DrugBank ID:

DB11217

Description:

Extracted from the dried leaves of bearberry plant in the genusArctostaphylosand other plants commonly in theEricaceaefamily, arbutin is a beta-D-glucopyranoside ofHydroquinone. 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 andHydroquinone. 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 observedin vitro. Arbutin was shown to be less cytotoxic to melanocytes in culture compared toHydroquinone. [DrugBank]

Targets:

Tyrosinase (Humans) [DrugBank]

Pharmacodynamics:

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 1. α-Arbutin produced a concentration-dependent inhibition of melanin synthesis of human melanoma cells, HMV-II 3. 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 3. The addition of arbutin blocked and inhibited α-MSH-stimulated melanogenesis in B16 melanoma cells, brownish guinea pig, and human skin tissue 4. 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 6. In mouse skin, arbutin counteracted oxidative stress induced by 12-O-tetradecanoylphorbol-13-acetate 6. [DrugBank]

SMILES:

OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O

2D structures:  

3D structures: