Hexachlorophene
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| Pharmacokinetic data | |
| Protein binding | 92% |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.000.667 |
| Chemical and physical data | |
| Formula | C13H6Cl6O2 |
| Molar mass | 406.902 g/mol g·mol−1 |
| Melting point | 164 °C (327 °F) |
Hexachlorophene, also known as Nabac, is a disinfectant related to the herbicides 2,4,5-T and 2,4-D[1]. 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 (including Dial, for a time, at 1%) and toothpastes. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide. It is readily absorbed through the human epidermis (skin).
According to United States Environmental Protection Agency research chemists August Curley and Robert Hawk, hexachlorophene "caused cerebral swelling and brain damage in rats and was found in the blood of human beings."[2] There were signs of toxicity as far back as 1959, when a newborn was bathed in a hexachlorophene solution, as was common practice, and broke out with sores, and "his arms, legs, and face began a slight, uncontrollable twitching. Slowly over the days, the twitching became more pronounced and then turned into full-scale convulsions"[3], though under Food and Drug Administration pressure, the manufacturer placed "a mild warning" indicating "that the fluid should be throughly washed off." John G. Fuller wrote "[a] statement like this would have been more appropriate: UNLESS YOU RINSE THIS OFF, YOU OR YOUR BABY CAN GO INTO CONVULSIONS. HEXACHLOROPHENE CAN BUILD UP IN YOUR BLOOD. BRAIN LESIONS AND CEREBRAL SWELLINGS HAVE OCCURRED ON THE SKIN OF LABORATORY RATS FROM SURFACE USE ON INTACT SKIN. ACCIDENTAL SWALLOWING OF PHISOHEX CAN KILL YOU."[4]
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.
A commercial 3% preparation of the drug, pHisoHex, was widely used as a antibacterial skin cleanser in the treatment of acne. Ironically, it caused chloasma, or a melanosis of the face, on many of its users[5]. 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. The MSDS lists this compound as a teratogen.
Possibly because of the previous adverse effects, most dermatologists today do not prescribe it for acne treatment. In Australia, it remains freely available from all pharmacies without prescription.
Several substitute products (including triclosan) were developed, but none had the germ-killing capability of hexachlorophene. They did, however, cause less chloasma and convulsions.
Alternative names
Alternative names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, Septisol, Surofene.[6]
References
- ^ Fuller, John G. "200,000,000 Guinea Pigs." New York: G. P. Putnam's Sons, 1972. p. 44.
- ^ Ibid., p. 262.
- ^ Ibid., p. 262
- ^ Ibid., p. 263. Emphasis in original.
- ^ Ibid, pp. 263, and V.D. Newcomer, 1961
- ^ "Hexachlorophene". INCHEM — IPCS (International Program on Chemical Safety). 2004. Retrieved 2008-03-27.
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