An inhibitor of TGF-β signaling and TH17 differentiation
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Halofuginone (hydrochloride)

Item No. 13370

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone, monohydrochloride
CAS Number
1217623-74-9
Molecular Formula
C16H17BrClN3O3 • HCl
Formula Weight
451.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleDMSO: solubleWater: solubleWater: Soluble
λmax
242, 274, 314, 327 nm
SMILES
BrC1=C(Cl)C=C2C(N=CN(CC(C[C@H]3NCCC[C@@H]3O)=O)C2=O)=C1.Cl
InChi Code
InChI=1S/C16H17BrClN3O3.ClH/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14;/h5-6,8,14-15,19,23H,1-4,7H2;1H/t14-,15+;/m1./s1
InChi Key
XFFYBQUXAJOKAL-LIOBNPLQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $134

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    1 mg

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    5 mg

    $530

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    Cayman Chemical
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    Product Description

    Halofuginone is a halogenated derivative of febrifugine, a natural quinazolinone-containing compound found in the Chinese herb D. febrifuga.1 It has antimalarial and anticoccidial actions.1 In mammals, halofuginone at 10 ng/ml down-regulates Smad3, blocking TGF-β signaling and preventing both the differentiation of fibroblasts to myofibroblasts and the transitioning of epithelial cells to mesenchymal cells.1,2 Through this action, halofuginone blocks fibrosis and tumor progression in a variety of different models.1,3 This compound also competitively inhibits prolyl-tRNA synthetase (Ki = 18.3 nM), activating the amino acid starvation response.4,5 This prevents the differentiation of TH17 cells, blunting an autoimmune response.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McLaughlin, N.P., Evans, P., and Pines, M. The chemistry and biology of febrifugine and halofuginone. Bioorg. Med. Chem. 22(7), 1993-2004 (2014).

    2. Nelson, E.F., Huang, C.W., Ewel, J.M., et al. Halofuginone down-regulates Smad3 expression and inhibits the TGβ-induced expression of fibrotic markers in human corneal fibroblasts. Mol. Vis. 18, 479-487 (2012).

    3. Pines, M., Snyder, D., Yarkoni, S., et al. Halofuginone to treat fibrosis in chronic graft-versus-host disease and scleroderma. Biol. Blood Marrow Transplant. 9(7), 417-425 (2003).

    4. Keller, T.L., Zocco, D., Sundrud, M.S., et al. Halofuginone and other febrifugine derivatives inhibit prolyl-tRNA synthetase. Nat. Chem. Biol. 8(3), 311-317 (2012).

    5. Sundrud, M.S., Koralov, S.B., Feuerer, M., et al. Halofuginone inhibits TH17 cell differentiation by activating the amino acid starvation response. Science 324(5932), 1334-1338 (2009).