Hexachlorophene

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hexachlorophene
Hexachlorophene.png
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 namespHisoHex, Gamophen, Septisol, Turgex, Germa-Medica, Hexachlorophane, Almederm
Legal status?
Identifiers
CAS number70-30-4
ATC code?
PubChemCID 3598
DrugBankDB00756
ChemSpider3472
UNIIIWW5FV6NK2
KEGGD00859
ChEBICHEBI:CHEBI:5693
ChEMBLCHEMBLCHEMBL496
Chemical data
FormulaC13H6Cl6O2 
Mol. mass406.903503 g/mol
Physical data
Density1.71 g/cm³
Melt. point163–165 °C (325–329 °F)
Boiling point471 °C (880 °F)
Solubility in waterInsoluble in water. Soluble in acetone, ethanol, ether and chloroform. mg/mL (20 °C)
 
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hexachlorophene
Hexachlorophene.png
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 namespHisoHex, Gamophen, Septisol, Turgex, Germa-Medica, Hexachlorophane, Almederm
Legal status?
Identifiers
CAS number70-30-4
ATC code?
PubChemCID 3598
DrugBankDB00756
ChemSpider3472
UNIIIWW5FV6NK2
KEGGD00859
ChEBICHEBI:CHEBI:5693
ChEMBLCHEMBLCHEMBL496
Chemical data
FormulaC13H6Cl6O2 
Mol. mass406.903503 g/mol
Physical data
Density1.71 g/cm³
Melt. point163–165 °C (325–329 °F)
Boiling point471 °C (880 °F)
Solubility in waterInsoluble 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 produces 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[edit]

Two companies manufactured over-the-counter preparations. 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 of the drug, 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]

Production[edit]

It is produced by alkylation of 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. Its usefulness has been limited by this toxicity, not other factors such as mutagenicity nor teratogenicity.[1]

Trade names[edit]

Trade names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, Septisol, Surofene.[4]

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. ^ 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. ^ "Hexachlorophene". PharmGKB. Retrieved 2012-012-28.