Hexachlorophene

hexachlorophene
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
  • US: Rx-only for human use
  • Rx-Only for human use
Identifiers
70-30-4
PubChem CID 3598
DrugBank DB00756
ChemSpider 3472
UNII IWW5FV6NK2
KEGG D00859
ChEBI CHEBI:CHEBI:5693
ChEMBL CHEMBLCHEMBL496
Chemical data
Formula C13H6Cl6O2
406.903503 g/mol
Physical data
Density 1.71 g/cm3
Melting point 163 to 165 °C (325 to 329 °F)
Boiling point 471 °C (880 °F)
Insoluble in water. Soluble in acetone, ethanol, ether and chloroform. mg/mL (20 °C)

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 market

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.[2]

A commercial preparation using hexachlorophene, pHisoHex, was widely used as an effective antibacterial skin cleanser in the treatment of acne. In the US during the 1960s, it was available over the counter, and remains available as a prescription body wash. In the E.U. during the 1970s and 1980s, it 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.

The formula for Dial soap was changed to remove hexachlorophene after the U.S. Food and Drug Administration put an end to over-the-counter availability in 1972.[3]

Sanofi-Aventis was the sole manufacturer of hexachlorophene cleanser (pHisoHex). Sanofi-Aventis discontinued production of several forms of pHisoHex in August 2009 and discontinued all production of pHisoHex in September 2013. [4]

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]

Trade names

Trade names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, Septisol, Surofene.[5]

References

  1. ↑ 1.0 1.1 1.2 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. ↑ 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.
  3. ↑ http://news.google.com/newspapers?id=hHRQAAAAIBAJ&sjid=YhEEAAAAIBAJ&pg=3621,2685761&dq=dial+hexachlorophene&hl=en
  4. ↑ http://www.ashp.org/menu/DrugShortages/DrugsNoLongerAvailable/Bulletin.aspx?id=1059.
  5. ↑ "Hexachlorophene". PharmGKB. Retrieved 2012-012-28. Check date values in: |accessdate= (help)