Hexachlorophene
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| Image:Hexachlorophene.png | |
| Hexachlorophene
| |
| Systematic (IUPAC) name | |
| 3,4,6-trichloro-2- [(2,3,5-trichloro-6-hydroxy-phenyl) methyl]phenol | |
| Identifiers | |
| CAS number | |
| ATC code | D08 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C13H6Cl6O2 |
| Mol. mass | 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. Around 1973 it was withdrawn from over-the-counter sales as a treatment for acne and became a prescription drug.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 Nevertheless, hexachlorophene soap is not available over the counter today, because once a product has been withdrawn by the FDA it is virtually impossible for it to be reinstated, even after invalidation of the reasons for its removal.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.
Antiseptics and disinfectants (D08) | |
|---|---|
| Acridine derivatives | Ethacridine lactate - Aminoacridine - Euflavine |
| Biguanides and amidines | Dibrompropamidine - Chlorhexidine - Propamidine - Hexamidine - Polihexanide |
| Phenol and derivatives | Hexachlorophene - Policresulen - Phenol - Triclosan - Chloroxylenol - Biphenylol |
| Nitrofuran derivatives | Nitrofurazone |
| Iodine products | Iodine/octylphenoxypolyglycolether - Povidone-iodine - Diiodohydroxypropane |
| Quinoline derivatives | Dequalinium - Chlorquinaldol - Oxyquinoline - Clioquinol |
| Quaternary ammonium compounds | Benzalkonium - Cetrimonium - Cetylpyridinium - Cetrimide - Benzoxonium chloride - Didecyldimethylammonium chloride |
| Mercurial products | Mercuric amidochloride - Phenylmercuric borate - Mercuric chloride - Mercurochrome - Thiomersal - Mercuric iodide |
| Silver compounds | Silver nitrate |
| Others | Hydrogen peroxide - Eosin - Propanol - Tosylchloramide sodium - Isopropanol - Potassium permanganate - Sodium hypochlorite - Ethanol |
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

