Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Arbutin
- DrugBank Accession Number
- DB11217
- Background
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 Hydroquinone. It is found in foods, over-the-counter drugs, and herbal dietary supplements 6. 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 1. It has also been used as an anti-infective for the urinary system as well as a diuretic 6. Arbutin is available in both natural and synthetic forms; it can be synthesized from acetobromglucose and Hydroquinone 6. Arbutin is a competitive inhibitor of tyrosinase (E.C.1.14.18.1) in melanocytes 1, 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 Hydroquinone 5.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Arbutin (DB11217)
- Weight
- Average: 272.2512
Monoisotopic: 272.089602866 - Chemical Formula
- C12H16O7
- 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
Pharmacology
- Indication
Indicated for over-the-counter use for epidermal hyperpigmentation in various skin conditions, such as melasma, freckles, and senile lentigines.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Mild lower urinary tract infection •••••••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
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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.
- Mechanism of action
Arbutin is a hydroquinone glycoside, however the hydroquinone moiety is not solely responsible for the de-pigmentating actions of arbutin 5. 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 1. 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 1. 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 2. The contradictory findings across studies may be due to previous studies using terminally-differentiated melanocytes and melanoma cells 2.
Target Actions Organism ATyrosinase inhibitorHumans - Absorption
Arbutin was found to be extensively absorbed from the gastrointestinal tract where it is primarily converted to hydroquinone 6.
- Volume of distribution
No pharmacokinetic data available.
- Protein binding
No pharmacokinetic data available.
- Metabolism
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 6. Hydroquinone is further metabolized into the main metabolites, hydroquinone glucuronide and hydroquinone sulfate 6.
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- Route of elimination
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 6.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
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In an acute oral toxicity study, the LD50-value for β-arbutin is 9804 mg/kg bw for the mouse and 8715 mg/kg bw for the rat 7. Dermal LD50 value in rat and mouse was reported to be greater than 928 mg/kg bw, according to an acute dermal toxicity study 7. Extremely high doses may cause ringing in the ears, shortness of breath, convulsions, collapse, vomiting and delirium 6. Nausea and vomiting were seen individuals with sensitive stomachs following oral ingestion of 15 g of dried uva ursi leaves that contain arbutin 6.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Ursin / Uvasol
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image AHC Phyto Complex Gel Ampoule Liquid 0.6 g/30mL Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US 
Dr Young 2p Brightening UV Sun Block SPF50 PA Cream 0.5 mL/50mL Topical The Doctor's Cosmetic Inc 2009-11-01 Not applicable US Elcure C White Serum Liquid 2 g/100mL Topical Elcure Co., Ltd. 2016-03-30 2017-04-20 US Hydro H Solution 2.5 mg/1mL Topical General Bio Co., Ltd. 2014-12-09 Not applicable US IASO White Science EX Cream 0.02 g/1g Topical Iaso Inc 2011-01-17 2018-03-12 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Abalone Crystaldouble EX Ampoule Arbutin (2.2 g/100mL) + Adenosine (0.044 g/100mL) Liquid Topical C&bcosmetic Co.,ltd. 2017-03-10 Not applicable US Absolute Total BB SPF37 PA 3Plus Arbutin (0.8 g/40g) + Adenosine (0.016 