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Chemistry

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Also known as: 3902-71-4, Trioxysalen, Trisoralen, Trimethylpsoralen, 4,5',8-trimethylpsoralen, 2',4,8-trimethylpsoralen

Molecular Formula

C₁₄H₁₂O₃

Molecular Weight

228.24 g/mol

InChI Key

FMHHVULEAZTJMA-UHFFFAOYSA-N

FDA UNII

Y6UY8OV51T

Pigmenting photosensitizing agent obtained from several plants, mainly Psoralea corylifolia. It is administered either topically or orally in conjunction with ultraviolet light in the treatment of vitiligo.

Trioxsalen is a Psoralen.

1 2D Structure

Trioxsalen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,5,9-trimethylfuro[3,2-g]chromen-7-one

2.1.2 InChI

InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3

2.1.3 InChI Key

FMHHVULEAZTJMA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C

2.2 Other Identifiers

2.2.1 UNII

Y6UY8OV51T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,5,9-trimethyl-7h-furo(3,2-g)benzopyran-7-one

2. 4,5',8-trimethylpsoralen

3. Nsc 71047

4. Nsc-71047

5. Nsc71047

6. Trimethylpsoralen

7. Trioxisalenum

8. Trioxysalen

9. Trisoralen

2.3.2 Depositor-Supplied Synonyms

1. 3902-71-4

2. Trioxysalen

3. Trisoralen

4. Trimethylpsoralen

5. 4,5',8-trimethylpsoralen

6. 2',4,8-trimethylpsoralen

7. Nsc-71047

8. 2,5,9-trimethyl-7h-furo[3,2-g]chromen-7-one

9. Elder 8011

10. Trioxisaleno

11. Trioxysalene

12. Trioxysalenum

13. 4,5',8-trimethylpsoralene

14. Nsc71047

15. 2,5,9-trimethylfuro[3,2-g]chromen-7-one

16. 7h-furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-

17. Tmp (psoralen)

18. 4,8,5'-trimethylpsoralen

19. 2,5,9-trimethylfuro[3,2-g]benzopyran-7-one

20. Trioxysalen [inn]

21. Trioxsalin

22. 2,5,9-trimethyl-7h-furo(3,2-g)(1)benzopyran-7-one

23. Mfcd00005010

24. Trisoralen;trioxysalen;tmp

25. Y6uy8ov51t

26. 7h-furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl-

27. Chebi:28329

28. Ncgc00016643-01

29. Cas-3902-71-4

30. Dsstox_cid_3716

31. Dsstox_rid_77160

32. Dsstox_gsid_23716

33. Trioxsalen [usan]

34. 6-hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic Acid, Delta-lactone

35. Trioxysalene [inn-french]

36. Trioxysalenum [inn-latin]

37. Trioxisaleno [inn-spanish]

38. Nsc 71047

39. Lactone

40. Sr-01000812969

41. Trioxsalen [usan:usp]

42. Einecs 223-459-0

43. 2,5,9-trimethylpsoralen

44. 4,5,8-trimethylpsoralen

45. Unii-y6uy8ov51t

46. Antipsoriatic

47. Brn 0221723

48. Trioxalen

49. Trixsalen

50. Trisoralen (tn)

51. Trioxsalen (usp)

52. Prestwick_148

53. 7-oxo-2,5,9-trimethyl-7h-furo(3,2-g)(1)benzopyron

54. 4,8-trimethylpsoralen

55. Spectrum_000169

56. 4,8-trimethylpsoralene

57. Trioxsalen [mi]

58. 2',8-trimethylpsoralen

59. Trioxysalen (jan/inn)

60. 6-hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic Acid Gamma-lactone

61. Prestwick0_000709

62. Prestwick1_000709

63. Prestwick2_000709

64. Prestwick3_000709

65. Spectrum2_001083

66. Spectrum3_001378

67. Spectrum4_000883

68. Spectrum5_001557

69. Trioxysalen [jan]

70. Trioxsalen [vandf]

71. Schembl1252

72. Chembl1475

73. Trioxsalen [usp-rs]

74. Trioxysalen [mart.]

75. Oprea1_203343

76. Bspbio_000897

77. Bspbio_002936

78. Kbiogr_001286

79. Kbioss_000649

80. Trioxysalen [who-dd]

81. 5-19-04-00472 (beilstein Handbook Reference)

