-bearing female nude mice with BAY 1816032 as single agent did not show any significant effect on the growth of SUM-149 tumors (Fig. 3A). Paclitaxel initially suppressed tumor growth; however, starting around day 28, tumors gained size and grew out although the dose of paclitaxel had been increased from 8 mg/kg to the MTD of 20 mg/kg from day 24 onward. In contrast, the tumors from the BAY 1816032 plus paclitaxel combination treatment group grew much slower and entered a phase of stable disease around day 46. An analysis of the median tumor areas of the paclitaxel single-agent group and the combination group at day 54 showed a statistically significant difference between the two treatment groups (P < 0.05, ANOVA on ranks). Reference: Clin Cancer Res. 2019 Feb 15;25(4):1404-1414. https://clincancerres.aacrjournals.org/content/25/4/1404.long

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.5 70.16

Preparing Stock Solutions

The following data is based on the product molecular weight 534.52 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
Formulation protocol: 1. Siemeister G, Mengel A, Fernández-Montalván AE, Bone W, Schröder J, Zitzmann-Kolbe S, Briem H, Prechtl S, Holton SJ, Mönning U, von Ahsen O, Johanssen S, Cleve A, Pütter V, Hitchcock M, von Nussbaum F, Brands M, Ziegelbauer K, Mumberg D. Inhibition of BUB1 Kinase by BAY 1816032 Sensitizes Tumor Cells toward Taxanes, ATR, and PARP Inhibitors In Vitro and In Vivo. Clin Cancer Res. 2019 Feb 15;25(4):1404-1414. doi: 10.1158/1078-0432.CCR-18-0628. Epub 2018 Nov 14. PMID: 30429199.
In vitro protocol: 1. Siemeister G, Mengel A, Fernández-Montalván AE, Bone W, Schröder J, Zitzmann-Kolbe S, Briem H, Prechtl S, Holton SJ, Mönning U, von Ahsen O, Johanssen S, Cleve A, Pütter V, Hitchcock M, von Nussbaum F, Brands M, Ziegelbauer K, Mumberg D. Inhibition of BUB1 Kinase by BAY 1816032 Sensitizes Tumor Cells toward Taxanes, ATR, and PARP Inhibitors In Vitro and In Vivo. Clin Cancer Res. 2019 Feb 15;25(4):1404-1414. doi: 10.1158/1078-0432.CCR-18-0628. Epub 2018 Nov 14. PMID: 30429199.
In vivo protocol: 1. Siemeister G, Mengel A, Fernández-Montalván AE, Bone W, Schröder J, Zitzmann-Kolbe S, Briem H, Prechtl S, Holton SJ, Mönning U, von Ahsen O, Johanssen S, Cleve A, Pütter V, Hitchcock M, von Nussbaum F, Brands M, Ziegelbauer K, Mumberg D. Inhibition of BUB1 Kinase by BAY 1816032 Sensitizes Tumor Cells toward Taxanes, ATR, and PARP Inhibitors In Vitro and In Vivo. Clin Cancer Res. 2019 Feb 15;25(4):1404-1414. doi: 10.1158/1078-0432.CCR-18-0628. Epub 2018 Nov 14. PMID: 30429199.

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Siemeister G, Mengel A, Fernández-Montalván AE, et al. Inhibition of BUB1 Kinase by BAY 1816032 Sensitizes Tumor Cells toward Taxanes, ATR, and PARP Inhibitors In Vitro and In Vivo. Clin Cancer Res. 2019;25(4):1404–1414. doi:10.1158/1078-0432.CCR-18-0628