Hexachlorophene

Hexachlorophene
Skeletal formula of hexachlorophene
Ball-and-stick model of the hexachlorophene molecule
Clinical data
Trade names pHisoHex, Gamophen, Septisol, Turgex, Germa-Medica, Hexachlorophane, Almederm
ATC code
Legal status
Legal status
  • US: ℞-only for human use
  • Rx-only for human use
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.000.667 Edit this at Wikidata
Chemical and physical data
Formula C13H6Cl6O2
Molar mass 406.89 g·mol−1
3D model (JSmol)
Density 1.71 g/cm3
Melting point 163 to 165 °C (325 to 329 °F)
Boiling point 471 °C (880 °F)

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 a 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, plant bactericide, and acaricide.[1]

Commercialization

US, and removal from market

In 1972, the U.S. Food and Drug Administration (FDA) halted the production and distribution of products containing more than 1% of hexachlorophene.[2] After that point, most products that contain hexachlorophene were available only by prescription from a doctor.[3] The restrictions were enacted after 15 deaths in the United States and 39 deaths in France were reported following brain damage caused by hexachlorophene.[4]

Several companies manufactured over-the-counter preparations incorporating hexachlorophene. One product was Baby Magic Bath by The Mennen Company. Mennen recalled the product in 1971, and it was removed from retail distribution. Immediately after its withdrawal, there was an outbreak of Staphylococcus infections in hospital nurseries across the USA.[5]

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. In the US during the 1960s, both were available over the counter. After the ban was enacted, pHisoDerm was reformulated without hexachlorophene, and continued to be sold over-the-counter, while pHisoHex, which contained 3% hexachlorophene (three times the legal limit imposed in 1972),[4] 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. Another preparation, pHiso-Scrub, was 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 was the sole 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.[6]

The formula for Dial soap was modified to remove hexachlorophene after the FDA put an end to over-the-counter availability in 1972.[3]

Another company involved in the production of products with hexachlorophene was the now natural cosmetic company J.R. Watkins Company of Winona, Minnesota. At one time they produced "Watkins Cologne for Men" in a six ounce bottle. The label read: "For after bath or after shaving. Checks perspiration odor. Contains: Hexachlorophene".

Europe

In Germany, cosmetics containing hexachlorophene have been forbidden since 1985. In Austria, sale of drugs containing the substance has been forbidden since 1990.[7]

Production

Hexacholorophene is produced by alkylation of 2,4,5-trichlorophenol with formaldehyde. Related antiseptics are prepared similarly, e.g., bromochlorophene and dichlorophene.[1]

Safety

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,[1] but "embryotoxic and produces some teratogenic effects" according to the International Agency for Research on Cancer.[8] 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 this reaction goes without adequate cooling, TCDD becomes a major byproduct/contaminant. Examples of TCDD disaster due to Hexachlorophene production: Seveso disaster, Times Beach, Missouri, Etc.

Trade names

Trade names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, K-34, Septisol, Surofene.[9][10]

References

  1. 1 2 3 Fiege, H.; Voges, H.-M.; Hamamoto, T; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H.-J.; Garbe, D.; Paulus, W. (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3-527-30673-0.
  2. ↑ Germicide Limit Stirs Confusion, New York Times, September 24, 1972, pg. 53.
  3. 1 2 The Milwaukee Sentinel: "US Order Curbs Hexachlorophene" (UPI), September 23, 1972. From Google News.
  4. 1 2 Ocala Star Banner, "15 Deaths Cited In Use of Germ Killer, Hexachlorophene" (AP), March 21, 1973. From Google News.
  5. ↑ Dixon, RE; Kaslow, RA; Mallison, GF; Bennett, JV (1973). "Staphylococcal disease outbreaks in hospital nurseries in the United States--December 1971 through March 1972". Pediatrics. 51 (2): 413–7. PMID 4700144.
  6. ↑ http://www.ashp.org/menu/DrugShortages/DrugsNoLongerAvailable/Bulletin.aspx?id=1059.
  7. ↑ Rechtsinformationssystem des österreichischen Bundeskanzleramtes (in German)
  8. ↑ "Hexachlorophene". International Agency for Research on Cancer (IARC) - Summaries & Evaluations. IPCS Inchem. 20: 241. 1998 [1979].
  9. ↑ "Hexachlorophene". PharmGKB. Retrieved 2012-12-28.
  10. ↑ Dept. of Health, Education, and Welfare (1972). "Consumer news". Office of Consumer Affairs. 2 (21): 10.
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