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Mitoxantrone

Mitoxantrone

Synopsis, Chemistry

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Also known as: 65271-80-9, Mitoxanthrone, Mitozantrone, Dhaq, Mitoxantron, Novantrone

Molecular Formula

C₂₂H₂₈N₄O₆

Molecular Weight

444.5 g/mol

InChI Key

KKZJGLLVHKMTCM-UHFFFAOYSA-N

FDA UNII

BZ114NVM5P

An anthracenedione-derived antineoplastic agent.

Mitoxantrone is a Topoisomerase Inhibitor. The mechanism of action of mitoxantrone is as a Topoisomerase Inhibitor.

1 2D Structure

Mitoxantrone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione

2.1.2 InChI

InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2

2.1.3 InChI Key

KKZJGLLVHKMTCM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO

2.2 Other Identifiers

2.2.1 UNII

BZ114NVM5P

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acetate, Mitoxantrone

2. Cl 232325

3. Cl-232325

4. Cl232325

5. Dhaq

6. Hydrochloride, Mitoxantrone

7. Mitoxantrone Acetate

8. Mitoxantrone Hydrochloride

9. Mitozantrone

10. Mitroxone

11. Novantron

12. Novantrone

13. Nsc 279836

14. Nsc 287836

15. Nsc 299195

16. Nsc 301739

17. Nsc 301739d

18. Nsc-279836

19. Nsc-287836

20. Nsc-299195

21. Nsc-301739

22. Nsc-301739d

23. Nsc279836

24. Nsc287836

25. Nsc299195

26. Nsc301739

27. Nsc301739d

28. Onkotrone

29. Pralifan

30. Ralenova

2.3.2 Depositor-Supplied Synonyms

1. 65271-80-9

2. Mitoxanthrone

3. Mitozantrone

4. Dhaq

5. Mitoxantron

6. Novantrone

7. Mitoxantrona

8. Mitoxantronum

9. Mitoxantrone [inn]

10. Misostol

11. Nsc 279836

12. Nsc-279836

13. Dhad

14. Nsc279836

15. 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione

16. Mitoxantrone (inn)

17. Mitoxantrone Free Base

18. 1,4-bis(2-(2-hydroxyethylamino)ethyl)amino)-5,8-dihydroxyanthraquinone

19. Bz114nvm5p

20. 5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxyanthraquinone

21. 1,4-dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthracenedione

22. 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-anthracenedione

23. 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione

24. Mls002703044

25. Chebi:50729

26. 65271-80-9 (free Base)

27. Mfcd00242942

28. 9,10-anthracenedione, 1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-

29. Mitoxantronum [inn-latin]

30. Mitoxantrona [inn-spanish]

31. Nsc299195

32. Nsc301739

33. 1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione

34. 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione

35. Anthraquinone, 5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxy-

36. Mix

37. 1,4-dihydroxy-5,8-bis[2-[(1,1,2,2-tetradeuterio-2-hydroxyethyl)amino]ethylamino]anthracene-9,10-dione

38. Mls001333711

39. 9,10-anthracenedione, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-

40. Misostol (tn)

41. 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-dihydroanthracene-9,10-dione

42. Ccris 7604

43. Ncgc00015693-02

44. Mitoxantrone (free Base)

45. Smr000058480

46. Mitoxantrone [inn:ban]

47. Cas-70476-82-3

48. Unii-bz114nvm5p

49. Dhaq (*diacetate Salt*)

50. Brn 2795126

51. Sr-01000076001

52. Mitoxantrone Base

53. 1,4-dihydroxy-5,8-bis(5-hydroxy-3-azapentylamino)anthrachinon

54. 2fum

55. 1,4-dihydroxy-5,8-bis(2-(2-hydroxyethylamino)ethylamino)anthracene-9,10-dione

