Repositioning Candidate Details
| Candidate ID: | R1352 |
| Source ID: | DB11217 |
| Source Type: | approved |
| Compound Type: | small molecule |
| Compound Name: | Arbutin |
| Synonyms: | 4-Hydroxyphenyl-beta-D-glucopyranoside; beta-Arbutin; hydroquinone O-β-D-glucopyranoside; Hydroquinone-O-beta-D-glucopyranoside; p-hydroxyphenyl β-D-glucopyranoside; p-hydroxyphenyl β-D-glucoside |
| Molecular Formula: | C12H16O7 |
| SMILES: | OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O |
| Structure: |
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| DrugBank Description: | 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 . |
| CAS Number: | 497-76-7 |
| Molecular Weight: | 272.2512 |
| DrugBank Indication: | Indicated for over-the-counter use for epidermal hyperpigmentation in various skin conditions, such as melasma, freckles, and senile lentigines. |
| DrugBank Pharmacology: | 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 . |
| DrugBank MoA: | 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 . |
| Targets: | Tyrosinase inhibitor |
| Inclusion Criteria: | Therapeutic strategy associated |
