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Halofuginone (hydrobromide) (Standard)

CAT: 0804-HY-N1584AR-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1584AR-01Size:1 mg
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Description
Halofuginone (hydrobromide) (Standard) is the analytical standard of Halofuginone (hydrobromide) . This product is intended for research and analytical applications. Halofuginone (RU-19110) hydrobromid, a Febrifugine derivative, is a competitive prolyl-tRNA synthetase inhibitor with a Ki of 18.3 nM[1][2]. Halofuginone hydrobromid is a specific inhibitor of type-I collagen synthesis and attenuates osteoarthritis (OA) by inhibition of TGF-β activity[3][4]. Halofuginone hydrobromid is also a potent pulmonary vasodilator by activating Kv channels and blocking voltage-gated, receptor-operated and store-operated Ca2+ channels. Halofuginone hydrobromid has anti-malaria, anti-inflammatory, anti-cancer, anti-fibrosis effects[5].
CAS Number
64924-67-0
Product Name Alternative
RU-19110 (hydrobromide) (Standard)
UNSPSC
12352005
Target
Calcium Channel; DNA/RNA Synthesis; Parasite; Reference Standards; Sodium Channel; TGF-beta/Smad
Type
Reference Standards
Related Pathways
Anti-infection; Cell Cycle/DNA Damage; Membrane Transporter/Ion Channel; Neuronal Signaling; Others; Stem Cell/Wnt; TGF-beta/Smad
Field of Research
Cancer; Infection; Inflammation/Immunology; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/halofuginone-hydrobromide-standard.html
Purity
99.80
Smiles
O=C1N(CC(C[C@@H]2NCCC[C@H]2O)=O)C=NC3=C1C=C(Cl)C(Br)=C3.Br
Molecular Formula
C16H18Br2ClN3O3
Molecular Weight
495.59
References & Citations
[1]Tsuchida K, et al. Halofuginone enhances the chemo-sensitivity of cancer cells by suppressing NRF2 accumulation. Free Radic Biol Med. 2017 Feb;103:236-247.|[2]Keller TL, et al. Halofuginone and other Febrifugine derivatives inhibit prolyl-tRNA synthetase. Nat Chem Biol. 2012 Feb 12;8 (3) :311-7.|[3]Cui Z, et al. Halofuginone attenuates osteoarthritis by inhibition of TGF-β activity and H-type vessel formation in subchondral bone. Ann Rheum Dis. 2016 Sep;75 (9) :1714-21.|[4]Tracy L McGaha, et al. Halofuginone, an inhibitor of type-I collagen synthesis and skin sclerosis, blocks transforming-growth-factor-beta-mediated Smad3 activation in fibroblasts. J Invest Dermatol. 2002 Mar;118 (3) :461-70.|[5]Pritesh P Jain, et al. Halofuginone, a Promising Drug for Treatment of Pulmonary Hypertension. Br J Pharmacol. 2021 Mar 10.
Shipping Conditions
Blue Ice
Storage Conditions
4°C, sealed storage, away from light and moisture
Scientific Category
Reference Standards

Chemical Information

Halofuginone Hydrobromide

Halofuginone Hydrobromide is 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.

CAS Number64924-67-0
PubChem CID11591339
IUPAC Name7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one;hydrobromide
Molecular FormulaC16H18Br2ClN3O3
Molecular Weight495.6
Topological Polar Surface Area82
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Heavy Atom Count25
Formal Charge0
Complexity533
SMILES
C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O.Br
InChI
InChI=1S/C16H17BrClN3O3.BrH/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
InChIKey
SJUWEPZBTXEUMU-LIOBNPLQSA-N
Chemical Structure
2D Structure
2D structure of Halofuginone Hydrobromide
CAS: 64924-67-0
CID: 11591339
Formula: C16H18Br2ClN3O3
MW: 495.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight495.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass494.93829
Monoisotopic Mass492.94034
Topological Polar Surface Area82 Ų
Heavy Atom Count25
Formal Charge0
Complexity533
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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