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Hexachlorophene

Systematic (IUPAC) name
2,2'-methylenebis(3,4,6-trichlorophenol)
Identifiers
CAS number	70-30-4
ATC code	D08AE01 QP52AG02
PubChem	3598
DrugBank	APRD00722
Chemical data
Formula	C13H6Cl6O2
Mol. mass	406.902 g/mol
SMILES	eMolecules & PubChem
Physical data
Melt. point	164 °C (327 °F)
Pharmacokinetic data
Bioavailability	?
Protein binding	92%
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?
Y(what is this?)  (verify)

Hexachlorophene, also known as Nabac, is a disinfectant. The compound occurs as a white to light-tan crystalline powder, which either is 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.

Hexachlorophene can be lethal from percutaneous (through the skin) absorption. Children may be specifically susceptible. Hexachlorophene (6.3%) was added to “baby powder” in France due to a manufacturing error. It caused encephalopathy and ulcerative skin lesions. 36 of 204 exposed children died within a few days of exposure.^[1]

Two companies manufactured over-the-counter preparations. One, by The Mennen Company, Morristown, NJ, was known as Baby Magic Bath. However, Mennen recalled the product, and all bottles were taken off retail shelves. Right after the withdrawal, there was an outbreak of Staphylococcus infections in hospitals across the USA.^{[citation needed]}

A commercial preparation of the drug, pHisoHex, was widely used as a very effective antibacterial skin cleanser in the treatment of acne. In the U.S. 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; it has since been discontinued.

In 1969, hexachlorophene became suspected of causing cancer. Around 1973 it was withdrawn from over-the-counter sales as a treatment for acne, and became a prescription drug. It was later determined not to cause cancer^{[citation needed]}. Nevertheless, hexachlorophene soap is not available over the counter today, because once a product has been withdrawn by the FDA it is virtually impossible for it to be reinstated, even after invalidation of the reasons for its removal. The MSDS still lists this compound as an experimental teratogen.

Possibly because of the previous questions concerning its effects, most dermatologists today do not prescribe it for acne treatment. In Australia, it remains freely available from all pharmacies and supermarkets without prescription.

Several substitute products (including triclosan) were developed, but none had the germ-killing capability of hexachlorophene.

[edit] Alternative names

Alternative names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, Septisol, Surofene.^[2]

[edit] References

1. ^ "Proceedings of the International Conference on Occupational & Environmental Exposures of Skin to Chemicals: Science & Policy". CDC. http://www.cdc.gov/niosh/topics/skin/conference/s1t2.html. Retrieved November 17, 2009. 
2. ^ "Hexachlorophene". INCHEM — IPCS (International Program on Chemical Safety). October 2004. http://www.inchem.org/documents/icsc/icsc/eics0161.htm. Retrieved 2008-03-27.