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Halofantrine

Halofantrine structure

CAS No:
69756-53-2
Formula:
C26H30Cl2F3NO
Chemical Name:
Halofantrine
Synonyms:
9-Phenanthrenemethanol,1,3-dichloro-α-[2-(dibutylamino)ethyl]-6-(trifluoromethyl)-;1,3-Dichloro-α-[2-(dibutylamino)ethyl]-6-(trifluoromethyl)-9-phenanthrenemethanol;Halofantrine;Halfan;dl-WR 171669;(±)-Halofantrine;66051-63-6
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Solid

3-(dibutylamino)-1-[1,3-dichloro-6-(trifluoromethyl)-9-phenanthrenyl]-1-propanol is a member of phenanthrenes.|Halofantrine is an antimalarial. It belongs to the phenanthrene class of compounds that includes quinine and lumefantrine. It appears to inhibit polymerisation of heme molecules (by the parasite enzyme "heme polymerase"), resulting in the parasite being poisoned by its own waste. Halofantrine has been shown to preferentially block open and inactivated HERG channels leading to some degree of cardiotoxicity.

Halofantrine Basic Attributes

Molecular Weight：

500.42

Exact Mass：

500.42

EC Number：

274-104-1

DSSTox ID：

DTXSID0023119

ATC Code：

P - Antiparasitic products, insecticides and repellents

Characteristics

PSA：

23.5

XLogP3：

8.9

Appearance：

White solid

Density：

1.244 g/cm3

Melting Point：

136-138ºC

Boiling Point：

596.2ºC at 760 mmHg

Flash Point：

314.4ºC

Refractive Index：

1.577

Water Solubility：

0.59mg/L(37 ºC)

Toxicity

Toxicity Summary：

Side effects incldue coughing noisy, rattling, troubled breathing, loss of appetite, aches and pain in joints, indigestion,and skin itching or rash.

Protein Binding：

60-70%;

Drug Information

Drug Indication：

For treatment of Severe malaria|FDA Label

Pharmacology：

Halofantrine is a synthetic antimalarial which acts as a blood schizonticide. It is effective against multi drug resistant (including mefloquine resistant) P. falciparum malaria.

MeSH：

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

Metabolism/Metabolites：

Hepatic

Biological Half-Life：

6-10 days

Mechanism of Action：

The mechanism of action of Halofantrine may be similar to that of chloroquine, quinine, and mefloquine; by forming toxic complexes with ferritoporphyrin IX that damage the membrane of the parasite.

MeSH Entry Terms：

1-(1,3-dichloro-6-trifluoromethyl-9-phenanthryl)-3-di(n-butyl)aminopropanol HCl

Halofantrine Use and Manufacturing

Methods of Manufacturing

2, 4-Dichloro-6-nitrobenzaldehyde and 4-trifluoromethylphenylacetic acid are condensed to obtain compound (I). Then reduce the nitro group to an amino group to obtain compound (II). Diazotization of nitrous acid is performed first, and then the ring is coupled to synthesize phenanthrene ring (Ⅲ) under the action of strong acid. This is a classic: Pschorr reaction. Then it is reduced to alcohol, and then oxidized to aldehyde (V) with lead acetate. Reformatski condensation is carried out with N, N-di-n-butyl bromoacetamide and zinc, and the product is reduced with diborane to obtain halofantrine. Under stirring, 14.0 g of halofantrine was added to a 50% aqueous solution containing 4.8 g of β-glycerophosphonic acid, 500 ml of ethanol was added, and the mixture was heated at about 100°C. The precipitated white precipitate was collected by filtration to obtain halofantrine glycerol phosphonate.

Uses

It is an old antimalarial drug discovered in the 1930s. Plasmodium falciparum is as effective as chloroquine and can cure patients infected with chloroquine-resistant parasites. Used for malaria.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:500.4
XLogP3:8.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:499.1656545
Monoisotopic Mass:499.1656545
Topological Polar Surface Area:23.5
Heavy Atom Count:33
Complexity:584
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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HALOFANTRINE

CAS No.: 69756-53-2

Grade: industrial Grade

Content: 98%

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