Basic information
- CAS
58957-92-9- Standard SMILES
CC(=O)[C@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1ccccc1C3=O- InChIKey
XDXDZDZNSLXDNA-TZNDIEGXSA-N- Molecular formula
- C26H27NO9
- Average molar mass
- 497.5 g/mol
- Monoisotopic mass
- 497.16858144
Overview
Idarubicin is a deoxy hexoside, an anthracycline antibiotic and a monosaccharide derivative. It derives from a hydride of a tetracene.
Names & identifiers
- Preferred name
- Idarubicin
- IUPAC
- (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
- English name
- Idarubicin
- Molecular formula
- C26H27NO9
- Molecular weight
- 497.49
Names & synonyms
IDARUBICIN58957-92-94-Demethoxydaunorubicin4-DemethoxydaunomycinIdarubicinaIdarubicineIdarubicinumZavedosZRP63D75JWNSC 256439DTXSID7023142CHEBI:42068
Show more names
DMDR4-DMDCS-704IMI-30IDAMYCINnsc-256439IDARUBICIN HCLIMI-30：NSC-256439Idarubicin USP/EP/BP
(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-dione5,12-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)-(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-hexopyranoside4-Desmethoxydaunorubicin4 Demethoxydaunorubicin(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-dione4 DesmethoxydaunorubicinRefChem:56926
Database identifiers
- CAS
58957-92-9- PubChem CID
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 3
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 912
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP0.2
Solubility7.72e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Anthracyclines; Antibiotics, Antineoplastic; Topoisomerase II Inhibitors
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 589.46 °C · 589.46°C (rough estimate)
- Density
- 1.3477 · 1.3477 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- form
- solid
- pka
- 4.73 · pKa 4.73± 0.21 (Uncertain)
- NCI Dictionary of Cancer Terms
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
idarubicin
DILI Negative
Intravenous
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- HB7877000
- ridadr
- UN 2811 6.1/PG 2
- risk_code
- 60-61-28-40
- hazard_code
- T+
- safety_code
- 53-45
Chemistry & industry
Pharmacology
ATC Code
L01DB06
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Protein Binding97%
Pharmacodynamics
Idarubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Idarubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Idarubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Mechanism of Action
Idarubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Idarubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.
Biological Half-Life22 hours
FDA Pharmacological Classification
ZRP63D75JW
IDARUBICIN
Established Pharmacologic Class [EPC] - Anthracycline Topoisomerase Inhibitor
Chemical Structure [CS] - Anthracyclines
Mechanisms of Action [MoA] - Topoisomerase Inhibitors
Idarubicin is an Anthracycline Topoisomerase Inhibitor. The mechanism of action of idarubicin is as a Topoisomerase Inhibitor.
Related reactions
0 records
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Compound notes
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