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General Description:

Arbutin, identified by CAS number 497-76-7, is a notable compound with significant therapeutic applications. Extracted from the dried leaves of bearberry plant in the genus _Arctostaphylos_ and other plants commonly in the _Ericaceae_ family, arbutin is a beta-D-glucopyranoside of . It is found in foods, over-the-counter drugs, and herbal dietary supplements . Most commonly, it is an active ingredient in skincare and cosmetic products as a skin-lightening agent for the prevention of melanin formation in various skin conditions that involve cutaneous hyperpigmentation or hyperactive melanocyte function . It has also been used as an anti-infective for the urinary system as well as a diuretic . Arbutin is available in both natural and synthetic forms; it can be synthesized from acetobromglucose and . Arbutin is a competitive inhibitor of tyrosinase (E.C.1.14.18.1) in melanocytes , and the inhibition of melanin synthesis at non-toxic concentrations was observed _in vitro_. Arbutin was shown to be less cytotoxic to melanocytes in culture compared to .

Indications:

This drug is primarily indicated for: Indicated for over-the-counter use for epidermal hyperpigmentation in various skin conditions, such as melasma, freckles, and senile lentigines. Its use in specific medical scenarios underscores its importance in the therapeutic landscape.

Metabolism:

Arbutin undergoes metabolic processing primarily in: Arbutin is readily susceptible to hydrolysis in dilute acids to yield D-glucose and hydroquinone. It is expected that orally administered arbutin is easily hydrolyzed to free hydroquinone molecules by stomach acid . Hydroquinone is further metabolized into the main metabolites, hydroquinone glucuronide and hydroquinone sulfate . This metabolic pathway ensures efficient processing of the drug, helping to minimize potential toxicity and side effects.

Absorption:

The absorption characteristics of Arbutin are crucial for its therapeutic efficacy: Arbutin was found to be extensively absorbed from the gastrointestinal tract where it is primarily converted to hydroquinone . The drug's ability to rapidly penetrate into cells ensures quick onset of action.

Half-life:

The half-life of Arbutin is an important consideration for its dosing schedule: No pharmacokinetic data available. This determines the duration of action and helps in formulating effective dosing regimens.

Protein Binding:

Arbutin exhibits a strong affinity for binding with plasma proteins: No pharmacokinetic data available. This property plays a key role in the drug's pharmacokinetics and distribution within the body.

Route of Elimination:

The elimination of Arbutin from the body primarily occurs through: During the first 4 hours following ingestion of a single dose of 210 mg arbutin in healthy volunteers, 224.5 μmol/L hydroquinone glucuronide and 182 μmol/L of hydroquinone sulfate were recovered in the urine . Understanding this pathway is essential for assessing potential drug accumulation and toxicity risks.

Volume of Distribution:

Arbutin is distributed throughout the body with a volume of distribution of: No pharmacokinetic data available. This metric indicates how extensively the drug permeates into body tissues.

Clearance:

The clearance rate of Arbutin is a critical factor in determining its safe and effective dosage: No pharmacokinetic data available. It reflects the efficiency with which the drug is removed from the systemic circulation.

Pharmacodynamics:

Arbutin exerts its therapeutic effects through: At non-toxic concentrations, arbutin inhibited the activity of tyrosinase in cultured human keratinocytes, while having minimal effect on the expression of tyrosinase mRNA or the synthesis of the enzyme . α-Arbutin produced a concentration-dependent inhibition of melanin synthesis of human melanoma cells, HMV-II . No inhibitory effect on HMV-II cell growth was seen at concentrations lower than 1.0 mM. At concentrations of 0.5 mM of arbutin, tyrosinase activity was reduced to 60% of that in non-treated cells . The addition of arbutin blocked and inhibited α-MSH-stimulated melanogenesis in B16 melanoma cells, brownish guinea pig, and human skin tissue . In a pilot study of healthy male adults exposed to UV B irradiation, topical administration of arbutin inhibited UV-induced nuclear factor-kappaB activation in human keratinocytes . In mouse skin, arbutin counteracted oxidative stress induced by 12-O-tetradecanoylphorbol-13-acetate . The drug's ability to modulate various physiological processes underscores its efficacy in treating specific conditions.

Mechanism of Action:

Arbutin functions by: Arbutin is a hydroquinone glycoside, however the hydroquinone moiety is not solely responsible for the de-pigmentating actions of arbutin . It acts as a competitive inhibitor of tyrosinase enzyme by acting on the L-tyrosine binding site to suppress melanogenesis and mediate its de-pigmenting actions on human skin . Tyrosinase is an enzyme involved in the regulation of rate-limiting steps during the synthesis of melanin; it regulates the conversion of L-tyrosine into L-dopa, and subsequent conversion of L-dopa to L-dopaquinone . Via inhibition of tyrosinase activity in a concentration-dependent manner, arbutin attenuates the production of melanin in melanocytes. While most studies suggest that arbutin has negligible effect on the tyrosinase mRNA expression, a study assessing the effect of arbutin on melanocyte differentiation inducement system using ES cells propose that arbutin may also downregulate the expression of tyrosinase in addition to its inhibitory action on the enzyme . The contradictory findings across studies may be due to previous studies using terminally-differentiated melanocytes and melanoma cells . This mechanism highlights the drug's role in inhibiting or promoting specific biological pathways, contributing to its therapeutic effects.

Toxicity:

Classification:

Arbutin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose, classified under the direct parent group Phenolic glycosides. This compound is a part of the Organic compounds, falling under the Organic oxygen compounds superclass, and categorized within the Organooxygen compounds class, specifically within the Carbohydrates and carbohydrate conjugates subclass.

Categories:

Arbutin is categorized under the following therapeutic classes: Carbohydrates, Glucosides, Glycosides. These classifications highlight the drug's diverse therapeutic applications and its importance in treating various conditions.

Experimental Properties:

Further physical and chemical characteristics of Arbutin include:

• Water Solubility: ≥ 10g/100g
• Melting Point: 197
• logP: 1.35