Cas no 58957-92-9 (Idarubicin)

Idarubicin is an anthracycline-class chemotherapeutic agent primarily used in the treatment of acute leukemias, including acute myeloid leukemia (AML) and acute lymphoblastic leukemia (ALL). Its mechanism of action involves intercalation into DNA and inhibition of topoisomerase II, leading to DNA strand breaks and apoptosis in rapidly dividing cells. Compared to other anthracyclines like daunorubicin, idarubicin exhibits superior lipophilicity, enabling enhanced cellular uptake and retention. It also demonstrates a favorable pharmacokinetic profile with active metabolites contributing to prolonged therapeutic effects. The compound is typically administered intravenously and is often incorporated into induction and consolidation therapy regimens due to its efficacy in reducing tumor burden. Careful monitoring of cardiac toxicity is advised due to potential cumulative dose-related effects.
Idarubicin structure
Idarubicin structure
Product Name:Idarubicin
CAS No:58957-92-9
MF:C26H27NO9
MW:497.493888139725
MDL:MFCD00897212
CID:57346
PubChem ID:42890
Update Time:2025-05-20

Idarubicin Chemical and Physical Properties

Names and Identifiers

    • Idarubicin
    • (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
    • 4-demethoxydaunomycin
    • 4-Demethoxydaunorubicin
    • 5,12-naphthacenedione
    • Idamycin
    • Idarubicina
    • Idarubicine
    • Idarubicine [INN-French]
    • Idarubicinum
    • Idarubicinum [INN-Latin]
    • 5,12-Naphthacenedione,9-acetyl-7-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-,(7S-cis)-
    • 1-Demethoxydaunorubicin
    • 4-DMD
    • Demethoxydaunorubicin
    • SR-01000075934
    • IDARUBICIN [WHO-DD]
    • SMR000466355
    • (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
    • (7S,9S)-9-Acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
    • BCP9000773
    • 4-Desmethoxydaunorubicin
    • (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
    • Daunomycin, 4-demethoxy-
    • NCGC00093976-03
    • AB00698511-08
    • SDCCGSBI-0050582.P002
    • HY-17381A
    • SR-01000075934-1
    • 4-DEMETHOXY-DAUNORUBICIN
    • NCGC00093976-02
    • DTXSID7023142
    • Tox21_500600
    • IDARUBICIN [VANDF]
    • AKOS015895563
    • 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)-
    • UNII-ZRP63D75JW
    • MLS001401448
    • Lopac0_000600
    • NSC256439
    • Idarubicinum (INN-Latin)
    • DTXCID503142
    • (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;hydrochloride
    • 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-
    • AB00698511-09
    • NCGC00093976-18
    • A935911
    • (1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSIDE
    • 58957-92-9
    • (1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-hexopyranoside
    • GTPL7083
    • (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione
    • AB00698511_11
    • Idarubicine (INN-French)
    • (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride
    • L01DB06
    • EN300-7479233
    • DB01177
    • CS-0007534
    • (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
    • Idarubicin, United States Pharmacopeia (USP) Reference Standard
    • D08062
    • A832088
    • AB00698511-06
    • Zavedos (TN)
    • XDXDZDZNSLXDNA-TZNDIEGXSA-N
    • EU-0100600
    • HMS2089D05
    • NCGC00261285-01
    • (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
    • IDARUBICIN [MI]
    • BCPP000207
    • NCGC00093976-01
    • NCGC00093976-05
    • BRD-K69650333-001-01-1
    • Idarubicin (INN)
    • CHEMBL1117
    • 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,9S)-
    • AC-9384
    • Idarubicina [INN-Spanish]
    • NSC 256439
    • (1S,3S)-3-ACETYL-1,2,3,4,6,11-HEXAHYDRO-3,5,12-TRIHYDROXY-6,11-DIOXO-1-NAPHTHACENYL 3-AMINO-2,3,6-TRIDEOXY-alpha-L-LYXO-HEXOPYRANOSIDE
    • cid_636362
    • ZRP63D75JW
    • (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
    • (7S,9S)-9-acetyl-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
    • DM5
    • 4 Desmethoxydaunorubicin
    • (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
    • Idarubicin [INN:BAN]
    • Q1063862
    • Idarubicin hydrochloride, solid
    • CCG-204689
    • CCRIS 5083
    • BRD-K69650333-001-02-9
    • CHEBI:42068
    • NCGC00093976-04
    • 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-
    • HMS3261H22
    • 4 Demethoxydaunorubicin
    • Idarubicina (INN-Spanish)
    • 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,9S)-
    • 4-DMDR
    • (7S-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione
    • (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-trideoxy-alpha-L-lyxo-hexopyranoside
    • Idarubicinhydrochloride
    • BDBM58490
    • I 1656
    • LP00600
    • AB00698511-10
    • KBioSS_002388
    • BRD-K69650333-003-14-0
    • SCHEMBL3750
    • IDARUBICIN [INN]
    • NCGC00093976-12
    • 5,12-Naphthacenedione,9-acetyl-7-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S,9S)-
    • BRD-K69650333-003-13-2
    • Idarubicin?
    • MDL： MFCD00897212
    • Inchi： 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
    • InChI Key： XDXDZDZNSLXDNA-TZNDIEGXSA-N
    • SMILES： O([C@H]1C[C@@H]([C@@H]([C@H](C)O1)O)N)[C@@H]1C2C(=C3C(C4C=CC=CC=4C(C3=C(C=2C[C@@](C(C)=O)(C1)O)O)=O)=O)O

