64924-67-0 Usage
Description
Halofuginone hydrobromide is the hydrobromide salt of halofuginone, a semisynthetic quinazolinone alkaloid anticoccidial derived from the plant Dichroa febrifuga. It possesses antifibrotic and potential antineoplastic activities, specifically inhibiting collagen type I gene expression and matrix metalloproteinase 2 (MMP-2) gene expression. This inhibition may lead to the suppression of angiogenesis, tumor stromal cell development, and tumor cell growth. Halofuginone hydrobromide is a white to off-white solid.
Uses
Used in Veterinary Medicine:
Halofuginone hydrobromide is used as an antiprotozoal (coccidiostat) for the treatment and prevention of coccidiosis in poultry. It helps in reducing the impact of the disease on the birds' health and productivity.
Used in Pharmaceutical Applications:
Halofuginone hydrobromide is used as an antifibrotic agent for the potential treatment of fibro-proliferative diseases. Its ability to inhibit collagen type I and MMP-2 gene expression can help in reducing the excessive accumulation of extracellular matrix components, which is a characteristic of these diseases.
Used in Anticancer Applications:
Halofuginone hydrobromide is used as a potential antineoplastic agent due to its inhibitory effects on tumor cell growth. By suppressing angiogenesis, tumor stromal cell development, and tumor cell growth, it may contribute to the development of novel cancer therapies.
Used in Drug Delivery Systems:
Halofuginone hydrobromide can be incorporated into drug delivery systems to improve its bioavailability and therapeutic outcomes. These systems can be designed to target specific tissues or cells, enhancing the efficacy of the compound in treating various conditions, including fibrosis and cancer.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 64924-67-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,9,2 and 4 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 64924-67:
(7*6)+(6*4)+(5*9)+(4*2)+(3*4)+(2*6)+(1*7)=150
150 % 10 = 0
So 64924-67-0 is a valid CAS Registry Number.
InChI:InChI=1/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+;/m0./s1
64924-67-0Relevant articles and documents
New synthesis process for preparing veterinary bulk drug halofuginone hydrobromide
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Paragraph 0021; 0027-0031, (2021/10/20)
The invention discloses a process method for preparing veterinary raw material drug halofuginone hydrobromide, and relates to the field of veterinary drugs and the technical field of drug synthesis. According to the invention, a novel process route is adopted, 7-bromo-3-(8-bromo-5-hydroxy-2-oxo-3-octenyl)-6-chloro-4 (3H)-quinazolinone is taken as a starting raw material, and the halofuginone hydrobromide is prepared through three-step reaction of ammonolysis, purification and salification, so that the problems of difficulty in obtaining raw materials, harsh reaction conditions, high cost and the like in the existing synthesis method are solved. The novel synthesis process for preparing the veterinary drug halofuginone hydrobromide is simple in process operation, low in production cost, few in steps, high in total yield, small in pollution and suitable for industrial mass production.
Synthetic method for halofuginone and intermediate of halofuginone
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Paragraph 0277-0279, (2019/11/28)
The invention relates to a synthetic method for halofuginone and an intermediate of the halofuginone. The reaction formula is shown in the description, wherein R1 is one selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and t-butyl; R2 is one selected from the group consisting of methyl and ethyl; and R3 is one selected from the group consisting of methoxyformyl, ethoxyformyl, tert-butoxyformyl, benzyloxyformyl, trichloroethoxyformyl and benzyl. The synthetic method provided by the invention has the advantages of a simple process, low costs, few by-products in the synthetic process, a simple purification process, no need of column chromatography purification, a high product yield, less impurities, high purity, and controllable product quality, easily meets ICH declaration requirements and can be used for industrial production of the halofuginone.
A convergent strategy towards febrifugine and related compounds
Maiden,Mbelesi,Procopiou,Swanson,Harrity
, p. 4159 - 4169 (2018/06/12)
We report a modular five step synthetic route to the febrifugines that employs 2-(chloromethyl)allyl-trimethylsilane as a conjunctive reagent for the coupling of the piperidine and quinazolinone groups. We also demonstrate the application of a recent Rh-catalyzed quinazolinone synthesis for the facile generation of febrifugine analogs.
