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MedKoo Cat#: 406374 | Name: BMS-566419
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Description:

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

BMS-566419 is a novel chemically synthesized IMPDH inhibitor. The in vitro inhibitory activity of BMS-566419 on IMPDH type I/II, immune cell proliferation and antibody production from lipopolysaccharide (LPS)-stimulated B cells was similar, albeit slightly less potent than that of MPA.

Chemical Structure

BMS-566419
BMS-566419
CAS#566161-24-8

Theoretical Analysis

MedKoo Cat#: 406374

Name: BMS-566419

CAS#: 566161-24-8

Chemical Formula: C28H30FN5O2

Exact Mass: 487.2384

Molecular Weight: 487.57

Elemental Analysis: C, 68.97; H, 6.20; F, 3.90; N, 14.36; O, 6.56

Price and Availability

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10mg USD 550.00 2 Weeks
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Related CAS #
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Synonym
BMS566419; BMS 566419; BMS-566419
IUPAC/Chemical Name
N-(2-(6-(4-ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2-fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide
InChi Key
XEVJUIZOZCFECP-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H30FN5O2/c1-4-33-11-13-34(14-12-33)25-10-9-18(17-30-25)28(2,3)32-27(36)20-16-24-21(15-22(20)29)26(35)19-7-5-6-8-23(19)31-24/h5-10,15-17H,4,11-14H2,1-3H3,(H,31,35)(H,32,36)
SMILES Code
O=C(C(C=C1NC2=C3C=CC=C2)=C(F)C=C1C3=O)NC(C)(C4=CC=C(N5CCN(CC)CC5)N=C4)C
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, 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
More Info
        
