Structure via PubChem · Public domain (PubChem)
idarubicin
Sign in to saveAlso known as Idamycin®, IMI-30, Zavedos®, Idarubicine, (1S,3S)-3-Acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, 4-Demethoxydaunomycin, 5,12-Naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-, Idarubicina
Idarubicin or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts 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. Similar to other anthracyclines, it also induces histone eviction from chromatin.
Chemical data
- Formula
- C26H27NO9
- Molecular weight
- 497.5 g/mol
- IUPAC name
- (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
- SMILES
- C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)C)O)N)O
- InChIKey
- XDXDZDZNSLXDNA-TZNDIEGXSA-N
- XLogP
- 1.9
- Polar surface area
- 177 Ų
- H-bond donors
- 5
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1990
- Admin. routes
- parenteral
- Indications
- hepatocellular carcinoma, myelodysplastic syndrome, acute lymphoblastic leukemia, acute monocytic leukemia
via ChEMBL · EBI
Research
2,734 papers- Idarubicin.Tumori · 2002
- Randomized study of induction therapy comparing standard-dose idarubicin with high-dose daunorubicin in adult patients with previously untreated acute myeloid leukemia: the JALSG AML201 Study.Blood · 2011
- Idarubicin versus Epirubicin in Transarterial Chemoembolization for Barcelona Clinic Liver Cancer Stage B Hepatocellular Carcinoma: An Open-label, Randomized, Phase IV Trial.Radiology · 2025
- Idarubicin: a second-generation anthracycline.DICP : the annals of pharmacotherapy · 1991
- Idarubicin.Journal of pediatric oncology nursing : official journal of the Association of Pediatric Oncology Nurses · 1990
via PubMed
Wikidata facts
- Subclass of
- anthracycline antibiotic
- Mass
- 497.169
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₆H₂₇NO₉
- World Health Organisation international non-proprietary name
- idarubicin
- medical condition treated
- acute promyelocytic leukemia
- isomeric SMILES
- C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)C)O)N)O
- canonical SMILES
- CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=CC=CC=C5C4=O)O)(C(=O)C)O)N)O
- Commons category
- Idarubicin
- stylized name
- IDArubicin
Sources (6)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Side effects
- References
- External links
Idarubicin or 4-demethoxydaunorubicin is an anthracycline antileukemic drug. It inserts 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. Similar to other anthracyclines, it also induces histone eviction from chromatin.
It belongs to the family of drugs called antitumor antibiotics.
Excerpted from Wikipedia’s “idarubicin” article, available under the CC BY-SA 4.0 licence.