WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H401531
CAS#: 244240-24-2
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.
Hodoodo Cat#: H401531
Name: LFM-A13
CAS#: 244240-24-2
Chemical Formula: C11H8Br2N2O2
Exact Mass: 357.90
Molecular Weight: 360.005
Elemental 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
Appearance: Solid powder
Purity: >98%
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: >5 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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 360.01 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.
| 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Uckun F, Dibirdik I, Sarkissian A, Qazi S. In vitro and in vivo chemosensitizing activity of LFM-A13, a dual-function inhibitor of Bruton's tyrosine kinase and polo-like kinases, against human 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, a leflunomide 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 GMP grade 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. Preclinical toxicity and pharmacokinetics of the Bruton's tyrosine kinase-targeting anti-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 of Polo-like kinase (PLK). Bioorg Med Chem. 2007 Jan 15;15(2):800-14. Epub 2006 Oct 26. PubMed PMID: 17098432.
6: Tibbles HE, Samuel P, Erbeck D, Mahajan S, Uckun FM. In vivo toxicity and antithrombotic profile of the oral formulation of the antileukemic agent, 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, Löwenberg B, von Lindern M. The Btk inhibitor LFM-A13 is a potent inhibitor of Jak2 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. The anti-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 and activation of Tec family kinases in human neutrophils. II. Effects of LFM-A13, a specific Btk inhibitor. J Immunol. 2003 May 15;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 pharmacokinetic features, toxicity profile, and chemosensitizing activity of alpha-cyano-beta-hydroxy-beta- methyl-N-(2,5-dibromophenyl)propenamide (LFM-A13), a novel antileukemic agent targeting Bruton's tyrosine kinase. Clin Cancer Res. 2002 May;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 targeting Bruton'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.
