LFM-A13
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MedKoo CAT#: 401531

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.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 150 2 Weeks
100mg USD 250 2 Weeks
200mg USD 450 2 Weeks
500mg USD 850 2 Weeks
1g USD 1450 2 Weeks
2g USD 1950 2 Weeks
5g USD 3250 2 Weeks
10g USD 4950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-27. Prices are subject to change without notice.

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

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Theoretical Analysis

MedKoo Cat#: 401531
Name: LFM-A13
CAS#: 244240-24-2
Chemical Formula: C11H8Br2N2O2
Exact Mass: 357.89525
Molecular Weight: 360.0
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


Technical Data

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


Additional Information

  
 
 
 


References

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.