| Revision as of 12:41, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 457167034 of page Mitoxantrone for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 13:28, 29 May 2024 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,491 edits rm "recently" |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 462252883 |
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| Verifiedfields = changed |
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| verifiedrevid = 414758221 |
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| IUPAC_name = 1,4-dihydroxy-5,8-bis-anthracene-9,10-dione |
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| IUPAC_name = 1,4-dihydroxy-5,8-bis-anthracene-9,10-dione |
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| image = Mitoxantrone skeletal.svg |
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| image = Mitoxantrone skeletal.svg |
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| image2 = Mitoxantrone ball-and-stick.png |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = Novantrone |
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| tradename = Novantrone |
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| pregnancy_US = D |
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| pregnancy_US = D |
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| legal_status = Rx-only |
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| legal_status = Rx-only |
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| routes_of_administration = '''Exclusively''' ] |
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| routes_of_administration = Mainly ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = n/a |
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| bioavailability = n/a |
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| elimination_half-life = 75 hours |
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| elimination_half-life = 75 hours |
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| excretion = ] |
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| excretion = ] |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 7242 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 65271-80-9 |
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| CAS_number = 65271-80-9 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D08224 |
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| KEGG = D08224 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 50729 |
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| ChEBI = 50729 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 58 |
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| ChEMBL = 58 |
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| PDB_ligand = MIX |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=22 | H=28 | N=4 | O=6 |
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| C=22 | H=28 | N=4 | O=6 |
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| SMILES = O=C2c1c(c(NCCNCCO)ccc1NCCNCCO)C(=O)c3c2c(O)ccc3O |
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| molecular_weight = 444.481 ]/] |
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| smiles = O=C2c1c(c(NCCNCCO)ccc1NCCNCCO)C(=O)c3c2c(O)ccc3O |
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| InChI = 1/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 |
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| InChIKey = KKZJGLLVHKMTCM-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey = KKZJGLLVHKMTCM-UHFFFAOYSA-N |
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| StdInChIKey = KKZJGLLVHKMTCM-UHFFFAOYSA-N |
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}} |
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}} |
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'''Mitoxantrone''' (INN, BAN, USAN; also known as '''Mitozantrone''' in Australia; trade name '''Novantrone''') is an ] ] agent. |
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==Uses== |
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Mitoxantrone is used to treat certain types of cancer, mostly ]. It improves the survival rate of children suffering from ] relapse.<ref name="Parker">{{cite journal | vauthors = Parker C, Waters R, Leighton C, Hancock J, Sutton R, Moorman AV, Ancliff P, Morgan M, Masurekar A, Goulden N, Green N, Révész T, Darbyshire P, Love S, Saha V | display-authors = 6 | title = Effect of mitoxantrone on outcome of children with first relapse of acute lymphoblastic leukaemia (ALL R3): an open-label randomised trial | journal = Lancet | volume = 376 | issue = 9757 | pages = 2009–2017 | date = December 2010 | pmid = 21131038 | pmc = 3010035 | doi = 10.1016/S0140-6736(10)62002-8 }}</ref> |
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The combination of mitoxantrone and ] is approved as a second-line treatment for metastatic hormone-refractory ]. This combination was once the first line of treatment; however, a combination of ] and prednisone improves survival rates and lengthens the disease-free period.<ref>{{cite book |chapter=Cancer Chemotherapy | vauthors = Katzung BG |title=Basic and clinical pharmacology |publisher=McGraw-Hill Medical Publishing Division |location=New York |year=2006 |isbn=0-07-145153-6 |edition=10th |oclc=157011367}}</ref> |
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Mitoxantrone is also used to treat ] (MS), most notably the ] known as secondary-progressive MS. In the absence of a cure, mitoxantrone is effective in slowing the progression of secondary-progressive MS and extending the time between relapses in both relapsing-remitting MS and progressive-relapsing MS.<ref name="Fox">{{cite journal | vauthors = Fox EJ | title = Management of worsening multiple sclerosis with mitoxantrone: a review | journal = Clinical Therapeutics | volume = 28 | issue = 4 | pages = 461–474 | date = April 2006 | pmid = 16750460 | doi = 10.1016/j.clinthera.2006.04.013 }}</ref> |
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==Side effects== |
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Mitoxantrone, as with other drugs in its class, may cause ] of varying severity, including ], ], ], heart damage and ], possibly with delayed onset. ] is a particularly concerning effect as it is irreversible; thus regular monitoring with ]s or ]s is recommended for patients. |
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Because of the risk of cardiomyopathy, mitoxantrone carries a limit on the cumulative lifetime dose (based on body surface area) in MS patients.<ref name="FDA Postmarket Drug Safety">{{cite web|title=Mitoxantrone Hydrochloride (marketed as Novantrone and generics) – Healthcare Professional Sheet text version|url=https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/ucm126445.htm|publisher=U.S. Food and Drug Administration|access-date=19 September 2014|ref=fdapostmarket}}</ref> |
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==Mechanism of action== |
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Mitoxantrone is a ] ]; it disrupts ] and ] in both healthy cells and cancer cells by ]<ref name="pmid">{{cite journal | vauthors = Mazerski J, Martelli S, Borowski E | title = The geometry of intercalation complex of antitumor mitoxantrone and ametantrone with DNA: molecular dynamics simulations | journal = Acta Biochimica Polonica | volume = 45 | issue = 1 | pages = 1–11 | year = 1998 | pmid = 9701490 | doi = 10.18388/abp.1998_4280 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Kapuscinski J, Darzynkiewicz Z | title = Interactions of antitumor agents Ametantrone and Mitoxantrone (Novatrone) with double-stranded DNA | journal = Biochemical Pharmacology | volume = 34 | issue = 24 | pages = 4203–4213 | date = December 1985 | pmid = 4074383 | doi = 10.1016/0006-2952(85)90275-8 }}</ref> between DNA bases. It is also classified as an antibiotic.<ref>{{Cite web | url=https://livertox.nlm.nih.gov/Mitoxantrone.htm | title=Mitoxantrone}}</ref> |
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== See also == |
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* ], a mitoxantrone ] under development |
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* ] |
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== References == |
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{{Reflist}} |
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== External links == |
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* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/mitoxantrone | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Mitoxantrone }} |
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{{Demyelinating diseases of CNS}} |
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{{Merck Serono|state=autocollapse}} |
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{{Chemotherapeutic agents}} |
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{{Portal bar | Medicine}} |
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