Halofuginone

Halofuginone, sold under the brand name Halocur, is a coccidiostat used in veterinary medicine. It is a synthetic halogenated derivative of febrifugine, a natural quinazolinone alkaloid which can be found in the Chinese herb Dichroa febrifuga (Chang Shan).^[3] Collgard Biopharmaceuticals is developing halofuginone for the treatment of scleroderma and it has received orphan drug designation from the U.S. Food and Drug Administration.^[4]

Halofuginone

Clinical data
Trade names	Halocur
AHFS/Drugs.com	International Drug Names
ATCvet code	QP51BX01 (WHO)
Legal status
Legal status	EU: Rx-only[1][2]
Identifiers
IUPAC name 7-Bromo-6-chloro-3-[3-[(2S,3R)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4-quinazolinone
CAS Number	55837-20-2 Y
PubChem CID	400772
ChemSpider	355164 N
UNII	L31MM1385E
ChEMBL	ChEMBL1199540 N
CompTox Dashboard (EPA)	DTXSID0048260
Chemical and physical data
Formula	C16H17BrClN3O3
Molar mass	414.68 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(CN3C=NC2=CC(Br)=C(Cl)C=C2C3=O)C[C@@H]1NCCC[C@H]1O
InChI InChI=1S/C16H17BrClN3O3/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/t14-,15+/m0/s1 N Key:LVASCWIMLIKXLA-LSDHHAIUSA-N N
NY (what is this?)  (verify)

Halofuginone inhibits the development of T helper 17 cells, immune cells that play an important role in autoimmune disease, but it does not affect other kinds of T cells which are involved in normal immune function.^[5] Halofuginone therefore has potential for the treatment of autoimmune disorders.^[5]

Halofuginone is also an inhibitor of collagen type I gene expression and as a consequence it may inhibit tumor cell growth.^[3] Halofuginone exerts its effects by acting as a high affinity inhibitor of the enzyme glutamyl-prolyl tRNA synthetase. Inhibition of prolyl tRNA charging leads to the accumulation of uncharged prolyl tRNAs, which serve as a signal to initiate the amino acid starvation response, which in turn exerts anti-inflammatory and anti-fibrotic effects.^[6]