Hexachlorophene

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Hexachlorophene
Systematic (IUPAC) name
3,4,6-trichloro-2- [(2,3,5-trichloro-6-hydroxy-phenyl) methyl]phenol
Identifiers
CAS number	70-30-4
ATC code	D08 AE01
PubChem	3598
DrugBank	APRD00722
Chemical data
Formula	C₁₃H₆Cl₆O₂
Mol. weight	406.902 g/mol
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	?

Hexachlorophene, also known as Nabac, is an antiseptic agent. The compound occurs as a white to light tan crystalline powder which is either 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. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide.

Two companies had over the counter brands available. One, by The Mennen Company, Morristown, NJ, was known as Baby Magic Bath. 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]}.

During the 1960s, a commercial preparation of the drug, pHisoHex, was available over the counter. pHisoHex was widely used as a very effective antibacterial skin cleanser in the treatment of acne. A related product, pHisoAc, was used as a skin mask to dry and peel away acne lesions. Another known as Phiso-Scrub was a hexachlorophene-impregnated sponge for scrubbing; it has since been discontinued.

In 1969, hexachlorophene became suspected of causing cancer. In 1972, a study by Dr. Cyril Moore and his research assistant, Dr. Wendy Cammar, suggested that hexachlorophene in the liquid cleaner pHisoHex (up to then widely used in newborn nurseries) was toxic to mitochondria, inhibited ATP production in the brain, and resulted in myelin edema. Around 1973, it was withdrawn from over-the-counter sales as a treatment for acne and became a prescription drug.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. Nevertheless, hexachlorophene soap is still not available over the counter today, because once a product has been withdrawn by the FDA, it is virtually impossible for it to be reinstated even after invalidation of the reasons for its removal.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.

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