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    Chemistry

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    Also known as: Dithranol, 1143-38-0, 1,8-dihydroxyanthrone, Cignolin, 1,8-dihydroxy-9-anthrone, 1,8-dihydroxyanthracen-9(10h)-one
    Molecular Formula
    C14H10O3
    Molecular Weight
    226.23  g/mol
    InChI Key
    NUZWLKWWNNJHPT-UHFFFAOYSA-N
    FDA UNII
    U8CJK0JH5M
    Dithranol
    An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.
    1 2D Structure

    Dithranol

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1,8-dihydroxy-10H-anthracen-9-one
    2.1.2 InChI
    InChI=1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2
    2.1.3 InChI Key
    NUZWLKWWNNJHPT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1C2=C(C(=CC=C2)O)C(=O)C3=C1C=CC=C3O
    2.2 Other Identifiers
    2.2.1 UNII
    U8CJK0JH5M
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1,8 Dihydroxy 9 Anthrone

    2. 1,8,9-anthracenetriol

    3. 1,8-dihydroxy-9(10h)-anthracenone

    4. 1,8-dihydroxy-9-anthrone

    5. Anthraforte

    6. Anthranol

    7. Cignolin

    8. Cygnoline

    9. Dihydroxyanthranol

    10. Dithranol

    11. Dithrocream

    12. Ditranol Fna

    13. Fna, Ditranol

    14. Lasan

    15. Micanol

    16. Psoradrate

    17. Psoricrme

    2.3.2 Depositor-Supplied Synonyms

    1. Dithranol

    2. 1143-38-0

    3. 1,8-dihydroxyanthrone

    4. Cignolin

    5. 1,8-dihydroxy-9-anthrone

    6. 1,8-dihydroxyanthracen-9(10h)-one

    7. Chrysodermol

    8. Cigthranol

    9. 9(10h)-anthracenone, 1,8-dihydroxy-

    10. Batridol

    11. Psoriacid-stift

    12. Lasan

    13. Anthra-derm

    14. 1,8-dihydroxy-10h-anthracen-9-one

    15. Drithoscalp

    16. Derobin

    17. Drithocreme

    18. Batidrol

    19. Psodadrate

    20. Psoriacide

    21. Anthrone, 1,8-dihydroxy-

    22. 1,8-dihydroxy-9(10h)-anthracenone

    23. Nsc 43970

    24. Anthraderm

    25. Anthraline

    26. Nsc 629313

    27. Anthralin [usp]

    28. Dithranol [inn]

    29. Anthralin (dithranol)

    30. Chebi:37510

    31. Nsc-43970

    32. U8cjk0jh5m

    33. Nsc-629313

    34. Chembl46469

    35. Anthralin (usp)

    36. Dithranol (inn)

    37. Nsc629313

    38. Ncgc00091330-01

    39. Dsstox_cid_4538

    40. 1,8-dihydroxy-9(10h)-anthracenone;anthralin

    41. Dsstox_rid_77448

    42. Dsstox_gsid_24538

    43. Dithranolum

    44. Dithranolum [inn-latin]

    45. Zithranol-rr

    46. Ccris 628

    47. Cas-1143-38-0

    48. Sr-05000002011

    49. Einecs 214-538-0

    50. Unii-u8cjk0jh5m

    51. Mfcd00053409

    52. Brn 2054360

    53. Cignoline

    54. Ccris 5592

    55. Prestwick_528

    56. Anthralin, Dithranol

    57. Dithranol ,(s)

    58. Nsc 403736

    59. Brn 1976792

    60. Anthrone,8-dihydroxy-

    61. Spectrum_000056

    62. Anthraderm (tn)

    63. Anthralin [mi]

    64. Dithranol [iarc]

    65. Spectrum2_000111

    66. Spectrum3_000304

    67. Spectrum4_000151

    68. Spectrum5_000820

    69. Anthralin [vandf]

    70. Dithranol [mart.]

    71. Epitope Id:114081

    72. 1,8-dihydroxy-9-anthrane

    73. Anthralin [usp-rs]

    74. Cid_2202

    75. Dithranol [who-dd]

    76. Dithranol [who-ip]

    77. Schembl3197

    78. Bspbio_001868

    79. Kbiogr_000622

    80. Kbioss_000436

    81. 4-06-00-07602 (beilstein Handbook Reference)

    82. Mls001332632

    83. Mls002415712

    84. 1,8,9-trihydroxyanthracene;

