Halofuginone (hydrobromide) (Standard)

CAT: 0804-HY-N1584AR-01Size: 1 mgDry Ice: NoHazardous: No

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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 Number	64924-67-0
PubChem CID	11591339
IUPAC Name	7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one;hydrobromide
Molecular Formula	C16H18Br2ClN3O3
Molecular Weight	495.6
Topological Polar Surface Area	82
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Heavy Atom Count	25
Formal Charge	0
Complexity	533

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

CAS: 64924-67-0

CID: 11591339

Formula: C16H18Br2ClN3O3

MW: 495.6

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	495.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	494.93829
Monoisotopic Mass	492.94034
Topological Polar Surface Area	82 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	533
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

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TBW01506	Halofuginone Hydrobromide
1993/50	Halofuginone hydrobromide 50 mg
TBW01342	Halofuginone

Halofuginone (hydrobromide) (Standard)

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