idarubicin

{{Short description|Anthracycline antileukemic drug}}

{{Drugbox

| verifiedrevid = 458281600

| IUPAC_name = (1S,3S)-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-L-lyxo-hexopyranoside

| image = Idarubicin.svg

| image2 = Idarubicin ball-and-stick.png

| tradename =

| Drugs.com = {{drugs.com|monograph|idarubicin-hydrochloride}}

| MedlinePlus = a691004

| pregnancy_US = D

| legal_US = Rx-only

| routes_of_administration =

| bioavailability =

| protein_bound = 97%

| metabolism =

| elimination_half-life = 22 hours

| IUPHAR_ligand = 7083

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 58957-92-9

| ATC_prefix = L01

| ATC_suffix = DB06

| ATC_supplemental =

| PubChem = 42890

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01177

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 39117

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ZRP63D75JW

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08062

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 42068

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1117

| C=26 | H=27 | N=1 | O=9

| smiles = O=C2c1c(O)c5c(c(O)c1C(=O)c3ccccc23)C[C@@](O)(C(=O)C)C[C@@H]5O[C@@H]4O[C@H]([C@@H](O)[C@@H](N)C4)C

| 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XDXDZDZNSLXDNA-TZNDIEGXSA-N

| synonyms = 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

}}

Idarubicin {{IPAc-en|ˌ|aɪ|d|ə|ˈ|r|uː|b|ᵻ|s|ɪ|n}} or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts{{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 }} itself into DNA and prevents DNA unwinding by interfering with the enzyme topoisomerase II. It is an analog of daunorubicin, but the absence of a methoxy group increases its fat solubility and cellular uptake.{{cite web | url = http://www.pfizer.com/files/products/uspi_idamycin.pdf | title = Idamycin Package insert | work = Pfizer | date = January 2006 }}

Similar to other anthracyclines, it also induces histone eviction from chromatin.{{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 }}

It belongs to the family of drugs called antitumor antibiotics.

It is currently combined with cytosine arabinoside as a first line treatment of acute myeloid leukemia.{{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 }}

It is used for treatment of acute lymphoblastic leukemia and chronic myelogenous leukemia in blast crisis.{{Cite book|title=Basic & clinical pharmacology| vauthors = Katzung BG |isbn=9781259641152|oclc=1009849139|date = 2017-11-30 | publisher = McGraw-Hill Education }}

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