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HomeProduct name listHalofuginone hydrobromide

Halofuginone hydrobromide

Synonym(s):trans-(±)-7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone monohydrobromide

  • CAS NO.:64924-67-0
  • Empirical Formula: C16H17BrClN3O3.HBr
  • Molecular Weight: 495.59
  • MDL number: MFCD00946455
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
Halofuginone hydrobromide Structural

What is Halofuginone hydrobromide?

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

The Uses of Halofuginone hydrobromide

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).

Properties of Halofuginone hydrobromide

Melting point: 247° (dec)
storage temp.  Store at -20°C
solubility  Soluble to 100 mM in DMSO.
form  Solid
form  neat
color  White to off-white

Safety information for Halofuginone hydrobromide

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Environment
GHS09
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P262:Do not get in eyes, on skin, or on clothing.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Halofuginone hydrobromide

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