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Alpha Arbutin  

OVERVIEW
History and Significance
Applications

CHEMISTRY
General Manufacturing Process
Available Formulations
Biologic Activity

APPROVED INDICATIONS AND THERAPEUTIC USE
Hyperpigmentation
Lentigines
Melasma and Chloasma
Freckles

CLINICAL CONSIDERATIONS
Patient Instructions
Duration and Frequency of Treatment
Contraindications, Warnings, Precautions

PRODUCT SELECTION FOR RESULTS

REFERENCES

Alpha Arbutin  

 OVERVIEW

Arbutin is a glucosulated hydroquinone, extracted from the bearberry plant. Hydroquinone has been commercially available since the 1960s as an agent in skin lightening products.1 Arbutin is naturally found in wheat, pear skins, and the leaves of blueberries and cranberries, and it is metabolized by the body to produce hydroquinone with most of the product excreted in urine. Topical application of arbutin inhibits the production of melanin with minimal systemic absorption.

 History and Significance

Arbutin is the active ingredient extracted from the leaves of the bearberry (Arctostaphylos uva-ursi) plant. Historically, the extracts were used as a diuretic and to treat urinary tract infections, cystitis, and kidney stones.2 Arbutin is converted in the body to hydroquinone, a phenolic agent with antimicrobial, astringent, and disinfectant properties.2 Topical hydroquinone is a common treatment for hyperpigmentation. Arbutin is a glycolylated benzoquinone considered to be a non-phenolic agent, also effective in hyperpigmentation conditions because it converts to hydroquinone.2,3 In 1990, the toxicity of hydroquinone prompted extracts of uva-ursi to be banned from nonprescription oral remedies in diet and menstrual/diuretic products.

 Applications

Arbutin is used as a stabilizer for color photographs, diuretics, anti-infectives for the urinary system, and as a skin-lightening agent. Arbutin has similar effects as hydroquinone, inhibiting melanin formation.

 CHEMISTRY

Chemical name: Arbutin, arbutoside or hydroquinone beta-D-glucopyranoside

Molecular formula: Glucosulated hydroquinone (both ether and glycoside) which is hydrolyzed to hydroquinone.

Molecular formula: C12H16O7



Arbutin is a white crystalline powder that is water soluble, added to supplements or formulations. Arbutin is available as a crushed leaf or powder from the uva-ursi plant in herbal remedies, such as teas and capsules.3 Arbutin can also be commercially synthesized from acetobromglucose and hydroquinone, or from the reaction of beta-D-glucose pentaacetate and hydroquinonemonobenzyl ether in the presence of phosphorus oxychloride.3

 General Manufacturing Process

Bearberry extract from Arctostaphylos uva-ursi is combined with a reducing agent to help inhibit the oxidation reactions leading to the formation of melanin from tyrosine. Other tyrosinase inhibitors, such as orange extract, lemon extract, and cucumber extract, along with complementary ingredients, such as glycolic acid, lactic acid, and sodium hyaluronate, may be added to the formulation to augment the lightening effect.

 Available Formulations

Arbutin is included in skin lightening creams and serums. Other agents such as retinol or alpha hydroxy acids can be added to enhance penetration of arbutin to dermal layers.3

 Biologic Activity

Systemically, arbutin is absorbed in the gastrointestinal tract and converted to bioavailable hydroquinone. 65%-75% of ingested arbutin is renally cleared. Hydroquinone inhibits the enzyme tyrosinase, thereby affecting melanin production by reducing DOPA conversion to melanin.2 Enzyme inhibition supports degradation of melanosomes and melanocytes. Topical application of arbutin provides a localized effect of hydroquinone with less toxicity and irritation, even at higher concentrations. Studies have shown that arbutin produces a dose-dependent reduction in tyrosinase activity and melanin content in melanocytes.3,4

 APPROVED INDICATIONS AND THERAPEUTIC USE

APPROVED INDICATIONS
Hyperpigmentation
Lentigines
Melasma and Chloasma
Freckles
Arbutin is water-soluble and hydrolyzed to hydroquinone. Topical formulations containing arbutin provide hydroquinone locally.