g/40g) + Titanium dioxide (3.6 g/40g) + Zinc oxide (2.52 g/40g) Cream Topical Wizcoz Corporation Ltd 2011-12-01 Not applicable US AHC Premium Intense Contour Balm Arbutin (1 g/50mL) + Adenosine (0.02 g/50mL) + Aluminium tristearate (0.04 g/50mL) + Aluminum hydroxide (0.45 g/50mL) + Methicone (20 CST) (1.3 g/50mL) + Octinoxate (1.5 g/50mL) + Talc (2.05 g/50mL) + Titanium dioxide (3.96 g/50mL) + Zinc oxide (0.96 g/50mL) Cream Topical Carver Korea Co.,Ltd. 2014-01-15 2017-11-22 US AHC Vital Complex C-15 Ampoule Arbutin (0.6 g/30mL) + Adenosine (12 mg/30mL) Liquid Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US Cathycat Chewy CREAM FOUNDATION SPF23 PA WHITENING ANTI WRINKLE 21 Arbutin (2 g/100g) + Hydroxyproline (0.5 g/100g) + Octinoxate (1.5 g/100g) + Titanium dioxide (8.2062 g/100g) Liquid Topical Lg Household & Health Care Ltd. 2011-04-15 2012-04-15 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Abalone Crystaldouble EX Ampoule Arbutin (2.2 g/100mL) + Adenosine (0.044 g/100mL) Liquid Topical C&bcosmetic Co.,ltd. 2017-03-10 Not applicable US AHC Phyto Complex Gel Ampoule Arbutin (0.6 g/30mL) Liquid Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US AHC Premium Intense Contour Balm Arbutin (1 g/50mL) + Adenosine (0.02 g/50mL) + Aluminium tristearate (0.04 g/50mL) + Aluminum hydroxide (0.45 g/50mL) + Methicone (20 CST) (1.3 g/50mL) + Octinoxate (1.5 g/50mL) + Talc (2.05 g/50mL) + Titanium dioxide (3.96 g/50mL) + Zinc oxide (0.96 g/50mL) Cream Topical Carver Korea Co.,Ltd. 2014-01-15 2017-11-22 US AHC Vital Complex C-15 Ampoule Arbutin (0.6 g/30mL) + Adenosine (12 mg/30mL) Liquid Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US Cellbn Damage Anti-aging Eye Reviver Arbutin (2 g/100mL) + Adenosine (0.05 g/100mL) Cream Topical Worldcostec.co.,ltd 2017-05-26 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound 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.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Phenolic glycosides
- Alternative Parents
- Hexoses / O-glycosyl compounds / 4-alkoxyphenols / Phenoxy compounds / Phenol ethers / 1-hydroxy-2-unsubstituted benzenoids / Oxanes / Secondary alcohols / Polyols / Oxacyclic compounds show 3 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 4-alkoxyphenol / Acetal / Alcohol / Aromatic heteromonocyclic compound / Benzenoid / Hexose monosaccharide / Hydrocarbon derivative / Monocyclic benzene moiety / Monosaccharide show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- beta-D-glucoside, monosaccharide derivative (CHEBI:18305)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- C5INA23HXF
- CAS number
- 497-76-7
- InChI Key
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N
- InChI
- InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
- IUPAC Name
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
- SMILES
- OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
References
- General References
- Maeda K, Fukuda M: Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther. 1996 Feb;276(2):765-9. [Article]
- Inoue Y, Hasegawa S, Yamada T, Date Y, Mizutani H, Nakata S, Matsunaga K, Akamatsu H: Analysis of the effects of hydroquinone and arbutin on the differentiation of melanocytes. Biol Pharm Bull. 2013;36(11):1722-30. [Article]
- Sugimoto K, Nishimura T, Nomura K, Sugimoto K, Kuriki T: Inhibitory effects of alpha-arbutin on melanin synthesis in cultured human melanoma cells and a three-dimensional human skin model. Biol Pharm Bull. 2004 Apr;27(4):510-4. [Article]
- Lim YJ, Lee EH, Kang TH, Ha SK, Oh MS, Kim SM, Yoon TJ, Kang C, Park JH, Kim SY: Inhibitory effects of arbutin on melanin biosynthesis of alpha-melanocyte stimulating hormone-induced hyperpigmentation in cultured brownish guinea pig skin tissues. Arch Pharm Res. 2009 Mar;32(3):367-73. doi: 10.1007/s12272-009-1309-8. Epub 2009 Apr 23. [Article]
