SynCED: Idarubicin hydrochloride

Record Information

Version

1.0

Creation Date

2016-05-22 06:20:36 UTC

Update Date

2026-04-05 21:49:24 UTC

Accession Number

CHEM019618

Identification

Common Name

Idarubicin hydrochloride

Class

Small Molecule

Description

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. It is currently combined with cytosine arabinoside as a first line treatment of acute myeloid leukemia. It is used for treatment of acute lymphoblastic leukemia and Chronic myelogenous leukemia in blast crisis.It is distributed under the trade names Zavedos (UK) and Idamycin (USA).

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Idamycin	Kegg
4 Demethoxydaunorubicin	MeSH
IMI 30	MeSH
4-Demethoxydaunorubicin	MeSH
IMI-30	MeSH
Hydrochloride, idarubicin	MeSH
4-Desmethoxydaunorubicin	MeSH
Idarubicin	MeSH
4 Desmethoxydaunorubicin	MeSH
IMI30	MeSH

Chemical Formula

C₂₆H₂₈ClNO₉

Average Molecular Mass

533.955 g/mol

Monoisotopic Mass

533.145 g/mol

CAS Registry Number

57852-57-0

IUPAC Name

(7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione hydrochloride

Traditional Name

idarubicin hydrochloride

SMILES

Cl.[H][C@]1(N)C[C@]([H])(O[C@@]2([H])C[C@@](O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(C)=O)O[C@@]([H])(C)[C@@]1([H])O

InChI Identifier

InChI=1S/C26H27NO9.ClH/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;1H/t10-,15-,16-,17-,21+,26-;/m0./s1

InChI Key

JVHPTYWUBOQMBP-RVFAQHLVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
Amino saccharide
Benzenoid
Oxane
Monosaccharide
Tertiary alcohol
Alpha-hydroxy ketone
Vinylogous acid
1,2-aminoalcohol
Secondary alcohol
Ketone
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Hydrochloride
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Primary amine
Organooxygen compound
Primary aliphatic amine
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.77 g/L	ALOGPS
logP	1.69	ALOGPS
logP	1.9	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	176.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.43 m³·mol⁻¹	ChemAxon
Polarizability	50.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DBSALT000341

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Idarubicin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

636362

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Idarubicin hydrochloride (CHEM019618)

Structure for CHEM019618: Idarubicin hydrochloride