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    Chemistry

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    Also known as: 497-76-7, Arbutoside, Ursin, Uvasol, P-arbutin, Beta-arbutin
    Molecular Formula
    C12H16O7
    Molecular Weight
    272.25  g/mol
    InChI Key
    BJRNKVDFDLYUGJ-RMPHRYRLSA-N
    FDA UNII
    C5INA23HXF
    Arbutin
    -arbutin is a natural product found in Grevillea robusta, Halocarpus biformis, and other organisms with data available.
    1 2D Structure

    Arbutin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
    2.1.2 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
    2.1.3 InChI Key
    BJRNKVDFDLYUGJ-RMPHRYRLSA-N
    2.1.4 Canonical SMILES
    C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
    2.1.5 Isomeric SMILES
    C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    C5INA23HXF
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 497-76-7

    2. Arbutoside

    3. Ursin

    4. Uvasol

    5. P-arbutin

    6. Beta-arbutin

    7. 4-hydroxyphenyl Beta-d-glucopyranoside

    8. P-hydroxyphenyl Beta-d-glucoside

    9. 4-hydroxyphenyl-beta-d-glucopyranoside

    10. Arbutinum

    11. P-hydroxyphenyl Beta-d-glucopyranoside

    12. Ursi

    13. Hydroquinone-o-beta-d-glucopyranoside

    14. Hydroquinone Beta-d-glucopyranoside

    15. Ericolin

    16. Hydroquinone O-beta-d-glucopyranoside

    17. Hydroquinone-glucose

    18. Hydroquinone

    19. A-d-glucopyranoside

    20. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

    21. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2h-pyran-3,4,5-triol

    22. C5ina23hxf

    23. 4-hydroxyphenyl-.beta.-d-glucopyranoside

    24. Chembl232202

    25. Chebi:18305

    26. Hydroquinone Glucose

    27. Nsc-4036

    28. Arbutine

    29. Arbutyne

    30. Hydroquinone-beta-d-glucopyranoside

    31. Dsstox_cid_20152

    32. Dsstox_rid_79450

    33. Dsstox_gsid_40152

    34. Nsc 4036

    35. Mfcd00016915

    36. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol

    37. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-oxidanylphenoxy)oxane-3,4,5-triol

    38. Cas-497-76-7

    39. Sr-05000002157

    40. Unii-c5ina23hxf

    41. Ccris 9273

    42. B-arbutin

    43. Hsdb 7661

    44. Uva,p-arbutin

    45. Ncgc00095599-01

    46. Einecs 207-850-3

    47. Beta-d-glucopyranoside, 4-hydroxyphenyl

    48. Brn 0089673

    49. Spectrum_000786

    50. Specplus_000314

    51. Arbutin [hsdb]

    52. Arbutin [inci]

    53. Arbutin, >=98%

    54. Arbutin [mi]

    55. Arbutinum [hpus]

    56. Arbutin [mart.]

    57. Prestwick3_001026

    58. Spectrum2_000662

    59. Spectrum3_001233

    60. Spectrum4_001474

    61. Spectrum5_000147

    62. Arbutin [who-dd]

    63. Bmse000365

    64. Arbutin (uva, P-arbutin)

    65. Arbutin, Analytical Standard

    66. Schembl36351

    67. Arbutin - Uva - P-arbutin

    68. Bspbio_001211

    69. Bspbio_002706

    70. Hydroquinone-beta-d-glucoside

    71. Kbiogr_002047

    72. Kbioss_001266

    73. Spectrum300539

    74. 5-17-07-00110 (beilstein Handbook Reference)