    85. Divk1c_000021

    86. Spectrum1500127

    87. Spbio_000122

    88. Zinc1322

    89. Dithranol [ep Impurity]

    90. Dithranol [ep Monograph]

    91. Dithranol, >=90% (hplc)

    92. Dtxsid7024538

    93. Hms500b03

    94. Kbio1_000021

    95. Kbio2_000436

    96. Kbio2_003004

    97. Kbio2_005572

    98. Kbio3_001368

    99. Nuzwlkwwnnjhpt-uhfffaoysa-

    100. Anthralin [usp Monograph]

    101. Ninds_000021

    102. Hms1920e07

    103. Hms2091k07

    104. Hms2271b09

    105. Hms3715h19

    106. Pharmakon1600-01500127

    107. Hy-b0738

    108. Nsc43970

    109. 9(10h)-anthracenone,8-dihydroxy-

    110. Tox21_111115

    111. Tox21_201851

    112. Tox21_300290

    113. Bdbm50041802

    114. Ccg-38920

    115. Nsc755873

    116. S4590

    117. 1,8-dihydroxy-9-(10h)anthracenone

    118. Akos015914122

    119. Tox21_111115_1

    120. Db11157

    121. Ks-5183

    122. Nsc-755873

    123. Idi1_000021

    124. 1,8-dihydroxy-9(10h)-anthracenone #

    125. Ncgc00091330-02

    126. Ncgc00091330-03

    127. Ncgc00091330-04

    128. Ncgc00091330-05

    129. Ncgc00091330-07

    130. Ncgc00253941-01

    131. Ncgc00259400-01

    132. Ac-14842

    133. Nci60_004019

    134. Sbi-0051286.p003

    135. Db-060606

    136. 1,8-dihydroxy-9,10-dihydroanthracen-9-one

    137. Ft-0625372

    138. C06831

    139. D00233

    140. D97650

    141. Ab00051916_07

    142. A803172

    143. Q419397

    144. Sr-05000002011-1

    145. Sr-05000002011-2

    146. W-108602

    147. Dithranol, European Pharmacopoeia (ep) Reference Standard

    148. Anthralin, United States Pharmacopeia (usp) Reference Standard

    149. Anthralin (dithranol), Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 226.23 g/mol
    Molecular Formula C14H10O3
    XLogP33.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass226.062994177 g/mol
    Monoisotopic Mass226.062994177 g/mol
    Topological Polar Surface Area57.5 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity287
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Stable plaque psoriasis of the skin and scalp. It is also used topically in the management of psoriasis, dermatoses, and alopecia areata. Anthralin is also used in biomedical research due to its effect on EGFR autophosphorylation.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Anthralin is a natural anthraquinone derivative, anti-psoriatic and anti-inflammatory agent. It controls skin growth by reducing the synthesis of DNA and the mitotic activity in the hyperplastic epidermis, normalizing the rate of cell proliferation and keratinization.

    5.2 MeSH Pharmacological Classification

    Dermatologic Agents

    Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

    5.3 ATC Code

    D - Dermatologicals

    D05 - Antipsoriatics

    D05A - Antipsoriatics for topical use

    D05AC - Antracen derivatives

    D05AC01 - Dithranol

    5.4 Absorption, Distribution and Excretion

    Absorption

    Anthralin penetrates damaged skin and psoriatic lesions faster and to a greater extent than normal skin, likely due to increased vascularity of psoriatic lesions.

    5.5 Metabolism/Metabolites

    Anthralin is administered topically. Although the extent of systemic absorption after topical application has not been determined, no traces of anthraquinone metabolites were detected in the urine of treated subjects in a limited clinical study of anthralin cream,. Anthralin does not inhibit hepatic microsomal enzyme activity.

    5.6 Mechanism of Action

    Anthralin inhibits the proliferation of keratinocytes (epidermal skin cells), prevents the action of T-cells, and promotes cell differentiation, likely through mitochondrial dysfunction. In addition, the production of free radicals may contribute to its anti-psoriatic effect. In vitro studies demonstrate that anthralin prolongs the prophase component of mitosis for keratinocytes and leukocytes. Prophase is the first step of mitosis, the process separating the duplicated genetic material carried in the nucleus of a parent cell into two identical daughter cells. In vivo studies demonstrate that anthralin blocks DNA synthesis and can increase the release of reactive oxygen species. Anthralin is believed to normalize the rate of epidermal cell proliferation and keratinization by reducing the mitotic activity of the epidermal hyperplasia in psoriasis. Anti-proliferative and anti-inflammatory effects of anthralin have been demonstrated on both psoriatic and healthy skin. The anti-proliferative effects of anthralin are thought to be due to a combination of inhibition of DNA synthesis and its strong reducing properties. The effectiveness of anthralin as an anti-psoriatic agent is partly owed to its ability to promote lipid peroxidation and reduce the concentration of endothelial adhesion molecules, which are found to be elevated in psoriatic patients,. Recent studies suggest that its ability to prevent T-lymphocyte activation and normalize keratinocyte differentiation may occur by a direct effect on mitochondria.

    API Reference Price

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    05-Jan-2021
    25-Oct-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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