hexachlorophene

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

The LD50 (oral, rat) 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.{{Cite journal |year=1998 |title=Hexachlorophene |url=http://www.inchem.org/documents/iarc/vol20/hexachlorophene.html |journal=International Agency for Research on Cancer (IARC) - Summaries & Evaluations |publisher=IPCS Inchem |volume=20 |pages=241 |orig-year=1979}} 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-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.{{cn|date=January 2025}}

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 mistakenly manufactured with 6% hexachlorophene. This industrial accident directly led to the removal of hexachlorophene from consumer products worldwide.{{Cite news |title=Talcum Suspected in Deaths of 21 French Babies |url=https://timesmachine.nytimes.com/timesmachine/1972/08/29/issue.html |access-date=18 March 2020 |page=10 |issue=29 August 1972 |agency=New York Times}}{{Cite news |title=FDA CURBS USE OF GERMICIDE TIED TO INFANT DEATHS |url=https://timesmachine.nytimes.com/timesmachine/1972/09/23/issue.html |access-date=18 March 2020 |page=1 |issue=23 September 1972 |agency=New York Times}}

In 1972, the U.S. Food and Drug Administration (FDA) halted production and distribution of products containing more than 1% hexachlorophene.Germicide 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.{{Cite web |title=The Milwaukee Sentinel: "US Order Curbs Hexachlorophene" (UPI), September 23, 1972. From Google News. |url=https://news.google.com/newspapers?id=hHRQAAAAIBAJ&sjid=YhEEAAAAIBAJ&pg=3621,2685761&dq=dial+hexachlorophene&hl=en |url-status=dead |archive-url=https://web.archive.org/web/20160402235034/https://news.google.com/newspapers?id=hHRQAAAAIBAJ&sjid=YhEEAAAAIBAJ&pg=3621,2685761&dq=dial+hexachlorophene&hl=en |archive-date=April 2, 2016 |access-date=June 16, 2015}} 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.[https://news.google.com/newspapers?nid=1356&dat=19730321&id=dI5PAAAAIBAJ&sjid=fQUEAAAAIBAJ&pg=7064,4239653&hl=en 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.{{cn|date=January 2025}}

Two commercial preparations using hexachlorophene, pHisoDerm and pHisoHex, were widely used as antibacterial skin cleansers in the treatment of acne, (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 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 (including triclosan) were developed, but none had the germ-killing capability of hexachlorophene. (Sanofi-Aventis became the sole European manufacturer of pHisoHex, while The Mentholatum Company 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).{{Cite web |title=Drug Shortages |url=http://www.ashp.org/menu/DrugShortages/DrugsNoLongerAvailable/Bulletin.aspx?id=1059 |archive-url=https://web.archive.org/web/20140910195747/http://www.ashp.org/menu/DrugShortages/DrugsNoLongerAvailable/Bulletin.aspx?id=1059 |archive-date=10 September 2014 |website=American Society of Health-System Pharmacists}}

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

Bristol-Myers' discontinued Ipana toothpaste brand at one time contained hexachlorophene. Another U.S.A. brand of toothpaste containing hexachlorophene in the early 1960's was Stripe. {{Cite web |date=30 December 2011 |title=1959 Ipana Toothpaste Ad |url=https://www.youtube.com/watch?v=7xHRt1lPqNA |website=YouTube}}

In Germany, cosmetics containing hexachlorophene have been banned since 1985.{{cn|date=January 2025}}

In Austria, the sale of drugs containing the substance has been banned since 1990.[http://www.ris.bka.gv.at/Dokumente/Bundesnormen/NOR12134873/NOR12134873.html Rechtsinformationssystem des österreichischen Bundeskanzleramtes] {{in lang|de}}

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.{{Cite web |title=Hexachlorophene |url=http://www.pharmgkb.org/drug/PA449871#tabview=tab1&subtab=31 |access-date=2012-12-28 |publisher=PharmGKB}}{{Cite journal |last=Dept. of Health, Education, and Welfare |date=1972 |title=Consumer news |journal=Office of Consumer Affairs |volume=2 |issue=21 |page=10}}

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{{Antiseptics and disinfectants}}

Category:Teratogens

Category:Chloroarenes

Category:Antiseptics

Category:Phenols