 Hyperpigmentation

Arbutin has been used for postinflammatory hyperpigmentation and it has been used effectively to treat hyperpigmentation characterized by hyperactive melanocytes.3 Continued use of the products maintain a reduction of melanin concentration, particularly in areas exposed to the sun.

 Lentigines

Lentigines are characterized by uneven pigmentation of the skin, also known as persistent liver spots, age spots, or sun spots. Topical application of arbutin supports the degradation of melanin content that has accumulated over time.5

 Melasma and Chloasma

Melasma is facial hyperpigmentation that is often manifested among pregnant women due to wide shifts in hormones. In clinical studies, patients exhibited a significant decrease in pigment density when treated with topical arbutin gel.(6) Topical application of arbutin is considered a safer, less irritating alternative to hydroquinone, with similar effects and minimal systemic absorption.5

 Freckles

Freckles are clusters of concentrated melanin, predominant among fair-skinned individuals. Formation and color intensity can be triggered by UVB exposure, which stimulates melanin production by melanocytes. Arbutin serves to inhibit melanocyte activity and support the degradation of melanin content in the keratogenous layer.

 CLINICAL CONSIDERATIONS

The mechanism of action of arbutin to inhibit melanin production is comparable to hydroquinone, with less toxicity and irritation. Arbutin is considered a non-phenol, safer alternative to topical hydroquinone and penetration can be enhanced when combined with other dermatologic agents. KAVI Advanced Melanin Repair Serum combines a 1% concentration of alpha arbutin with 8% glycolic acid and hyaluronic acid in a botanical base, ingredients that enhance dermal penetration and moisturization and support tissue repair.

 Patient Instructions; Duration and Frequency of Treatment

Apply a thin layer of the Advanced Melanin Repair Serum on the target area after cleansing to correct pigmentation variance.
Frequency: Safe to apply twice daily.

 Contraindications, Warnings, Precautions

For external use only. Use as directed by your healthcare professional. Use with caution under supervision of a healthcare professional in children and pregnant women. Avoid application to irritated or open wounds. Use sunblock on areas exposed to the sun.

 PRODUCT SELECTION FOR RESULTS

Arbutin is a safer, non-phenol option with a proven target of activity for the healthcare professional's treatment plan. The KAVI Melanin Repair Serum combines the benefits of alpha hydroxy acid and hyaluronic acid with alpha arbutin to promote even skin color, texture, and tone. As part of a treatment plan employing KAVI products, the Advanced Melanin Repair Serum is formulated to complement both treatment and maintenance cycles.

Additional information on the Advanced Melanin Repair Serum

 REFERENCES

1. O'Donoghue JL. "Hydroquinone and its Analogues in Dermatology - A Risk-Benefit Viewpoint", J Cos Derm. 2006; 5(3):196-203.
2. "Chemical Information Review Document for Arbutin and Extracts from Arctostaphylos uva-ursi", National Toxicology Program. January 2006.
3. Halder RM, Richards GM. "Topical Agents Used in the Management of Hyperpigmentation", Skin Therapy Lett. Jun-Jul, 2004; 9(6):1-3. Review.
4. Tokiwa Y, Kitagawa M, Raku T, et al. "Enzymatic Synthesis of Arbutin Undecylenic Acid Ester and its Inhibitory Effect on Melanin Synthesis", Bioorganic and Medicinal Chemistry Letters. Vol 17(11), Jun, 2007, pp. 3105-3108.
5. Draelos ZD. "Skin Lightening Preparations and the Hydroquinone Controversy", Dermatol Ther. Sep-Oct, 2007; 20(5):308-13. Review.
6. Ertam I, Mutlu B, Unal I, et al. "Efficiency of Ellagic Acid and Arbutin in Melasma: A Randomized, Prospective, Open-Label Study", J Dermatol. Sep, 2008; 35(9):570-4.

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