Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. In medicine, hexachlorophene is useful as a topical anti-infective, anti-bacterial agent, often used in soaps and toothpaste. It is also used in agriculture as a soil fungicide, plantbactericide, and acaricide.
Removal from market
French deaths
In 1972, the "Bébé" brand of baby powder in France killed 39 babies. It also did great damage to the central nervous systems of several hundred other babies. The batch of toxic "Bébé" brand of powder was manufactured with 6% hexachlorophene. This industrial accident directly led to the removal of hexachlorophene from consumer products across the world.
In 1972, the U.S. Food and Drug Administration halted the production and distribution of products containing more than 1% of hexachlorophene. After that point, most products that contain hexachlorophene were available only with a doctor's prescription. The restrictions were enacted after 15 deaths in the United States and 39 deaths in France were reported following brain damage caused by hexachlorophene. Several companies manufactured over-the-counter preparations which utilised hexachlorophene in their formulations. One product, Baby Magic Bath by The Mennen Company, was recalled in 1971, and removed from retail distribution. Two commercial preparations using hexachlorophene, pHisoDerm and pHisoHex, were widely used as antibacterial skin cleansers in the treatment of acne,. During the 1960s, both were available over the counter in the US. After the ban, pHisoDerm was reformulated without hexachlorophene, and continued to be sold over-the-counter, while pHisoHex,, became available as a prescription body wash. In the European Community countries during the 1970s and 1980s, pHisoHex remained available over the counter. A related product, pHisoAc, was used as a skin mask to dry and peel away acne lesions whilst pHiso-Scrub, a hexachlorophene-impregnated sponge for scrubbing, has since been discontinued. Several substitute products were developed, but none had the germ-killing capability of hexachlorophene.. The formula for Dial soap was modified to remove hexachlorophene after the FDA put an end to over-the-counter availability in 1972. Bristol-Myers' discontinued Ipana toothpaste brand at one time contained hexachlorophene. Another company involved in the production of products with hexachlorophene was cosmetic company, J.R. Watkins Company of Winona, Minnesota. They had previously produced "Watkins Cologne for Men".
Germany
In Germany, cosmetics containing hexachlorophene have been forbidden since 1985.
Austria
In Austria, sale of drugs containing the substance has been forbidden since 1990.
Production
Hexacholorophene is produced by alkylation of 2,4,5-trichlorophenol with formaldehyde. Related antiseptics are prepared similarly, e.g., bromochlorophene and dichlorophene.
Safety
The LD50 is 59 mg/kg, indicating that the compound is relatively toxic. It is not mutagenic nor teratogenic according to Ullmann's Encyclopedia, but "embryotoxic and produces some teratogenic effects" according to the International Agency for Research on Cancer. 2,3,7,8-Tetrachlorodibenzodioxin is always a contaminant in this compound's production. Several accidents releasing many kilograms of TCDD have been reported. The reaction between 2,4,5-trichlorophenol and formaldehyde is exothermic. If the reaction occurs without adequate cooling, TCDD is produced in significant quantities as a byproduct and contaminant. The Seveso disaster and the Times Beach, Missouri contamination incident exemplify the industrial hazards of hexachlorophene production.
