BMS582949 free base
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MedKoo CAT#: 555138

CAS#: 623152-17-0 (free base)

Description: BMS-582949 is a potent and selective P38 mitogen-activated protein kinase (P38 MAPK) inhibitor. BMS-582949 is currently under Phase II clinical trials for the treatment of inflammatory diseases. One clinical study showed that, in stable atherosclerosis, 12 weeks of treatment with BMS-582949 did not reduce arterial inflammation or hs-CRP compared to placebo, whereas intensification of statin therapy significantly decreased arterial inflammation. p38α MAP kinase plays a crucial role in regulating the biosynthesis of many inflammatory cytokines including TNFα and IL-1β.


Price and Availability

Size
Price

10mg
USD 90
100mg
USD 450
1g
USD 2450
Size
Price

25mg
USD 150
200mg
USD 750
2g
USD 3950
Size
Price

50mg
USD 250
500mg
USD 1450
5g
USD 6850

BMS582949 free base, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 200mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 555138
Name: BMS582949 free base
CAS#: 623152-17-0 (free base)
Chemical Formula: C22H26N6O2
Exact Mass: 406.2117
Molecular Weight: 406.49
Elemental Analysis: C, 65.01; H, 6.45; N, 20.68; O, 7.87


Related CAS #: 623152-17-0 (free base)   912806-16-7 (HCl)    

Synonym: BMS582949 free base; BMS-582949; BMS 582949; BMS582949; PS-540446; PS 540446; PS540446.

IUPAC/Chemical Name: 4-((5-(cyclopropylcarbamoyl)-2-methylphenyl)amino)-5-methyl-N-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

InChi Key: GDTQLZHHDRRBEB-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H26N6O2/c1-4-9-23-22(30)17-11-28-19(14(17)3)20(24-12-25-28)27-18-10-15(6-5-13(18)2)21(29)26-16-7-8-16/h5-6,10-12,16H,4,7-9H2,1-3H3,(H,23,30)(H,26,29)(H,24,25,27)

SMILES Code: O=C(C1=CN2N=CN=C(NC3=CC(C(NC4CC4)=O)=CC=C3C)C2=C1C)NCCC


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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:
>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).

Harmonized System Code:
293490


References

1: Liu C, Lin J, Hynes J, Wu H, Wrobleski ST, Lin S, Dhar TG, Vrudhula VM, Sun JH, Chao S, Zhao R, Wang B, Chen BC, Everlof G, Gesenberg C, Zhang H, Marathe PH, McIntyre KW, Taylor TL, Gillooly K, Shuster DJ, McKinnon M, Dodd JH, Barrish JC, Schieven GL, Leftheris K. Discovery of ((4-(5-(Cyclopropylcarbamoyl)-2-methylphenylamino)-5-methylpyrrolo[1,2-f][1,2,4]t riazine-6-carbonyl)(propyl)carbamoyloxy)methyl-2-(4-(phosphonooxy)phenyl)acetate (BMS-751324), a Clinical Prodrug of p38α MAP Kinase Inhibitor. J Med Chem. 2015 Sep 22. [Epub ahead of print] PubMed PMID: 26359680.

2: Saxena A, Shah D, Padmanabhan S, Gautam SS, Chowan GS, Mandlekar S, Desikan S. Prediction of pH dependent absorption using in vitro, in silico, and in vivo rat models: Early liability assessment during lead optimization. Eur J Pharm Sci. 2015 Aug 30;76:173-80. doi: 10.1016/j.ejps.2015.05.006. Epub 2015 May 8. PubMed PMID: 25960252.

3: Emami H, Vucic E, Subramanian S, Abdelbaky A, Fayad ZA, Du S, Roth E, Ballantyne CM, Mohler ER, Farkouh ME, Kim J, Farmer M, Li L, Ehlgen A, Langenickel TH, Velasquez L, Hayes W, Tawakol A. The effect of BMS-582949, a P38 mitogen-activated protein kinase (P38 MAPK) inhibitor on arterial inflammation: a multicenter FDG-PET trial. Atherosclerosis. 2015 Jun;240(2):490-6. doi: 10.1016/j.atherosclerosis.2015.03.039. Epub 2015 Mar 28. PubMed PMID: 25913664.

4: Liu C, Lin J, Everlof G, Gesenberg C, Zhang H, Marathe PH, Malley M, Galella MA, McKinnon M, Dodd JH, Barrish JC, Schieven GL, Leftheris K. Synthesis and evaluation of carbamoylmethylene linked prodrugs of BMS-582949, a clinical p38α inhibitor. Bioorg Med Chem Lett. 2013 May 15;23(10):3028-33. doi: 10.1016/j.bmcl.2013.03.022. Epub 2013 Mar 15. PubMed PMID: 23578688.

5: Freebern WJ, Bigwarfe TJ, Price KD, Haggerty HG. Methods: implementation of in vitro and ex vivo phagocytosis and respiratory burst function assessments in safety testing. J Immunotoxicol. 2013 Jan-Mar;10(1):106-17. doi: 10.3109/1547691X.2012.736427. Epub 2012 Nov 23. PubMed PMID: 23173903.

6: Liu C, Lin J, Wrobleski ST, Lin S, Hynes J, Wu H, Dyckman AJ, Li T, Wityak J, Gillooly KM, Pitt S, Shen DR, Zhang RF, McIntyre KW, Salter-Cid L, Shuster DJ, Zhang H, Marathe PH, Doweyko AM, Sack JS, Kiefer SE, Kish KF, Newitt JA, McKinnon M, Dodd JH, Barrish JC, Schieven GL, Leftheris K. Discovery of 4-(5-(cyclopropylcarbamoyl)-2-methylphenylamino)-5-methyl-N-propylpyrrolo[1,2-f][ 1,2,4]triazine-6-carboxamide (BMS-582949), a clinical p38α MAP kinase inhibitor for the treatment of inflammatory diseases. J Med Chem. 2010 Sep 23;53(18):6629-39. doi: 10.1021/jm100540x. PubMed PMID: 20804198.

7: Norman P. BMS-582949: crystalline form of a p38alpha inhibitor? WO2008079857. Expert Opin Ther Pat. 2009 Aug;19(8):1165-8. doi: 10.1517/13543770902816160. PubMed PMID: 19505194.