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Inosine monophosphatase dehydrogenase (IMPDH) inhibitor.
In vitro activity:
Steady-state enzyme kinetic studies determined that 4m (BMS-566419) was a reversible and uncompetitive inhibitor of IMPDH II with a Ki of 25 ± 3 nM with respect to IMP and 20 ± 4 nM with respect to NAD. Reference: J Med Chem. 2007 Jul 26;50(15):3730-42. https://pubmed.ncbi.nlm.nih.gov/17585753/
In vivo activity:
After 14 days of UUO, interstitial fibrosis was frequently observed in the renal cortex of rats administered vehicle control. BMS-566419 by oral administration showed a significant and dose-dependent suppressive effect on UUO-induced renal fibrosis in histopathological experiments. BMS-566419 treatment also decreased collagen content, as indicated by hydroxyproline concentration, and the expression of collagen type 1 mRNA. BMS-566419 also decreased the expression of mRNA for both MCP-1 and TGF-β1. Reference: Int Immunopharmacol. 2010 Nov;10(11):1434-9. https://pubmed.ncbi.nlm.nih.gov/20832515/
Solvent mg/mL mM comments
Solubility
DMSO 48.8 100.00
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 487.57 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. Watterson SH, Chen P, Zhao Y, Gu HH, Dhar TG, Xiao Z, Ballentine SK, Shen Z, Fleener CA, Rouleau KA, Obermeier M, Yang Z, McIntyre KW, Shuster DJ, Witmer M, Dambach D, Chao S, Mathur A, Chen BC, Barrish JC, Robl JA, Townsend R, Iwanowicz EJ. Acridone-based inhibitors of inosine 5'-monophosphate dehydrogenase: discovery and SAR leading to the identification of N-(2-(6-(4-ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2- fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419). J Med Chem. 2007 Jul 26;50(15):3730-42. doi: 10.1021/jm070299x. Epub 2007 Jun 22. PMID: 17585753. 2. Nakanishi T, Morokata T, Noto T, Kubo K, Umeno H, Kinugasa F, Eikyu Y, Kozuki Y, Seki N. Effect of the inosine 5'-monophosphate dehydrogenase inhibitor BMS-566419 on renal fibrosis in unilateral ureteral obstruction in rats. Int Immunopharmacol. 2010 Nov;10(11):1434-9. doi: 10.1016/j.intimp.2010.08.011. Epub 2010 Sep 9. PMID: 20832515. 3. Nakanishi T, Morokata T, Kubo K, Umeno H, Eikyu Y, Kozuki Y, Seki N. Effect of the inosine 5'-monophosphate dehydrogenase inhibitor BMS-566419 on rat cardiac allograft rejection. Int Immunopharmacol. 2010 Jan;10(1):91-7. doi: 10.1016/j.intimp.2009.09.026. Epub 2009 Oct 18. PMID: 19840872.
In vitro protocol:
1. Watterson SH, Chen P, Zhao Y, Gu HH, Dhar TG, Xiao Z, Ballentine SK, Shen Z, Fleener CA, Rouleau KA, Obermeier M, Yang Z, McIntyre KW, Shuster DJ, Witmer M, Dambach D, Chao S, Mathur A, Chen BC, Barrish JC, Robl JA, Townsend R, Iwanowicz EJ. Acridone-based inhibitors of inosine 5'-monophosphate dehydrogenase: discovery and SAR leading to the identification of N-(2-(6-(4-ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2- fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419). J Med Chem. 2007 Jul 26;50(15):3730-42. doi: 10.1021/jm070299x. Epub 2007 Jun 22. PMID: 17585753.
In vivo protocol:
1. Nakanishi T, Morokata T, Noto T, Kubo K, Umeno H, Kinugasa F, Eikyu Y, Kozuki Y, Seki N. Effect of the inosine 5'-monophosphate dehydrogenase inhibitor BMS-566419 on renal fibrosis in unilateral ureteral obstruction in rats. Int Immunopharmacol. 2010 Nov;10(11):1434-9. doi: 10.1016/j.intimp.2010.08.011. Epub 2010 Sep 9. PMID: 20832515. 2. Nakanishi T, Morokata T, Kubo K, Umeno H, Eikyu Y, Kozuki Y, Seki N. Effect of the inosine 5'-monophosphate dehydrogenase inhibitor BMS-566419 on rat cardiac allograft rejection. Int Immunopharmacol. 2010 Jan;10(1):91-7. doi: 10.1016/j.intimp.2009.09.026. Epub 2009 Oct 18. PMID: 19840872.
1: Nakanishi T, Morokata T, Noto T, Kubo K, Umeno H, Kinugasa F, Eikyu Y, Kozuki Y, Seki N. Effect of the inosine 5'-monophosphate dehydrogenase inhibitor BMS-566419 on renal fibrosis in unilateral ureteral obstruction in rats. Int Immunopharmacol. 2010 Nov;10(11):1434-9. doi: 10.1016/j.intimp.2010.08.011. Epub 2010 Sep 9. PubMed PMID: 20832515. 2: Nakanishi T, Morokata T, Kubo K, Umeno H, Eikyu Y, Kozuki Y, Seki N. Effect of the inosine 5'-monophosphate dehydrogenase inhibitor BMS-566419 on rat cardiac allograft rejection. Int Immunopharmacol. 2010 Jan;10(1):91-7. doi: 10.1016/j.intimp.2009.09.026. Epub 2009 Oct 18. PubMed PMID: 19840872. 3: Watterson SH, Chen P, Zhao Y, Gu HH, Dhar TG, Xiao Z, Ballentine SK, Shen Z, Fleener CA, Rouleau KA, Obermeier M, Yang Z, McIntyre KW, Shuster DJ, Witmer M, Dambach D, Chao S, Mathur A, Chen BC, Barrish JC, Robl JA, Townsend R, Iwanowicz EJ. Acridone-based inhibitors of inosine 5'-monophosphate dehydrogenase: discovery and SAR leading to the identification of N-(2-(6-(4-ethylpiperazin-1-yl)pyridin-3-yl)propan-2-yl)-2- fluoro-9-oxo-9,10-dihydroacridine-3-carboxamide (BMS-566419). J Med Chem. 2007 Jul 26;50(15):3730-42. Epub 2007 Jun 22. PubMed PMID: 17585753.