82. Mls001173417

83. Divk1c_000380

84. Spectrum1500596

85. Spbio_001126

86. Spbio_002818

87. Bpbio1_000987

88. Megxm0_000462

89. Zinc2226

90. Dtxsid3023716

91. Trioxsalen [orange Book]

92. Acon0_000603

93. Acon1_000251

94. Hms501c22

95. Kbio1_000380

96. Kbio2_000649

97. Kbio2_003217

98. Kbio2_005785

99. Kbio3_002156

100. Trioxsalen [usp Impurity]

101. Ninds_000380

102. Hms1570m19

103. Hms1921i05

104. Hms2092a12

105. Hms2097m19

106. Hms2879m06

107. Hms3714m19

108. Pharmakon1600-01500596

109. 7h-furo[3, 2,5,9-trimethyl-

110. Hy-b1157

111. Tox21_110541

112. Ccg-39937

113. Nsc757371

114. Stl564342

115. Akos015912601

116. Tox21_110541_1

117. Trioxsalen, >=98% (hplc), Powder

118. Cs-4760

119. Db04571

120. Ks-5184

121. Nsc-757371

122. Sdccgmls-0066609.p001

123. Trioxysalen 100 Microg/ml In Methanol

124. Idi1_000380

125. Ncgc00016643-02

126. Ncgc00016643-03

127. Ncgc00016643-04

128. Ncgc00016643-05

129. Ncgc00016643-06

130. Ncgc00016643-09

131. Ncgc00016643-10

132. Ncgc00094804-01

133. Ncgc00094804-02

134. Ncgc00178384-01

135. Ncgc00178384-02

136. Ncgc00178384-03

137. Nci60_038883

138. Smr000538905

139. 4,5',8-trimethylpsoralen [iarc]

140. Sbi-0051547.p002

141. Db-049366

142. Ft-0603651

143. T2267

144. Benzofuranacrylic Acid,2,7-trimethyl-,

145. C09314

146. D01034

147. T72416

148. 4,7,9-trimethyl-2h-furo[3,2-g]chromen-2-one

149. Ab00052119_09

150. 2,5,9-trimethyl-7-furo[3,2-g][1]benzopyranone

151. 902t714

152. A824380

153. Q854263

154. 2,5,9-trimethyl-7h-furo[3,2-g]chromen-7-one #

155. Sr-01000812969-2

156. Sr-01000812969-5

157. Sr-01000812969-6

158. Sr-01000812969-7

159. 2,9-trimethyl-7h-furo[3,2-g][1]benzopyran-7-one

160. Brd-k54790157-001-06-4

161. Brd-k54790157-001-10-6

162. Z1551429738

163. 5-benzofuranacrylic Acid,2,7-trimethyl-, .delta.-lactone

164. Trioxsalen, United States Pharmacopeia (usp) Reference Standard

165. 5-benzofuranacrylic Acid, 6-hydroxy-.beta.,2,7-trimethyl-, .delta.-lactone

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₂O₃
Molecular Weight	228.24 g/mol
XLogP3	3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	228.078644241 g/mol
Monoisotopic Mass	228.078644241 g/mol
Topological Polar Surface Area	39.4 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	374
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

Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.

5.2 MeSH Pharmacological Classification

Photosensitizing Agents

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

TRIOXSALEN

5.3.2 FDA UNII

Y6UY8OV51T

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Psoralens

5.4 ATC Code

D - Dermatologicals

D05 - Antipsoriatics

D05A - Antipsoriatics for topical use

D05AD - Psoralens for topical use

D05AD01 - Trioxysalen

D - Dermatologicals

D05 - Antipsoriatics

D05B - Antipsoriatics for systemic use

D05BA - Psoralens for systemic use

D05BA01 - Trioxysalen

5.5 Mechanism of Action

After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.

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API Reference Price

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