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   » » Wiki: Hexachlorophene
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Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a . The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly odor. It is insoluble in water but dissolves in , , , and . In , hexachlorophene is useful as a anti-infective and anti-bacterial agent. It is also used in agriculture as a soil , , and .

(2025). 9783527306732, Wiley-VCH.


Production
Hexacholorophene is produced by alkylation of 2,4,5- with . Related antiseptics are prepared similarly, e.g., bromochlorophene and .


Safety
The LD50 (oral, rat) is 59 mg/kg, indicating that the compound is relatively toxic. It is not nor 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 (TCDD) 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- and formaldehyde is exothermic. If the reaction occurs without adequate cooling, TCDD is produced in significant quantities as a byproduct and contaminant. The and the Times Beach, Missouri, contamination incident exemplify the industrial hazards of hexachlorophene production.


Selective removal from market

France
In 1972, the "Bébé" brand of 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 mistakenly manufactured with 6% hexachlorophene. This industrial accident directly led to the removal of hexachlorophene from consumer products worldwide.


United States
In 1972, the U.S. Food and Drug Administration (FDA) halted production and distribution of products containing more than 1% hexachlorophene. Limit Stirs Confusion, New York Times, September 24, 1972, pg. 53. After that change, most products containing hexachlorophene were available only with a doctor's prescription. The restrictions were enacted after 15 deaths in the United States, and the 39 deaths in France mentioned above, were reported following brain damage caused by hexachlorophene. Ocala Star Banner, "15 Deaths Cited In Use of Germ Killer, Hexachlorophene" (AP), March 21, 1973. From Google News.

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, and pHisoHex, were widely used as antibacterial skin cleansers in the treatment of , (with pHisoDerm developed for those allergic to the active ingredients in pHisoHex). 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, (which contained 3% hexachlorophene - 3 times the legal limit imposed in 1972), 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 to dry and peel away acne lesions whilst pHiso-Scrub, a hexachlorophene-impregnated sponge for scrubbing, has since been discontinued. Several substitute products (including ) were developed, but none had the germ-killing capability of hexachlorophene. ( became the sole European manufacturer of pHisoHex, while owns the pHisoDerm brand today. Sanofi-Aventis discontinued production of several forms of pHisoHex in August 2009 and discontinued all production of pHisoHex in September 2013).

The formula for Dial soap was modified to remove hexachlorophene after the FDA ended over-the-counter availability in 1972.

discontinued toothpaste brand at one time contained hexachlorophene. Another U.S.A. brand of toothpaste containing hexachlorophene in the early 1960's was Stripe.


Germany
In Germany, cosmetics containing hexachlorophene have been banned since 1985.


Austria
In Austria, the sale of drugs containing the substance has been banned since 1990. Rechtsinformationssystem des österreichischen Bundeskanzleramtes


Trade names
Trade names for hexachlorophene include: Acigena, Almederm, AT7 (dial soap), AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, K-34, Septisol, Surofene, M3.

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