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Revision as of 11:54, 31 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit Latest revision as of 20:59, 6 January 2024 edit undoCitation bot (talk | contribs)Bots5,457,681 edits Add: doi-access. | Use this bot. Report bugs. | #UCB_CommandLine 
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{{Short description|Anthracycline antileukemic drug}}
{{Drugbox {{Drugbox
| verifiedrevid = 443868004 | verifiedrevid = 458281600
| IUPAC_name = (1''S'',3''S'')-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxo-α-<small>L</small>-''lyxo''-hexopyranoside | IUPAC_name = (1''S'',3''S'')-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxo-α-<small>L</small>-''lyxo''-hexopyranoside
| image = Idarubicin.svg | image = Idarubicin.svg
| image2 = Idarubicin ball-and-stick.png

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| Drugs.com = {{drugs.com|monograph|idarubicin-hydrochloride}} | Drugs.com = {{drugs.com|monograph|idarubicin-hydrochloride}}
| MedlinePlus = a691004 | MedlinePlus = a691004
| pregnancy_category = | pregnancy_US = D
| legal_status = | legal_US = Rx-only
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| metabolism = | metabolism =
| elimination_half-life = 22 hours | elimination_half-life = 22 hours

<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 7083
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 58957-92-9 | CAS_number = 58957-92-9
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1117 | ChEMBL = 1117

<!--Chemical data--> <!--Chemical data-->
| C=26 | H=27 | N=1 | O=9 | C=26 | H=27 | N=1 | O=9
| molecular_weight = 497.494 g/mol
| smiles = O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C(O)(C(=O)C)C5O4O((O)(N)C4)C | smiles = O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C(O)(C(=O)C)C5O4O((O)(N)C4)C
| InChI = 1/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
| InChIKey = XDXDZDZNSLXDNA-TZNDIEGXBV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1 | StdInChI = 1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
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| synonyms = <small>9-acetyl-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione</small> | synonyms = <small>9-acetyl-7-(4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl)oxy-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione</small>
}} }}
'''Idarubicin''' ({{IPAc-en|icon|ˌ|aɪ|d|ə|ˈ|r|uː|b|ɨ|s|ɪ|n}}) or '''4-demethoxydaunorubicin''' is an ] ]. It inserts itself into DNA and prevents DNA from unwinding by interfering with the enzyme ]. It is an analog of ], but the absence of a methoxy group increases its fat solubility and cellular uptake. <ref></ref> '''Idarubicin''' {{IPAc-en|ˌ|aɪ|d|ə|ˈ|r|uː|b|ᵻ|s|ɪ|n}} or '''4-demethoxydaunorubicin''' is an ] ]. It inserts<ref name="Miller">{{cite journal |vauthors=Miller JP, Stoodley RJ |title= Studies directed towards anthracyclinone syntheses: The use of d-glucose as a chiral auxiliary in asymmetric Diels–Alder reactions |journal= J. Saudi Chem. Soc. |volume=17 |pages=29–42 |year=2013 |doi= 10.1016/j.jscs.2011.02.019|doi-access=free }}</ref> itself into DNA and prevents DNA unwinding by interfering with the enzyme ]. It is an analog of ], but the absence of a methoxy group increases its fat solubility and cellular uptake.<ref>{{cite web | url = http://www.pfizer.com/files/products/uspi_idamycin.pdf | title = Idamycin Package insert | work = Pfizer | date = January 2006 }}</ref>
Similar to other anthracyclines, it also induces ] eviction from ].<ref name="Pang">{{cite journal | vauthors = Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, Nieuwland M, Ovaa H, Rottenberg S, van Tellingen O, Janssen J, Huijgens P, Zwart W, Neefjes J | display-authors = 6 | title = Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin | journal = Nature Communications | volume = 4 | pages = 1908 | year = 2013 | pmid = 23715267 | pmc = 3674280 | doi = 10.1038/ncomms2921 | bibcode = 2013NatCo...4.1908P }}</ref>


It belongs to the family of drugs called ]s. It belongs to the family of drugs called ]s.


It is currently combined with ] as a first line treatment of ]. It is currently combined with ] as a first line treatment of ].<ref>{{cite journal | vauthors = Arwanih EY, Louisa M, Rinaldi I, Wanandi SI | title = Resistance Mechanism of Acute Myeloid Leukemia Cells Against Daunorubicin and Cytarabine: A Literature Review | journal = Cureus | volume = 14 | issue = 12 | pages = e33165 | date = December 2022 | pmid = 36726936 | doi = 10.7759/cureus.33165 | doi-access = free | pmc = 9885730 }}</ref>

It is used for treatment of ] and ] in blast crisis.<ref>{{Cite book|title=Basic & clinical pharmacology| vauthors = Katzung BG |isbn=9781259641152|oclc=1009849139|date = 2017-11-30 | publisher = McGraw-Hill Education }}</ref>


It is distributed under the trade names '''Zavedos''' (UK) and '''Idamycin''' (USA). It is distributed under the trade names '''Zavedos''' (UK) and '''Idamycin''' (USA).


==References== == Side effects ==
], ] cramps, ] and ] are common among patients treated with idarubicin.<ref>{{Cite web|url=https://www.drugs.com/sfx/idarubicin-side-effects.html|title=Idarubicin Side Effects: Common, Severe, Long Term|website=Drugs.com|language=en|access-date=2019-06-21}}</ref>

== References ==
{{Reflist}} {{Reflist}}

== External links ==
* in the ]


{{Chemotherapeutic agents}} {{Chemotherapeutic agents}}


] ]
]
] ]



{{antineoplastic-drug-stub}} {{antineoplastic-drug-stub}}

]
]
]
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