Originator
Halotex,Westwood,US,1972
Uses
Haloprogin is a topical antifungal agent used in the treatment of dermatophytic and monilial infections.
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.