- Chakraborty AK, Funasaka Y, Komoto M, Ichihashi M: Effect of arbutin on melanogenic proteins in human melanocytes. Pigment Cell Res. 1998 Aug;11(4):206-12. [Article]
- Chemical Information Review Document for Arbutin [CAS No. 497-76-7] for Arbutin and Extracts from Arctostaphylos uva-ursi [File]
- European Commission Scientific Committee on Consumer Products (SCCP): Opinion on beta-arbutin [File]
- External Links
- PDB Entries
- 7vl6
- MSDS
- Download (47.3 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2, 3 Suspended Treatment Melasma 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical 0.6 g/30mL Gel Topical Cream Cutaneous Cream Topical Cream Topical 0.5 mL/50mL Liquid Topical 2 g/100mL Solution Topical 2.5 mg/1mL Cream Topical 0.02 g/1g Cream Topical 0.02 g/1mL Ointment Cutaneous; Infiltration 1.2 g/5mL Liquid Cutaneous; Infiltration 0.36 g/5g Lotion Cutaneous; Infiltration 0.36 g/5mL Lotion Topical 2.1 g/100g Liquid Cutaneous Aerosol, spray Topical Cream Topical 4.03 mg/57g Cream Topical 4.02 mg/57g Powder Topical Tablet, film coated Oral Spray Topical Emulsion Topical 2.1 mL/100mL Cream Topical 2.1 mL/100mL Liquid Topical Emulsion Topical Liquid Topical 1 mg/150mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 197 MSDS water solubility ≥ 10g/100g European Commission Scientific Committee on Consumer Products (SCCP): Opinion on beta-arbutin logP 1.35 European Commission Scientific Committee on Consumer Products (SCCP): Opinion on beta-arbutin - Predicted Properties
Property Value Source Water Solubility 39.1 mg/mL ALOGPS logP -1.4 ALOGPS logP -0.9 Chemaxon logS -0.84 ALOGPS pKa (Strongest Acidic) 9.82 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 119.61 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 62.16 m3·mol-1 Chemaxon Polarizability 25.88 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.4432922 predictedDarkChem Lite v0.1.0 [M-H]- 162.7824929 predictedDarkChem Lite v0.1.0 [M-H]- 165.0710929 predictedDarkChem Lite v0.1.0 [M-H]- 160.11905 predictedDeepCCS 1.0 (2019) [M+H]+ 161.206381 predictedDarkChem Lite v0.1.0 [M+H]+ 163.1514929 predictedDarkChem Lite v0.1.0 [M+H]+ 163.0960929 predictedDarkChem Lite v0.1.0 [M+H]+ 162.26637 predictedDeepCCS 1.0 (2019) [M+Na]+ 168.1287855 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.8564929 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.29051 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine (By similarity). In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone (PubMed:28661582)
- Specific Function
- Copper ion binding
- Gene Name
- TYR
- Uniprot ID
- P14679
- Uniprot Name
- Tyrosinase
- Molecular Weight
- 60392.69 Da
References
- Maeda K, Fukuda M: Arbutin: mechanism of its depigmenting action in human melanocyte culture. J Pharmacol Exp Ther. 1996 Feb;276(2):765-9. [Article]
- Chakraborty AK, Funasaka Y, Komoto M, Ichihashi M: Effect of arbutin on melanogenic proteins in human melanocytes. Pigment Cell Res. 1998 Aug;11(4):206-12. [Article]
- Im KH, Baek SA, Choi J, Lee TS: Antioxidant, Anti-Melanogenic and Anti-Wrinkle Effects of Phellinus vaninii. Mycobiology. 2019 Oct 15;47(4):494-505. doi: 10.1080/12298093.2019.1673595. eCollection 2019. [Article]
- Lu H, Yang K, Zhan L, Lu T, Chen X, Cai X, Zhou C, Li H, Qian L, Lv G, Chen S: Optimization of Flavonoid Extraction in Dendrobium officinale Leaves and Their Inhibitory Effects on Tyrosinase Activity. Int J Anal Chem. 2019 Mar 13;2019:7849198. doi: 10.1155/2019/7849198. eCollection 2019. [Article]
- Ghaffarzadeh J, Nasuhi Pur F: Calixarbutin: A Novel Calixarene-based Potential Water-soluble Anti-tyrosinase Agent with High Anti-melanoma Activity. Iran J Pharm Res. 2020 Spring;19(2):236-241. doi: 10.22037/ijpr.2020.112506.13798. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- Antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes]. Yakugaku Zasshi. 1996 Aug;116(8):630-8. [Article]
Drug created at December 03, 2015 16:51 / Updated at January 07, 2021 03:13