| Identification | Back Directory | [Name]
Halofuginone hydrobromide | [CAS]
64924-67-0 | [Synonyms]
Ru-19110
STENOROL
Tempostatin
RU-19110(HBr)
Unii-ptc2969mv1
55837-20-2 (free)
RU-19110 (hydrobromide)
HALOFUGINONEHYDROBROMIDE
Trans-halofuginone hydrobromide
Halofuginone Hydrobromide 64924-67-0
HALOFUGINONE HBR ((2R,3S) AND (2S,3R) MIXTURE)
7-Bromo-6-chloro-3-[3-[(2S,3R)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one hydrobromide
7-BroMo-6-chloro-3-(3-((2S,3R)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one hydrobroMide
(2R*,3S*)-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4-3H-quinazolinone hydrobromide
(+/-)-trans-7-Bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3H)-quinazolinone monohydrobromide
rel-7-BroMo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone HydrobroMide
4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, hydrobromide, trans-(+-)-
4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, hydrobromide, trans-(+/-)-
trans-(+/-)-7-BroMo-6-chloro-3-[3-(3-hydroxy-2-
piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone MonohydrobroMide
4(3H)-Quinazolinone, 7-bromo-6-chloro-3-(3-(2R,3S)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, monohydrobromide, rel-
4(3H)-Quinazolinone,7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-,hydrobromide (1:1), rel- | [Molecular Formula]
C16H17BrClN3O3.HBr | [MDL Number]
MFCD23843776 | [MOL File]
64924-67-0.mol | [Molecular Weight]
495.59 |
| Chemical Properties | Back Directory | [Melting point ]
247° (dec) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble to 100 mM in DMSO. | [form ]
neat | [color ]
White to off-white |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [RIDADR ]
UN2811 - class 6.1 - PG 1 - EHS - Toxic solids, organic, n.o.s., HI: all | [WGK Germany ]
3 | [RTECS ]
VA2397066 |
| Hazard Information | Back Directory | [Description]
Halofuginone hydrobromide (Halofuginone) is a specific collagen Type I inhibitor that antagonize or inhibit the development of new blood vessels, hence can prevent intimal hyperplasia at a vascular anastomosis. It is used in the treatment or prevention of coccidiosis in both humans and animals. | [Chemical Properties]
White to Off-White Solid | [Uses]
Halogenated derivative of Febrifugine. Halofuginone hydrobromide is used as an antiprotozoal (coccidiostat).
| [Definition]
The hydrobromide salt of halofuginone, a semisynthetic quinazolinone alkaloid anticoccidial derived from the plant Dichroa febrifuga, with antifibrotic and potential antineoplastic activities. Halofuginone specifically inhibits collagen type I gene expression and matrix metalloproteinase 2 (MMP-2) gene expression, which may result in the suppression of angiogenesis, tumor stromal cell development, and tumor cell growth. These effects appear to be due to halofuginone-mediated inhibition of the collagen type I and MMP-2 promoters. Collagen type I and MMP-2 play important roles in fibro-proliferative diseases. | [Biological Activity]
Halofuginone hydrobromide is a high affinity competitive prolyl-tRNA synthetase inhibitor (Ki = 18.3 nM). Blocks expression of MMP2. Inhibits ECM invasion in vitro and lung metastasis by bladder cancer cells in mice. Inhibits the development of Th17-driven autoimmunity in a mouse model of multiple sclerosis by activating the amino acid response (AAR) pathway. Also antiparasitic. | [Toxicology]
Halofuginone HBr (Halofuginone hydrobromide) is toxic by inhalation, dermal and ocular routes and is very irritant to both the eye and the skin. It is considered also a skin sensitiser[1].
| [storage]
Store at -20°C | [Mode of action]
Halofuginone is an an ATP-dependent inhibitor prolyl-tRNA synthetase (Ki of 18.3 nM). Halofuginone attenuates osteoarthritis (OA) by inhibition of TGF-β activity. Blocks expression of MMP2 and inhibits ECM invasion in vitro and lung metastasis by bladder cancer cells in mice. Also inhibits the development of Th17-driven autoimmunity in a mouse model of multiple sclerosis by activating the amino acid response (AAR) pathway. | [References]
[1] Vasileios Bampidis, Giovanna Azimonti, Maria de Lourdes Bastos, et al. “Safety of a feed additive consisting of halofuginone hydrobromide (STENOROL?) for chickens for fattening and turkeys (Huvepharma N.V.).” EFSA Journal 20 12 (2022).
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| Questions And Answer | Back Directory | [regulation]
Halofuginone hydrobromide is included in the European Union Register of Feed Additives pursuant to Regulation (EC) No 1831/2003 and is authorized for use in chickens for fattening and turkeys (maximum age 12 weeks) at a dose range of 2–3 mg/kg complete feedingstuffs with a withdrawal time of 5 days[1].
The European Food Safety Authority (EFSA) issued an opinion on the coccidiostat STENOROL? containing 0.6% halofuginone hydrobromide for chickens for fattening and turkeys (EFSA, 2003).
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