Hexachlorophene, 2,2'-methylenebis (3,4,6-trichlorophe-nol); 2,2'-dihydroxy-3,5,6,3',5', 6'-hexachlorodiphenyl-methane (Gamophen, Surgicon, pHisoHex) is a white to light-tan crystalline powder that is insoluble in water but is soluble in alcohol and most other organic solvents. A biphenol such as hexachlorophene will, in general, possess greater potency than a monophenol. In addition, as expected, the increased degree of chlorination of hexachlorophene increases its antiseptic potency further.
Hexachlorophene is easily adsorbed onto the skin and enters the sebaceous glands. Because of this, topical application elicits a prolonged antiseptic effect, even in low concentrations. Hexachlorophene is used in concentrations of 2% to 3% in soaps, detergent creams, lotions, and shampoos for various antiseptic uses. It is, in general, effective against Gram-positive bacteria, but many Gram-negative bacteria are resistant.
The systemic toxicity of hexachlorophene in animals after oral and parenteral administration had been known for some time, but in the late 1960s and early 1970s, reports of neurotoxicity in infants bathed in hexachlorophene and in burn patients cleansed with the agent prompted the FDA to ban its use in over-the-counter (OTC) antiseptic and cosmetic preparations.10 Hexachlorophene is still available by prescription.
Cresol is actually a mixture of three isomeric methylphenols:
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The mixture occurs as a yellow to brownish yellow liquid that has a characteristic odor of creosote. Cresol is obtained from coal tar or petroleum by alkaline extraction into aqueous medium, acidification, and fractional distillation. The mixture is an inexpensive antiseptic and disinfectant. It possesses a phenol coefficient of 2.5. Cresol is sparingly soluble in water, although alcohols and other organic solvents will solubilize it. The drawback to its use as an antiseptic is its unpleasant odor.
4-Chloro-3-methylphenol occurs as colorless crystals. Chlorocresol is only slightly soluble in water. At the low concentration that can be achieved in aqueous media, the compound is only useful as a preservative.
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