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MedKoo Cat#: 573452 | Name: BAY 61-3606 HCl
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Description:

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

BAY 61-3606 HCl is a cell-permeable, reversible inhibitor of spleen tyrosine kinase. BAY 61-3606 HCl can inhibit degranulation and block cytokine release from mast cells. Oral administration of BAY 61-3606 to rats was shown to suppress antigen-induced passive cutaneous anaphylactic reaction, bronchoconstriction, and bronchial edema. It can also sensitize MCF-7 breast cancer cells to TNF-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis by inhibiting Cdk9. This compound has been used in a pre-clinical model to explore the feasibility of targeting Syk in the treatment of retinoblastoma.

Chemical Structure

BAY 61-3606 HCl
BAY 61-3606 HCl
CAS#1615197-10-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 573452

Name: BAY 61-3606 HCl

CAS#: 1615197-10-8 (HCl)

Chemical Formula: C20H19ClN6O3

Exact Mass: 426.1207

Molecular Weight: 426.86

Elemental Analysis: C, 56.28; H, 4.49; Cl, 8.30; N, 19.69; O, 11.24

Price and Availability

Size Price Availability Quantity
5mg USD 385.00 2 Weeks
10mg USD 700.00 2 Weeks
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Related CAS #
732983-37-8 (free base) 1615197-10-8 (HCl)
Synonym
BAY 61-3606 HCl
IUPAC/Chemical Name
2-[[7-(3,4-dimethoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]amino]-3-pyridinecarboxamide, monohydrochloride
InChi Key
HLYFDKZWVIBYKL-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H18N6O3.ClH/c1-28-15-6-5-12(10-16(15)29-2)14-11-17-22-8-9-26(17)20(24-14)25-19-13(18(21)27)4-3-7-23-19;/h3-11H,1-2H3,(H2,21,27)(H,23,24,25);1H
SMILES Code
O=C(C1=CC=CN=C1NC2=NC(C3=CC=C(OC)C(OC)=C3)=CC4=NC=CN24)N.[H]Cl
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
View handling instruction
Biological target:
BAY 61-3606 HCl is an inhibitor of spleen tyrosine kinase with an IC50 of 10 nM.
In vitro activity:
Spleen tyrosine kinase (Syk) inhibitor Bay 61-3606 was identified as a TRAIL sensitizer. Amplification of TRAIL-induced apoptosis by Bay 61-3606 was accompanied by the strong activation of Bak, caspases, and DNA fragmentation. In mechanism of action, Bay 61-3606 sensitized cells to TRAIL via two mechanisms regulating myeloid cell leukemia sequence-1 (Mcl-1). First, Bay 61-3606 triggered ubiquitin-dependent degradation of Mcl-1 by regulating Mcl-1 phosphorylation. Second, Bay 61-3606 downregulated Mcl-1 expression at the transcription level. In this context, Bay 61-3606 acted as an inhibitor of Cyclin-Dependent Kinase (CDK) 9 rather than Syk. Reference: PLoS One. 2015 Dec 31;10(12):e0146073. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4697837/
In vivo activity:
Oral administration of BAY 61-3606 to rats significantly suppressed antigen-induced passive cutaneous anaphylactic reaction, bronchoconstriction, and bronchial edema at 3 mg/kg. Furthermore, BAY 61-3606 attenuated antigen-induced airway inflammation in rats. Reference: J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. https://jpet.aspetjournals.org/content/306/3/1174.long
Solvent mg/mL mM
Solubility
DMF 1.0 2.34
DMSO 30.0 70.28
DMSO:PBS (pH 7.2) (1:30) 0.0 0.07
Ethanol 0.1 0.23
