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Halofuginone

Halofuginone structure

CAS No:
55837-20-2
Formula:
C16H17BrClN3O3
Chemical Name:
Halofuginone
Synonyms:
4(3H)-Quinazolinone,7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-,rel-;4(3H)-Quinazolinone,7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-,trans-(±)-;rel-7-Bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone;Halofuginone;4(3H)-Quinazolinone,7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-,trans-;Tempostatin;Kriptazen
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Halofuginone (RU-19110) is a less-toxic form of Febrifugine, which is isolated from the plant Dichroa febrifuga[1]. Halofuginone inhibits prolyl-tRNA synthetase in an ATP-dependent manner with a Ki of 18.3 nM[2]. Halofuginone attenuates osteoarthritis (OA) by inhibition of TGF-β activity[3].

Halofuginone Basic Attributes

Molecular Weight：

414.68

Exact Mass：

414.68

EC Number：

1806241-263-5

DSSTox ID：

DTXSID0048260

ATC Code：

QP51AX08

Characteristics

PSA：

84.22000

XLogP3：

2.21330

Appearance：

off-white solid

Density：

1.7±0.1 g/cm3

Melting Point：

192-195 °C

Boiling Point：

595.8±60.0°C at 760 mmHg

Flash Point：

314.1±32.9 °C

Refractive Index：

1.712

Storage Conditions：

-20°C

Safety Information

GHS Classification：

Not Classified

Drug Information

Drug Indication：

In newborn calves:Prevention of diarrhoea due to diagnosed Cryptosporidium parvum infection, in farms with history of cryptosporidiosis. Administration should start in the first 24 to 48 hours of age.Reduction of diarrhoea due to diagnosed Cryptosporidium parvum infection. Administration should start within 24 hours after the onset of diarrhoea. In both cases, the reduction of oocysts excretion has been demonstrated.|In newborn calvesPrevention of diarrhoea due to diagnosed Cryptosporidium parvum in farms with history of cryptosporidiosis.Administration should start in the first 24 to 48 hours of age.Reduction of diarrhoea due to diagnosed Cryptosporidium parvum.Administration should start within 24 hours after the onset of diarrhoea.In both cases, the reduction of oocyst excretion has been demonstrated.|In new born calves:- Prevention of diarrhoea due to diagnosed Cryptosporidium parvum, in farms with history of cryptosporidiosis,Administration should start in the first 24 to 48 hours of age- Reduction of diarrhoea due to diagnosed Cryptosporidium parvum.Administration should start within 24 hours after the onset of diarrhoea.In both cases, the reduction of oocysts excretion has been demonstrated.

MeSH：

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)|Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

MeSH Entry Terms：

7-bromo-6-chlorofebrifugine

Halofuginone Use and Manufacturing

Methods of Manufacturing

The alkaloid extracted from the Chinese herbal medicine Changshan is then chemically synthesized. Using 3-bromo-4-chloro-6-carboxyaniline as the raw material, and then refluxing with dimethylformamide and formamide for 16h, 7-bromo-6-chloro-4-3H-quinazolinone was synthesized. It is then condensed with 3-methoxy-2-(γ-bromoacetone)piperidine in hydrogen bromide solution. The intermediate 3-methoxy-2-(γ-bromoacetone) piperidine can be obtained from 3-methoxy-2-acetone piperidine by bromination at room temperature:

Uses

Halogenated derivative of febrigugine. Used as an antiprotozoal

Use Classification：

Veterinary drugs -> Halagon -> EMA Drug Category|halofuginone, Other antiprotozoal agents -> Veterinary pharmacotherapeutic group|Veterinary drugs -> Halocur -> EMA Drug Category|Antiprotozoals -> Veterinary pharmacotherapeutic group|Veterinary drugs -> Kriptazen -> EMA Drug Category

Computed Properties

Molecular Weight:414.7
XLogP3:1.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:413.01418
Monoisotopic Mass:413.01418
Topological Polar Surface Area:82
Heavy Atom Count:24
Complexity:533
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Dimethylformamide

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