Computed Properties

  • Exact Mass: 497.16900
  • Monoisotopic Mass: 497.168581
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 36
  • Rotatable Bond Count: 3
  • Complexity: 912
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 54
  • XLogP3: nothing
  • Topological Polar Surface Area: 177

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.3477 (rough estimate)
  • Melting Point: No data available
  • Boiling Point: 725.435℃ at 760 mmHg
  • Flash Point: 392.5±32.9 °C
  • Refractive Index: 1.6000 (estimate)
  • PSA: 176.61000
  • LogP: 1.72060
  • Vapor Pressure: No data available

Idarubicin Security Information

Idarubicin Pricemore >>

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Idarubicin Related Literature

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Additional information on Idarubicin

Idarubicin: A Comprehensive Overview

Idarubicin, also known by its CAS number 58957-92-9, is a potent anthracycline antibiotic that has garnered significant attention in the field of oncology due to its strong antitumor activity. Derived from the bacterium Streptomyces peucetius, this compound has been extensively studied for its role in chemotherapy, particularly in the treatment of acute leukemias and other malignancies. The development and application of idarubicin represent a milestone in cancer therapy, offering a powerful tool against various forms of cancer.

The chemical structure of idarubicin is characterized by a complex arrangement of rings and functional groups that contribute to its biological activity. This structure allows it to intercalate into DNA, thereby inhibiting topoisomerase II, an enzyme crucial for DNA replication and repair. Recent studies have delved into the molecular mechanisms underlying its efficacy, revealing insights into how it selectively targets cancer cells while minimizing damage to healthy tissues. These findings underscore the importance of understanding the pharmacodynamics of idarubicin to optimize its therapeutic use.

In terms of clinical application, idarubicin has been widely used in combination chemotherapy regimens, particularly in the treatment of acute myeloid leukemia (AML). Its ability to induce remission in AML patients has been well-documented, with studies highlighting its role in improving overall survival rates. Moreover, research into the long-term effects of idarubicin has led to advancements in managing side effects such as cardiotoxicity, a common concern associated with anthracycline use.

The latest research on idarubicin has focused on enhancing its delivery mechanisms to improve efficacy and reduce adverse effects. Nanotechnology-based drug delivery systems, such as liposomal formulations, have shown promise in targeting cancer cells more effectively while sparing normal tissues. These innovations reflect a broader trend toward personalized medicine, where treatments are tailored to individual patient needs based on genetic and molecular profiles.

Additionally, ongoing clinical trials are exploring the potential of combining idarubicin with other anticancer agents to synergize their effects. For instance, studies are investigating the combination of idarubicin with immunotherapy drugs to enhance antitumor immunity. Such approaches aim to leverage the strengths of different therapeutic modalities to achieve better outcomes for patients.

In conclusion, idarubicin, with its CAS number 58957-92-9, remains a cornerstone in cancer chemotherapy due to its potent antitumor properties and versatility in treatment regimens. As research continues to uncover new insights into its mechanisms and applications, the future holds even greater potential for optimizing its use and improving patient care.

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