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 426.86 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. Kim SY, Park SE, Shim SM, Park S, Kim KK, Jeong SY, Choi EK, Hwang JJ, Jin DH, Chung CD, Kim I. Bay 61-3606 Sensitizes TRAIL-Induced Apoptosis by Downregulating Mcl-1 in Breast Cancer Cells. PLoS One. 2015 Dec 31;10(12):e0146073. doi: 10.1371/journal.pone.0146073. PMID: 26720004; PMCID: PMC4697837. 2. Du J, Wang Y, Chen D, Ji G, Ma Q, Liao S, Zheng Y, Zhang J, Hou Y. BAY61-3606 potentiates the anti-tumor effects of TRAIL against colon cancer through up-regulating DR4 and down-regulating NF-κB. Cancer Lett. 2016 Dec 28;383(2):145-153. doi: 10.1016/j.canlet.2016.10.002. Epub 2016 Oct 6. PMID: 27721019. 3. Yamamoto N, Takeshita K, Shichijo M, Kokubo T, Sato M, Nakashima K, Ishimori M, Nagai H, Li YF, Yura T, Bacon KB. The orally available spleen tyrosine kinase inhibitor 2-[7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]nicotinamide dihydrochloride (BAY 61-3606) blocks antigen-induced airway inflammation in rodents. J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. doi: 10.1124/jpet.103.052316. Epub 2003 May 23. PMID: 12766258.
In vitro protocol:
1. Kim SY, Park SE, Shim SM, Park S, Kim KK, Jeong SY, Choi EK, Hwang JJ, Jin DH, Chung CD, Kim I. Bay 61-3606 Sensitizes TRAIL-Induced Apoptosis by Downregulating Mcl-1 in Breast Cancer Cells. PLoS One. 2015 Dec 31;10(12):e0146073. doi: 10.1371/journal.pone.0146073. PMID: 26720004; PMCID: PMC4697837. 2. Du J, Wang Y, Chen D, Ji G, Ma Q, Liao S, Zheng Y, Zhang J, Hou Y. BAY61-3606 potentiates the anti-tumor effects of TRAIL against colon cancer through up-regulating DR4 and down-regulating NF-κB. Cancer Lett. 2016 Dec 28;383(2):145-153. doi: 10.1016/j.canlet.2016.10.002. Epub 2016 Oct 6. PMID: 27721019.
In vivo protocol:
1. Yamamoto N, Takeshita K, Shichijo M, Kokubo T, Sato M, Nakashima K, Ishimori M, Nagai H, Li YF, Yura T, Bacon KB. The orally available spleen tyrosine kinase inhibitor 2-[7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]nicotinamide dihydrochloride (BAY 61-3606) blocks antigen-induced airway inflammation in rodents. J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. doi: 10.1124/jpet.103.052316. Epub 2003 May 23. PMID: 12766258. 2. Du J, Wang Y, Chen D, Ji G, Ma Q, Liao S, Zheng Y, Zhang J, Hou Y. BAY61-3606 potentiates the anti-tumor effects of TRAIL against colon cancer through up-regulating DR4 and down-regulating NF-κB. Cancer Lett. 2016 Dec 28;383(2):145-153. doi: 10.1016/j.canlet.2016.10.002. Epub 2016 Oct 6. PMID: 27721019.
1: Unsal D, Kacan M, Temiz-Resitoglu M, Guden DS, Korkmaz B, Sari AN, Buharalioglu CK, Yildirim-Yaroglu H, Tamer-Gumus L, Tunctan B, Malik KU, Sahan-Firat S. The role of Syk/IĸB-α/NF-ĸB pathway activation in the reversal effect of BAY 61-3606, a selective Syk inhibitor, on hypotension and inflammation in a rat model of zymosan-induced non-septic shock. Clin Exp Pharmacol Physiol. 2018 Feb;45(2):155-165. doi: 10.1111/1440-1681.12864. Epub 2017 Nov 28. PubMed PMID: 28949404. 2: Kim SY, Park SE, Shim SM, Park S, Kim KK, Jeong SY, Choi EK, Hwang JJ, Jin DH, Chung CD, Kim I. Bay 61-3606 Sensitizes TRAIL-Induced Apoptosis by Downregulating Mcl-1 in Breast Cancer Cells. PLoS One. 2015 Dec 31;10(12):e0146073. doi: 10.1371/journal.pone.0146073. eCollection 2015. PubMed PMID: 26720004; PubMed Central PMCID: PMC4697837. 3: Mitra R, Bhagavatula ID, Gope R. BAY 61-3606, CDKi, and sodium butyrate treatments alter gene expression in human vestibular schwannomas and cause cell death in vitro. Ecancermedicalscience. 2012;6:285. doi: 10.3332/ecancer.2012.285. Epub 2012 Dec 20. PubMed PMID: 23304241; PubMed Central PMCID: PMC3530378. 4: Yamamoto N, Takeshita K, Shichijo M, Kokubo T, Sato M, Nakashima K, Ishimori M, Nagai H, Li YF, Yura T, Bacon KB. The orally available spleen tyrosine kinase inhibitor 2-[7-(3,4-dimethoxyphenyl)-imidazo[1,2-c]pyrimidin-5-ylamino]nicotinamide dihydrochloride (BAY 61-3606) blocks antigen-induced airway inflammation in rodents. J Pharmacol Exp Ther. 2003 Sep;306(3):1174-81. Epub 2003 May 23. PubMed PMID: 12766258.