Hexachlorophene

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Hexachlorophene
QP52AG02 (WHO)
Legal status
Legal status
  • US: ℞-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
JSmol)
Density1.71 g/cm3
Melting point163 to 165 °C (325 to 329 °F)
Boiling point471 °C (880 °F)
SMILES
  • 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

topical anti-infective and anti-bacterial agent. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide.[1]

Production

Hexacholorophene is produced by alkylation of 2,4,5-

dichlorophene.[1]

Safety

The

teratogenic according to Ullmann's Encyclopedia,[1] but "embryotoxic and produces some teratogenic effects" according to the International Agency for Research on Cancer.[2] 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.[citation needed
]

Selective removal from market

France

In 1972, the "Bébé" brand of

industrial accident directly led to the removal of hexachlorophene from consumer products worldwide.[3][4]

United States

In 1972, the U.S. Food and Drug Administration (FDA) halted production and distribution of products containing more than 1% hexachlorophene.[5] After that change, most products containing hexachlorophene were available only with a doctor's prescription.[6] 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.[7]

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.[citation needed
]

Two commercial preparations using 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).[8]

The formula for Dial soap was modified to remove hexachlorophene after the FDA ended over-the-counter availability in 1972.[6]

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. [9]

Germany

In Germany, cosmetics containing hexachlorophene have been banned since 1985.[citation needed]

Austria

In Austria, the sale of drugs containing the substance has been banned since 1990.[10]

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.[11][12]

References

  1. ^
    ISBN 3-527-30673-0
    .
  2. ^ "Hexachlorophene". International Agency for Research on Cancer (IARC) - Summaries & Evaluations. 20. IPCS Inchem: 241. 1998 [1979].
  3. ^ "Talcum Suspected in Deaths of 21 French Babies". No. 29 August 1972. New York Times. p. 10. Retrieved 18 March 2020.
  4. ^ "FDA CURBS USE OF GERMICIDE TIED TO INFANT DEATHS". No. 23 September 1972. New York Times. p. 1. Retrieved 18 March 2020.
  5. Germicide
    Limit Stirs Confusion    , New York Times, September 24, 1972, pg. 53.
  6. ^ a b "The Milwaukee Sentinel: "US Order Curbs Hexachlorophene" (UPI), September 23, 1972. From Google News". Archived from the original on April 2, 2016. Retrieved June 16, 2015.
  7. ^ a b Ocala Star Banner, "15 Deaths Cited In Use of Germ Killer, Hexachlorophene" (AP), March 21, 1973. From Google News.
  8. ^ "Drug Shortages". American Society of Health-System Pharmacists. Archived from the original on 10 September 2014.
  9. ^ "1959 Ipana Toothpaste Ad". YouTube. 30 December 2011.
  10. ^ Rechtsinformationssystem des österreichischen Bundeskanzleramtes (in German)
  11. ^ "Hexachlorophene". PharmGKB. Retrieved 2012-12-28.
  12. ^ Dept. of Health, Education, and Welfare (1972). "Consumer news". Office of Consumer Affairs. 2 (21): 10.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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