Hexachlorophene

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Hexachlorophene
Skeletal formula of hexachlorophene
Ball-and-stick model of the hexachlorophene molecule
Systematic (IUPAC) name
2,2'-methylenebis(3,4,6-trichlorophenol)-3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
Clinical data
Trade names pHisoHex, Gamophen, Septisol, Turgex, Germa-Medica, Hexachlorophane, Almederm
Legal status
Legal status
  • US: Rx-only for human use
  • Rx-Only for human use
Identifiers
CAS Number 70-30-4
ATC code D08AE01 (WHO) QP52AG02 (WHO)
PubChem CID 3598
DrugBank DB00756
ChemSpider 3472
UNII IWW5FV6NK2
KEGG D00859
ChEBI CHEBI:5693
ChEMBL CHEMBL496
Chemical data
Formula C13H6Cl6O2
Molar mass 406.89 g·mol−1
Physical data
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[edit]

US, and removal from market[edit]

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 reports of 15 deaths in the United States and 39 deaths in France were reported following brain damage caused by hexachlorophene.[4]

At least two 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 the withdrawal, there was an outbreak of Staphylococcus infections in hospitals 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 (and remain available today) as a prescription body wash. In the European Community countries during the 1970s and 1980s, pHisoHex was 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 changed to remove hexachlorophene after the FDA put an end to over-the-counter availability in 1972.[3]

Europe[edit]

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[edit]

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

Safety[edit]

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 Encyclopaedia,[1] but "embryotoxic and produces some teratogenic effects" according to the International Agency for Research on Cancer.[8]

Trade names[edit]

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[edit]

  1. ^ a b c 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. ^ a b The Milwaukee Sentinel: "US Order Curbs Hexachlorophene" (UPI), September 23, 1972. From Google News.
  4. ^ a b 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 (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.