- Hexachlorophene
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Hexachlorophene Systematic (IUPAC) name 2,2'-methylenebis(3,4,6-trichlorophenol) Clinical data Trade names Phisohex AHFS/Drugs.com monograph Pregnancy cat. ? Legal status ? Identifiers CAS number 70-30-4 ATC code D08AE01 QP52AG02 PubChem CID 3598 DrugBank APRD00722 ChemSpider 3472 UNII IWW5FV6NK2 KEGG D00859 ChEMBL CHEMBL496 Chemical data Formula C13H6Cl6O2 Mol. mass 406.902 g/mol SMILES eMolecules & PubChem Physical data Melt. point 164 °C (327 °F) (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 products 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, or possibly contaminating dioxins, 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, and studies determined that oral ingestion of hexachlorophene led to weakness and paralysis in laboratory rats. In 1973, after studies found relatively high concentrations of hexachlorophene in the blood of neonates washed with a 3% solution it was withdrawn from over-the-counter sales, though still available by prescription [2]. A 1978 study undertaken by the U.S. National Institutes of Health[3], indicated that hexachlorophene does not cause cancer. However, 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.
Alternative names
Alternative names for hexachlorophene include: Acigena, Almederm, AT7, AT17, Bilevon, Exofene, Fostril, Gamophen, G-11, Germa-Medica, Hexosan, Septisol, Surofene.[4]
References
- ^ "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.
- ^ "Evaluation of Drug Safety and Efficacy. Hexachlorophene: Case in Point: The Saga of Hexachlorophene". NIH. http://jcp.sagepub.com/content/13/11/437.full.pdf+html. Retrieved September 21, 2010.
- ^ "BIOASSAY OF HEXACHLOROPHENE FOR POSSIBLE CARCINOGENICITY". NIH. http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr040.pdf. Retrieved August 30, 2010.
- ^ "Hexachlorophene". INCHEM — IPCS (International Program on Chemical Safety). October 2004. http://www.inchem.org/documents/icsc/icsc/eics0161.htm. Retrieved 2008-03-27.
Antiseptics and disinfectants (D08) Acridine derivatives Biguanides and amidines Phenol and derivatives Nitrofuran derivatives NitrofurazoneIodine products Quinoline derivatives Quaternary ammonium compounds Mercurial products Silver compounds Alcohols Other Categories:- Teratogens
- Organochlorides
- Antiseptics
- Synthetic phenolic drugs
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