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    DHAQ (*Diacetate salt*)

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    2D Structure
    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

    2D Structure

    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 Weight 444.5 g/mol
    Molecular Formula C22H28N4O6
    XLogP31
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count12
    Exact Mass444.20088463 g/mol
    Monoisotopic Mass444.20088463 g/mol
    Topological Polar Surface Area163 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity571
    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

    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.