    75. Mls002207046

    76. Divk1c_006410

    77. Spbio_000723

    78. Bpbio1_001333

    79. Megxp0_001504

    80. Dtxsid7040152

    81. Kbio1_001354

    82. Kbio2_001266

    83. Kbio2_003834

    84. Kbio2_006402

    85. Kbio3_002206

    86. Hydroquinone O--d-glucopyranoside

    87. Hms2098m13

    88. Hms3715m13

    89. P-hydroxyphenyl Beta -d-glucoside

    90. Zinc518554

    91. Hy-n0192

    92. 4-hydroxyphenyl-beta-glucopyranoside

    93. Hydroquinone Beta -d-glucopyranoside

    94. Tox21_111509

    95. Tox21_302428

    96. B-d-glucopyranoside, 4-hydroxyphenyl

    97. Bdbm50219502

    98. Ccg-38565

    99. S2263

    100. Akos015965305

    101. Tox21_111509_1

    102. Db11217

    103. Ks-5252

    104. Sdccgmls-0066538.p001

    105. P-hydroxyphenyl Beta -d-glucopyranoside

    106. Smp1_000028

    107. Ncgc00166076-02

    108. Ncgc00166076-03

    109. Ncgc00166076-04

    110. Ncgc00166076-07

    111. Ncgc00166076-09

    112. Ncgc00255705-01

    113. Ac-20183

    114. Beta -d-glucopyranoside, 4-hydroxyphenyl

    115. Beta-d-glucopyranoside, 4-hydroxyphenyl-

    116. I(2)-d-glucopyranoside, 4-hydroxyphenyl

    117. Smr001233417

    118. A0522

    119. Ab00443586

    120. Hydroquinone-.beta.-d-glucopyranoside

    121. N1714

    122. Sw199492-2

    123. C06186

    124. 4-hydroxyphenyl B-d-glucopyranoside, 9ci, 8ci

    125. 497a767

    126. A827849

    127. Arbutin, Primary Pharmaceutical Reference Standard

    128. Q416446

    129. Sr-05000002157-2

    130. Sr-05000002157-4

    131. Alpha-arbutin; 4-hydroquinone-alpha-d-glucopyranoside

    132. Arbutin, European Pharmacopoeia (ep) Reference Standard

    133. 4e19b706-2013-4401-a1fc-a154dadf42b4

    134. (2s,3r,4s,5s,6r)-2-(4-hydroxyphenoxy)-6-methylol-tetrahydropyran-3,4,5-triol

    135. 7oq

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 272.25 g/mol
    Molecular Formula C12H16O7
    XLogP3-0.7
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count3
    Exact Mass272.08960285 g/mol
    Monoisotopic Mass272.08960285 g/mol
    Topological Polar Surface Area120 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity279
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    /EXPL THER/ Although the toxicogenomics of A375 human malignant melanoma cells treated with arbutin have been elucidated using DNA microarray, the proteomics of the cellular response to this compound are still poorly understood. ...This study ... performed proteomic analyses to investigate the anticancer effect of arbutin on the protein expression profile in A375 cells. After treatment with arbutin (8 ug/mL) for 24, 48 and 72 hr, the proteomic profiles of control and arbutin-treated A375 cells were compared, and 26 differentially expressed proteins (7 upregulated and 19 downregulated proteins) were identified by MALDI-Q-TOF MS and MS/MS. Among these proteins, 13 isoforms of six identical proteins were observed. Bioinformatic tools were used to search for protein function and to predict protein interactions. The interaction network of 14 differentially expressed proteins was found to be correlated with the downstream regulation of p53 tumor suppressor and cell apoptosis. In addition, three upregulated proteins (14-3-3G, VDAC-1 and p53) and five downregulated proteins (ENPL, ENOA, IMDH2, PRDX1 and VIME) in arbutin-treated A375 cells were validated by RT-PCR analysis. These proteins were found to play important roles in the suppression of cancer development.

    PMID:18996230 Nawarak J et al; Biochim Biophys Acta Oct 18 (Epub ahead of print) (2008)

    4.2 Drug Indication

    Indicated for over-the-counter use for epidermal hyperpigmentation in various skin conditions, such as melasma, freckles, and senile lentigines.

    5 Pharmacology and Biochemistry
    5.1 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. -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 -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.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Arbutin was found to be extensively absorbed from the gastrointestinal tract where it is primarily converted to hydroquinone.

    Route of Elimination

    During the first 4 hours following ingestion of a single dose of 210 mg arbutin in healthy volunteers, 224.5 mol/L hydroquinone glucuronide and 182 mol/L of hydroquinone sulfate were recovered in the urine.

    Volume of Distribution

    No pharmacokinetic data available.

    Clearance

    No pharmacokinetic data available.

    The urinary excretion of arbutin metabolites was examined in a randomized crossover design in 16 healthy volunteers after the application of a single oral dose of bearberry leaves dry extract (BLDE). There were two groups of application using either film-coated tablets (FCT) or aqueous solution (AS). The urine sample analysis was performed by a validated HPLC coolarray method (hydroquinone) and a validated capillary electrophoresis method (hydroquinone-glucuronide, hydroquinone-sulfate). The total amounts of hydroquinone equivalents excreted in the urine from BLDE were similar in both groups. With FCT, 64.8% of the arbutin dose administered was excreted; with AS, 66.7% was excreted (p = 0.61). The maximum mean urinary concentration of hydroquinone equivalents was a little higher and peaked earlier in the AS group versus the FCT group, although this did not reach statistical significance (Cur max = 1.6893 umol/mL vs. 1.1250 umol/mL, p = 0.13; tmax (t midpoint) = 3.60 h vs. 4.40 hr, p = 0.38). The relative bioavailability of FCT compared to AS was 103.3% for total hydroquinone equivalents. There was substantial intersubject variability. No significant differences between the two groups were found in the metabolite patterns detected (hydroquinone, hydroquinone-glucuronide, and hydroquinone-sulfate).

    PMID:12162475 Schindler G et al; J Clin Pharmacol 42 (8): 920-7 (2002)

    To study the effects of aloesin and arbutin on normal cultured human melanocytes in synergetic method. Building up the system of cultured human melanocytes. The cultured melanocytes in vitro were treated with the mixture of aloesin and arbutin. The cell viability and tyrosinase activity was measured by MTT assay, utilization of L-Dopa as the substrate respectively; melanin content was measured by image analysis system. Furthermore, the effects of the mixture on melanocytes were compared with that of aloesin and arbutin. The mixture of aloesin and arbutin showed an inhibition on tyrosinase activity of human melanocytes and reduced significantly melanin content. Between the mixture and the single use of aloesin or arbutin, there is significant difference (P<0.05). On the other hand, the mixture has little influence on melanocytes viability and there is negative significance. The mixture of aloesin and arbutin can significantly inhibit the tyrosinase activity and melanogenesis of cultured human melanocytes. It showed the effects of aloesin and arbutin in a synergistic manner.

    PMID:15623110 Yang ZQ et al; Zhonghua Zheng Xing Wai Ke Za Zhi 20 (5): 369-71 (2004)

    5.3 Metabolism/Metabolites

    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.

    5.4 Biological Half-Life

    No pharmacokinetic data available.

    5.5 Mechanism of Action

    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 study ... presents evidence that cotreatment of aloesin and arbutin inhibits tyrosinase activity in a synergistic manner by acting through a different action mechanism. Aloesin or arbutin similarly inhibited enzyme activity of human- and mushroom-tyrosinases with an IC50 value of 0.1 or 0.04 mM, respectively. Lineweaver-Burk plots of the enzyme kinetics data showed that aloesin inhibited tyrosinase activity noncompetitively with a Ki value of 5.3 mM, whereas arbutin did it competitively (Maeda, 1996). We then examined whether cotreatment of these agents inhibits the tyrosinase activity in a synergistic manner. The results showed that 0.01 mM aloesin in the presence of 0.03 mM arbutin inhibited activity of mushroom by 80% of the control value and the reverse was also true. The inhibitory effects were calculated to be synergistic according to the Burgi method. Taken together, we suggest that aloesin along with arbutin inhibits in synergy melanin production by combined mechanisms of noncompetitive and competitive inhibitions of tyrosinase activity.

    PMID:10403123 Jin YH et al; Arch Pharm Res 22 (3): 232-6 (1999)

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    API | Excipient name

    Arbutin

    Synonyms

    497-76-7, Arbutoside, Ursin, Uvasol, P-arbutin, Beta-arbutin

    Cas Number

    497-76-7

    Unique Ingredient Identifier (UNII)

    C5INA23HXF

    About Arbutin

    -arbutin is a natural product found in Grevillea robusta, Halocarpus biformis, and other organisms with data available.

    Arbutin Manufacturers

    A Arbutin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Arbutin, including repackagers and relabelers. The FDA regulates Arbutin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Arbutin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Arbutin manufacturers with USDMF, JDMF, KDMF, CEP, GMP, and COA related information on PhamaCompass.

    Arbutin Suppliers

    A Arbutin supplier is an individual or a company that provides Arbutin active pharmaceutical ingredient (API) or Arbutin finished formulations upon request. The Arbutin suppliers may include Arbutin API manufacturers, exporters, distributors and traders.

    click here to find a list of Arbutin suppliers with USDMF, JDMF, KDMF, CEP, GMP, and COA related information on PharmaCompass.

    Arbutin GMP

    Arbutin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Arbutin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, and more, enabling you to easily find the right Arbutin GMP manufacturer or Arbutin GMP API supplier for your needs.

    Arbutin CoA

    A Arbutin CoA (Certificate of Analysis) is a formal document that attests to Arbutin's compliance with Arbutin specifications and serves as a tool for batch-level quality control.

    Arbutin CoA mostly includes findings from lab analyses of a specific batch. For each Arbutin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Arbutin may be tested according to a variety of international standards, such as European Pharmacopoeia (Arbutin EP), Arbutin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Arbutin USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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