LFM-A13

new

featured

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

Description:LFM-A13 is a potent and selective inhibitor of Bruton's tyrosine kinase (BTK). LFM-A13 may be useful as a new class of chemosensitizing and apoptosis-promoting antileukemic agents for treatment of patients with chemotherapy-resistant B-lineage leukemias or lymphomas.

Price and Availability

LFM-A13, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 401531Name: LFM-A13CAS#: 244240-24-2Chemical Formula: C11H8Br2N2O2Exact Mass: 357.89525Molecular Weight: 360.0Elemental Analysis: C, 36.70; H, 2.24; Br, 44.39; N, 7.78; O, 8.89

Synonym:LFM A13; LFM-A13; LFM A13

IUPAC/Chemical Name:2-Cyano-N-(2,5-dibromophenyl)-3-hydroxy-2-butenamide

InChi Key:UVSVTDVJQAJIFG-VURMDHGXSA-N

InChi Code:InChI=1S/C11H8Br2N2O2/c1-6(16)8(5-14)11(17)15-10-4-7(12)2-3-9(10)13/h2-4,16H,1H3,(H,15,17)/b8-6-

SMILES Code:C/C(O)=C(C#N)/C(NC1=CC(Br)=CC=C1Br)=O

Technical Data

Additional Information

References

1: Uckun F, Dibirdik I, Sarkissian A, Qazi S. Invitro and in vivo chemosensitizing activity of LFM-A13, a dual-functioninhibitor of Bruton"s tyrosine kinase and polo-like kinases, againsthuman leukemic B-cell precursors. Arzneimittelforschung.2011;61(4):252-9. doi: 10.1055/s-0031-1296196. PubMed PMID: 21650085.

2: Uckun FM. Chemosensitizing anti-cancer activity of LFM-A13, aleflunomide metabolite analog targeting polo-like kinases. Cell Cycle.2007 Dec 15;6(24):3021-6. Epub 2007 Sep 26. PubMed PMID: 18073537.

3: DuMez D, Venkatachalam TK, Uckun FM. Large-scale synthesis of GMPgrade alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl)propenamide (LFM-A13), a new anti-cancer drug candidate.Arzneimittelforschung. 2007;57(3):155-63. PubMed PMID: 17469650.

4: Uckun FM, Tibbles H, Venkatachalam T, DuMez D, Erbeck D. Preclinicaltoxicity and pharmacokinetics of the Bruton"s tyrosine kinase-targetinganti-leukemic drug candidate, alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl) propenamide (LFM-A13). Arzneimittelforschung.2007;57(1):31-46. PubMed PMID: 17341007.

5: Uckun FM, Dibirdik I, Qazi S, Vassilev A, Ma H, Mao C, Benyumov A,Emami KH. Anti-breast cancer activity of LFM-A13, a potent inhibitor ofPolo-like kinase (PLK). Bioorg Med Chem. 2007 Jan 15;15(2):800-14. Epub2006 Oct 26. PubMed PMID: 17098432.

6: Tibbles HE, Samuel P, Erbeck D, Mahajan S, Uckun FM. In vivo toxicityand antithrombotic profile of the oral formulation of the antileukemicagent, LFM-A13-F. Arzneimittelforschung. 2004;54(6):330-9. PubMed PMID:15281619.

7: van den Akker E, van Dijk TB, Schmidt U, Felida L, Beug H, LöwenbergB, von Lindern M. The Btk inhibitor LFM-A13 is a potent inhibitor ofJak2 kinase activity. Biol Chem. 2004 May;385(5):409-13. PubMed PMID:15196000.

8: Uckun FM, Vassilev A, Bartell S, Zheng Y, Mahajan S, Tibbles HE. Theanti-leukemic Bruton"s tyrosine kinase inhibitor alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl)propenamide (LFM-A13) prevents fatal thromboembolism. Leuk Lymphoma.2003 Sep;44(9):1569-77. PubMed PMID: 14565661.

9: Gilbert C, Levasseur S, Desaulniers P, Dusseault AA, Thibault N,Bourgoin SG, Naccache PH. Chemotactic factor-induced recruitment andactivation of Tec family kinases in human neutrophils. II. Effects ofLFM-A13, a specific Btk inhibitor. J Immunol. 2003 May15;170(10):5235-43. PubMed PMID: 12734372.

10: Uckun FM, Zheng Y, Cetkovic-Cvrlje M, Vassilev A, Lisowski E,Waurzyniak B, Chen H, Carpenter R, Chen CL. In vivo pharmacokineticfeatures, toxicity profile, and chemosensitizing activity of alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl)propenamide (LFM-A13), a novel antileukemicagent targeting Bruton"s tyrosine kinase. Clin Cancer Res. 2002May;8(5):1224-33. PubMed PMID: 12006542.

11: Mahajan S, Ghosh S, Sudbeck EA, Zheng Y, Downs S, Hupke M, Uckun FM.Rational design and synthesis of a novel anti-leukemic agent targetingBruton"s tyrosine kinase (BTK), LFM-A13 [alpha-cyano-beta-hydroxy-beta-methyl-N-(2,5-dibromophenyl)propenamide]. J Biol Chem. 1999 Apr 2;274(14):9587-99.PubMed PMID: 10092645.