56. 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthracene-9,10-dione

57. Immunex (salt/mix)

58. Spectrum_001655

59. Chembl58

60. Prestwick0_000385

61. Prestwick1_000385

62. Prestwick2_000385

63. Prestwick3_000385

64. Spectrum2_000908

65. Spectrum3_001590

66. Spectrum4_000866

67. Spectrum5_001205

68. Lopac-m-6545

69. Mitoxantrone [mi]

70. Mitoxantrone [iarc]

71. Cid_4212

72. Neuro_000153

73. Schembl3000

74. 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthra-9,10-quinone

75. Mitoxantrone [vandf]

76. Bidd:pxr0181

77. Lopac0_000779

78. Bspbio_000569

79. Bspbio_003160

80. Kbiogr_001531

81. Kbioss_002135

82. Divk1c_000516

83. Mitoxantrone [who-dd]

84. Spbio_000756

85. Spbio_002490

86. Bpbio1_000627

87. Gtpl7242

88. Dtxsid4046947

89. Bdbm67690

90. Cid_5458171

91. Kbio1_000516

92. Kbio2_002135

93. Kbio2_004703

94. Kbio2_007271

95. Kbio3_002660

96. Ninds_000516

97. Hms2090d05

98. Hms3655e20

99. Kuc108634n

100. Bcp02861

101. Zinc3794794

102. Ccg-36371

103. S1889

104. Stk631833

105. Mitoxantrone Hydrochloride (salt/mix)

106. Akos005564036

107. Bcp9000931

108. Db01204

109. Ksc-19-204

110. Sdccgsbi-0050757.p004

111. Idi1_000516

112. Smp2_000179

113. Ncgc00015693-01

114. Ncgc00015693-03

115. Ncgc00015693-04

116. Ncgc00015693-05

117. Ncgc00015693-06

118. Ncgc00015693-08

119. Ncgc00015693-13

120. Ncgc00015693-23

121. Ncgc00162251-01

122. As-35321

123. Hy-13502

124. Mitoxantrone, Mitoxantrone Hydrochloride, Mitoxantrone Dihydrochloride, Mitoxanthrone Hydrochloride

125. Nci60_002276

126. Nci60_002535

127. Smr001549953

128. Sy226320

129. Sbi-0050757.p003

130. Ab00053716

131. Ft-0630752

132. Ft-0672423

133. M3133

134. Sw196745-6

135. Vu0244399-2

136. 71m809

137. D08224

138. Ab00053716-18

139. Ab00053716-19

140. Ab00053716-22

141. Ab00053716_23

142. Ab00053716_24

143. Q239426

144. Sr-01000076001-7

145. Brd-k21680192-001-01-5

146. Brd-k21680192-001-11-4

147. Brd-k21680192-300-05-2

148. Brd-k21680192-300-07-8

149. Brd-k21680192-300-09-4

150. Brd-k21680192-300-10-2

151. Brd-k21680192-300-12-8

152. 1,4-bis[2-(2-hydroxyethylamino)-ethylamino]-5,8-dihydroxyanthraquinone

153. 1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone

154. 1,4-dihydroxy-5,8-bis[[2-(2-hydroxyethylamino)ethyl]amino]anthraquinone

155. 9, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl] Amino]-

156. 1,4-bis[[2-[(2-hydroxyethyl)amino]ethyl]imino]-1,4-dihydroanthracene-5,8,9,10-tetrol

157. 1,4-dihydroxy-5,8-bis-[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthraquinone

158. 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]-9,10-anthraquinone;hydrochloride

159. 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione;hydrochloride

160. 1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8-bis(oxidanyl)anthracene-9,10-dione;hydrochloride

161. Mitoxantrone; 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthra-9,10-quinone

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₈N₄O₆
Molecular Weight	444.5 g/mol
XLogP3	1
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	444.20088463 g/mol
Monoisotopic Mass	444.20088463 g/mol
Topological Polar Surface Area	163 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	571
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

For the treatment of secondary (chronic) progressive, progressive relapsing, or worsening relapsing-remitting multiple sclerosis

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Mitoxantrone has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

MITOXANTRONE

5.3.2 FDA UNII

BZ114NVM5P

5.3.3 Pharmacological Classes

Topoisomerase Inhibitors [MoA]; Topoisomerase Inhibitor [EPC]

5.4 ATC Code

L01DB07

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01D - Cytotoxic antibiotics and related substances

L01DB - Anthracyclines and related substances

L01DB07 - Mitoxantrone

5.5 Absorption, Distribution and Excretion

Absorption

Poorly absorbed following oral administration

Volume of Distribution

1000 L/m2

Clearance

21.3 L/hr/m2 [Elderly patients with breast cancer receiving IV administration of 15-90 mg/m2]

28.3 L/hr/m2 [Non-elderly patients with nasopharyngeal carcinoma receiving IV administration of 15-90 mg/m2]

16.2 L/hr/m2 [Non-elderly patients with malignant lymphoma receiving IV administration of 15-90 mg/m2]

5.6 Metabolism/Metabolites

Hepatic

5.7 Biological Half-Life

75 hours

5.8 Mechanism of Action

Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity.