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Tox21_300290

Tox21_300290

Synopsis, 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

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

Tox21_300290

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 Formula	C₁₄H₁₀O₃
Molecular Weight	226.23 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	226.062994177 g/mol
Monoisotopic Mass	226.062994177 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	287
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.