HALOPROGIN Property

Melting point:

113-114°

Boiling point:

477.49°C (rough estimate)

Density 

1.9350 (estimate)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

RTECS 

KO1225000

Toxicity

LD50 in mice: >3 g/kg orally and s.c.; 510 mg/kg i.p. (Seki, 1963)

Hazard and Precautionary Statements (GHS)

HALOPROGIN Chemical Properties,Usage,Production

Originator

Halotex,Westwood,US,1972

Uses

Haloprogin is a topical antifungal agent used in the treatment of dermatophytic and monilial infections.

Uses

Antibacterial.

Definition

ChEBI: Haloprogin is an aromatic ether.

Indications

Haloprogin is used as an external drug for moderate dermatophyte infections (shingles), and it is effective for superficial candida infections. Synonyms of this drug are halotex, mycilan, micanden, and others.

Manufacturing Process

4.7 grams of 2,4,5-trichlorophenyl propargyl ether (MP 64° to 65°C) are added to an aqueous solution of cupro-ammonium complex salt which has been prepared by warming a mixture of 4.0 grams of cuprous chloride, 11.0 grams of ammonium carbonate and 20 cc of water to 50°C. The resulting admixture is shaken vigorously. The cuprous acetylide deposited is filtered, washed with water and suspended in 100 cc of water, and the suspension is mixed under agitation with a solution of 5.0 grams of iodine and 5.0 grams of potassium iodide in 15 cc of water. The mixture is stirred for a period of 1 hour. The precipitate is filtered, washed with water and extracted with ether. After the drying of the ethereal extract, the solvent is distilled off. Recrystallization of the residue from n-hexane gives about 5.6 grams of 2,4,5- trichlorophenyi iodopropargyl ether, MP 114° to 115°C.

brand name

Halotex (Westwood-Squibb).

Therapeutic Function

Antibacterial

General Description

3-Iodo-2-propynyl-2,4,5-trichlorophenyl ether (Halotex)crystallizes as white to pale yellow forms that are sparinglysoluble in water and very soluble in ethanol. It is an etherealderivative of a phenol. Haloprogin is used as a 1% cream forthe treatment of superficial tinea infections.
Formulations of haloprogin should be protected fromlight because the compound is photosensitive. Haloprogin isavailable as a solution and a cream, both in a 1% concentration.Haloprogin is probably not the first topical agent thatshould be recommended. Although the cure rates for topicalfungal infections are relatively high, they come at a highprice. The lesion typically worsens before it improves.Inflammation and painful irritation are common.

Synthesis

Haloprogin, 3-iodo-2-propinyl-2,4,5-trichlorophenyl ether (35.4.11), is synthesized by an iodide substitution using a mixture of iodine and potassium iodide and a cupric derivative of 2,4,5-trichlorophenylpropargyl ether (35.4.10), which is synthesized by a standard method from propargyl bromide and 2,4,5-trichlorophenol in the presence of sodium hydroxide.