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Hexachlorophene

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Hexachlorophene
Skeletal formula of hexachlorophene
Ball-and-stick model of the hexachlorophene molecule
Clinical data
Trade namespHisoHex, Gamophen, Septisol, Turgex, Germa-Medica, Hexachlorophane, Almederm
ATC code
Legal status
Legal status
  • US: Rx-only for human use
  • Rx-Only for human use
Identifiers
  • 2,2'-methylenebis(3,4,6-trichlorophenol)-3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.667 Edit this at Wikidata
Chemical and physical data
FormulaC13H6Cl6O2
Molar mass406.89 g·mol−1
3D model (JSmol)
Density1.71 g/cm3
Melting point163 to 165 °C (325 to 329 °F)
Boiling point471 °C (880 °F)
  • C1=C(C(=C(C(=C1Cl)Cl)CC2=C(C(=CC(=C2Cl)Cl)Cl)O)O)Cl
  • InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2
  • Key:ACGUYXCXAPNIKK-UHFFFAOYSA-N

Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white solid (although commercial samples can be off-white) and can be odorless or possess a slightly phenolic odor. In medicine, hexachlorophene is very 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 and removal from U.S. market

US

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 effective 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

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 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. Its usefulness has been limited by this toxicity, not other factors such as mutagenicity nor teratogenicity.[1][failed verification]

Physical properties

Hexachlorophene is insoluble in water, and soluble in acetone, ethanol, diethyl ether, and chloroform.

Trade names

Trade names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, K-34, Septisol, Surofene.[8][9]

References

  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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 Template:De icon
  8. ^ "Hexachlorophene". PharmGKB. Retrieved 2012-12-28.
  9. ^ Dept. of Health, Education, and Welfare (1972). "Consumer news". Office of Consumer Affairs. Volume 2 (Issue 21): 10. {{cite journal}}: |issue= has extra text (help); |volume= has extra text (help)CS1 maint: multiple names: authors list (link)
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