Idarubicin hydrochloride (CHEM019618)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:20:36 UTC
Update Date2016-11-09 01:16:02 UTC
Accession NumberCHEM019618
Identification
Common NameIdarubicin hydrochloride
ClassSmall Molecule
DescriptionIdarubicin 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 TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
IdamycinKegg
4 DemethoxydaunorubicinMeSH
IMI 30MeSH
4-DemethoxydaunorubicinMeSH
IMI-30MeSH
Hydrochloride, idarubicinMeSH
4-DesmethoxydaunorubicinMeSH
IdarubicinMeSH
4 DesmethoxydaunorubicinMeSH
IMI30MeSH
Chemical FormulaC26H28ClNO9
Average Molecular Mass533.955 g/mol
Monoisotopic Mass533.145 g/mol
CAS Registry Number57852-57-0
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 Nameidarubicin hydrochloride
SMILESCl.[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 IdentifierInChI=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 KeyJVHPTYWUBOQMBP-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAnthracyclines
Sub ClassNot Available
Direct ParentAnthracyclines
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP1.69ALOGPS
logP1.9ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)8.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area176.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity126.43 m³·mol⁻¹ChemAxon
Polarizability50.83 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-f09d02b4192d4816aec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000090000-f09d02b4192d4816aec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0000090000-f09d02b4192d4816aec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-26c85f2de6373f9edb15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0000090000-26c85f2de6373f9edb15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0000090000-26c85f2de6373f9edb15Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000341
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIdarubicin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID636362
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available