Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ...

. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

ic odor. It is insoluble in water but dissolves in

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

, and

chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...

. In

medicine Medicine is the science and Praxis (process), practice of caring for patients, managing the Medical diagnosis, diagnosis, prognosis, Preventive medicine, prevention, therapy, treatment, Palliative care, palliation of their injury or disease, ...

, hexachlorophene is useful as a topical anti-infective and anti-bacterial agent. It is also used in agriculture as a soil

fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

plant Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...

bactericide, and

acaricide Acaricides are pesticides that kill members of the arachnid subclass '' Acari'', which includes ticks and mites. Acaricides are used both in medicine and agriculture, although the desired selective toxicity differs between the two fields. Termi ...

Production

Hexachlorophene is produced by alkylation of 2,4,5- trichlorophenol with

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

. Related antiseptics are prepared similarly, e.g., bromochlorophene and dichlorophene.

Safety

The LD50 (oral, rat) is 59 mg/kg, indicating that the compound is relatively toxic. It is not

mutagen In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in ...

ic 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 (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 Times Beach is a ghost town in St. Louis County, Missouri, St. Louis County, Missouri, United States, southwest of St. Louis, Missouri, St. Louis and east of Eureka, Missouri, Eureka. Once home to more than two thousand people, the town was co ...

, contamination incident exemplify the industrial hazards of hexachlorophene production.

Selective removal from market

France

In 1972, the "Bébé" brand of

baby powder Baby powder is an astringent powder (substance), powder used for preventing diaper rash and for Cosmetics, cosmetic uses. It may be composed of talc (in which case it is also called talcum powder), corn starch or potato starch. It may contain a ...

in France killed 39 babies. It also did great damage to the

central nervous system The central nervous system (CNS) is the part of the nervous system consisting primarily of the brain, spinal cord and retina. The CNS is so named because the brain integrates the received information and coordinates and influences the activity o ...

s 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 The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respo ...

(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. 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.
/ref> 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 Acne ( ), also known as ''acne vulgaris'', is a long-term Cutaneous condition, skin condition that occurs when Keratinocyte, dead skin cells and Sebum, oil from the skin clog hair follicles. Typical features of the condition include comedo, ...

, (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 The European Economic Community (EEC) was a regional organisation created by the Treaty of Rome of 1957,Today the largely rewritten treaty continues in force as the ''Treaty on the functioning of the European Union'', as renamed by the Lisbo ...

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 Sanofi S.A. is a French multinational pharmaceutical and healthcare company headquartered in Paris, France. The corporation was established in 1973 and merged with Synthélabo in 1999 to form Sanofi-Synthélabo. In 2004, Sanofi-Synthélabo merg ...

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). 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.

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.

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''.

References

{{Antiseptics and disinfectants Teratogens Chloroarenes Antiseptics Phenols