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The monobenzyl ether in HQ is the substance used to cause permanent depigmentation of normal skin It is often used in vitiligo patients to permanently depigment the skin surrounding depigmented areas when repigmentation is not feasible and the depigmented areas are disfiguring Monobenzone (Fig 33-12) is metabolized inside cells into quinine, which acts by permanently damaging the melanocytes79 It is usually prepared at a concentration of 20% Brand names include Monobenzon, Dermochinona, Leucodinine, Carmifal, Depigman, Superlite, and Pigmex It is applied 2 or 3 times daily on pigmented skin, with depigmentation beginning around 6 to 12 months of treatment Transfer of the agent can occur to anyone who touches the medication; therefore, contact with others should be avoided for up to 3 hours after application80 Potential side effects include contact dermatitis, conjunctival melanosis, skin lightening in untreated areas,81 the possibility of an unwanted repigmentation starting from
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FIGURE 33-10 The chemical structure of azelaic acid
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Chemically known as 4-hydroxyanisole, mequinol is a derivative of HQ (Fig 33-11) Its exact mechanism of
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FIGURE 33-12 The chemical structure of monobenzone a derivative of hydroquinone
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follicular melanocytes, and the need for lifelong total photoprotection Because this agent is cytotoxic to melanocytes, it must be stressed that after depigmentation therapy with this agent, future attempts at repigmentation treatment will be completely ineffective
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N-Acetyl-4-S-cysteaminylphenol is a melanocytotoxic agent consisting of phenolic and catecholic compounds with potent depigmenting properties A study in which 12 patients with melasma were treated with a daily application of 4% N-acetyl-4-Scysteaminylphenol showed significant reduction in pigmentation, with results being visible as early as 2 to 4 weeks after therapy82
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Antioxidants are popular additives in skin care preparations for several reasons In addition to exhibiting antiaging, anticarcinogenic, and anti-inflammatory activities, they may also decrease pigmentation that occurs after exposure to UV light83 This may be useful in the treatment of melasma Research on vitiligo has shown that antioxidants may affect melanin production A comparison of normal melanocytes with melanocytes from vitiligo patients has demonstrated lower catalase activity and higher vitamin E and ubiquinone levels in the vitiligo patients suggesting that an imbalance in the antioxidant status and increase in the intracellular peroxide levels could play a role in vitiligo84 In addition, antioxidants, including GSH, a naturally-occurring antioxidant involved in regulating melanin synthesis,85 have been shown to inhibit or delay hyperpigmentation86 In support of these findings, a study by Yokozawa and Kim86 demonstrated that an antioxidant, piceatannol (PICE), could inhibit mushroom tyrosinase PICE (Fig 33-13) is a phenolic compound derived from resveratrol, which
FIGURE 33-13 The chemical structure of piceatannol (PICE) a derivative of resveratrol
is found in grapes and red wine It has antioxidative, antitumorigenic, and apoptosis-inducing effects In this study, investigators found that PICE inhibited melanogenesis and displayed potent antioxidant properties The authors concluded that the antioxidant activity played a major role in the inhibition of melanin production However, some studies have shown that some antioxidants increase skin pigmentation, so the individual properties of each antioxidant should be considered before using them to decrease skin pigmentation87 Inflammation has long been known to lead to skin pigmentation, especially in darker skin types Prostaglandins, which are produced during inflammation, may play a role in skin pigmentation Indeed, this may be one of the mechanisms by which inflammation can exacerbate melasma Maeda et al proposed that trans-4-aminomethylcyclohexanecarboxylic acid (trans-AMCHA or tranexamic acid), a plasmin inhibitor, decreases tyrosinase activity in the melanocytes via reduction in prostaglandin synthesis, thereby preventing UV-induced pigmentation in guinea pigs Localized intradermal microinjections of tranexamic acid have been used in an Asian study with some success88 However, more studies are needed to determine the efficacy and safety of this treatment Latanoprost and Bimatoprost, analogues of prostaglandin F2 (PGF2 ), are used as intraocular pressure-lowering drugs Their use has been associated with pigment changes of the iris and the eyelid Recently, these prostaglandin analogues have become popular for stimulating eyelash growth However, these should be used with caution by those with darker skin types and those with a history of melasma and other pigmentation disorders PGF2 was shown to increase tyrosinase activity, suggesting that prostaglandins may stimulate melanin formation89 Antioxidants can prevent the formation of prostaglandins,90 thereby preventing inflammation and tyrosinase activation Inflammation may also play a role in skin pigmentation through the effects of histamine Histamine is released from mast cells during inflammation and has been found to increase the level of tyrosinase-mediated cAMP via actions on protein kinase A (PKA) The release of histamine stimulates melanogenesis and results in the production of eumelanin rather than pheomelanin91 Thus, a possible approach to prevent postin-
flammatory hyperpigmentation and other pigmentation disorders might be to block histamine action Yoshida et al found that blocking H2 receptors with famotidine suppressed the increase in melanogenesis, but antagonists of H1 and H3 do not have any effect92 The effect of histamine-related agents is difficult to predict and their use to treat hypo- and hyperpigmentation is still unreliable However, antioxidants, especially flavonoids, have been shown to inhibit histamine release93 Antioxidants likely prevent inflammation and subsequent pigmentation by several other mechanisms including effects on transcription factor nuclear factor- B (NFB), inducible nitric oxide synthase expression, and inhibition of cyclooxygenase94 In spite of the many cited reasons to use antioxidants and free radical scavengers as hypopigmenting agents, the indiscriminate use of these compounds should be weighed with caution Each antioxidant and its effects should be considered separately and it should not be assumed that all antioxidants will inhibit melanogenesis In fact, an opposite effect seems to be possible in some cases and unexpected hyperpigmentation can occur For example, quercetin, an extract of onion, is a tyrosinase inhibitor in vitro95; however, this flavonol has been described as a strong inductor of melanogenesis in normal and malignant human melanocytes,96 and in reconstituted three-dimensional human epidermis models97 Glycyrrhizin, another popular antioxidant that is frequently used to inhibit tyrosinase, has been shown to stimulate melanogenesis in B16 melanoma cells98 Clinical trials of each individual antioxidant agent, and combinations of agents, are warranted before one can feel confident of their ability to inhibit melanogenesis
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