Cas no 54193-28-1 (Doxorubicinol (>90%))

Doxorubicinol (>90%) is a primary metabolite of doxorubicin, a widely used anthracycline chemotherapeutic agent. This compound is of significant interest in pharmacological and toxicological research due to its role in mediating both the therapeutic effects and cardiotoxicity associated with doxorubicin therapy. With a purity exceeding 90%, this high-quality standard ensures reliability for analytical and investigative applications, including metabolite profiling, pharmacokinetic studies, and mechanistic research. Its well-characterized structure and stability make it suitable for use as a reference standard in HPLC, LC-MS, and other chromatographic or spectroscopic techniques. Researchers value its consistency for elucidating metabolic pathways and evaluating drug interactions.
Doxorubicinol (>90%) structure
Doxorubicinol (>90%) structure
Product Name:Doxorubicinol (>90%)
CAS No:54193-28-1
MF:C27H31NO11
MW:545.535148859024
CID:369178
PubChem ID:83970
Update Time:2025-06-10

Doxorubicinol (>90%) Chemical and Physical Properties

Names and Identifiers

    • 5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-,(8S,10S)-
    • 5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihy...
    • 5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-8-[(1S)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro
    • ADRIAMYCINOL
    • DOXORUBICINOL-D3
    • 14-hydroxydaunomycinone
    • 7,8,9,10-Tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxy acetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione
    • 8-glycoloyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-Naphthacenedione
    • Adriamycin-aglycon
    • adriamycinaglycone
    • Ccris 7633
    • doxorubicin aglycone
    • doxorubicin hydroxyaglycone
    • Doxorubicinol
    • Doxorubicinone
    • epiru
    • Epirubicin aglycon
    • Epirubicin aglycone
    • RP-27706
    • 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-((1S)-1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8S,10S)-
    • (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-[(1S)-1,2-dihydroxyethyl]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
    • (1S,3S)-3-[(1S)-1,2-dihydroxyethyl]-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
    • NKZRZOVSJNSBFR-FEMMEMONSA-N
    • UNII-HUH05KI4CF
    • adriamycinol hydrochloride
    • (8S)-10-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-8-((S)-1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
    • Q27280114
    • 13-Dihydroadriamycin hydrochloride
    • 13-Dihydrodoxorubicin
    • CS-0081325
    • 63950-05-0
    • (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
    • (7S,9S)-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-9-((1S)-1,2-dihydroxyethyl)-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
    • RP 27706
    • (1S,3S)-3-((1S)-1,2-dihydroxyethyl)-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
    • 13-Dihydrodoxorubicin hydrochloride
    • HY-121259
    • 54193-28-1
    • (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy)-8-((1S)-1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
    • Antibiotic 27706RP
    • Doxorubicinol (hydrochloride)
    • Doxorubicinol (>90%)(Mixture of Diastereomers)
    • (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-8-[1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione hydrochloride
    • DTXSID70920620
    • CHEBI:133817
    • CHEMBL3277946
    • (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-8-((S)-1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
    • AKOS040746779
    • HUH05KI4CF
    • Doxorubicinol (>90%)
    • 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-(1,2-dihydroxyethyl)-1-methoxy-6,8,11-trihydroxy-, (8S-(8-alpha,8(R*),10-alpha))-
    • Inchi: InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3
    • InChI Key: NKZRZOVSJNSBFR-UHFFFAOYSA-N
    • SMILES: COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(O)C(C)O5)c4c(O)c3C(=O)c12)C(O)CO

Computed Properties

  • Exact Mass: 545.18971080g/mol
  • Monoisotopic Mass: 545.18971080g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 39
  • Rotatable Bond Count: 5
  • Complexity: 935
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 7
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.3
  • Topological Polar Surface Area: 209?2

Doxorubicinol (>90%) Pricemore >>

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Additional information on Doxorubicinol (>90%)

Introduction to Doxorubicinol (>90%) and Its Significance in Modern Medicinal Chemistry

The compound with the CAS number 54193-28-1, identified as Doxorubicinol (>90%), represents a critical derivative in the realm of oncology and medicinal chemistry. This high-purity enol form of doxorubicin, a well-known anthracycline antibiotic, has garnered significant attention due to its distinct pharmacological properties and potential therapeutic applications. Doxorubicinol, characterized by its chemical structure and stability, plays a pivotal role in the development of novel chemotherapeutic agents and research methodologies.

In recent years, advancements in synthetic methodologies have enabled the production of Doxorubicinol (>90%) with unprecedented purity, which is essential for rigorous scientific investigation. The compound's enolic form is particularly noteworthy for its enhanced solubility and bioavailability compared to its parent molecule, doxorubicin. This improvement in physicochemical properties has opened new avenues for drug formulation and delivery systems, particularly in targeted therapies.

The pharmacological profile of Doxorubicinol (>90%) has been extensively studied, revealing its potent cytotoxic effects against a broad spectrum of cancer cell lines. Research indicates that doxorubicinol exhibits mechanisms of action similar to those of doxorubicin, including interference with DNA replication and transcription by intercalating into nucleic acids. However, the enolic derivative demonstrates unique interactions with biological targets, which may contribute to reduced toxicity in certain clinical settings.

One of the most compelling aspects of Doxorubicinol (>90%) is its potential in overcoming multidrug resistance (MDR), a significant challenge in cancer treatment. Studies have shown that doxorubicinol can effectively bypass P-glycoprotein-mediated efflux mechanisms, thereby enhancing the efficacy of chemotherapy regimens. This property is particularly relevant in the context of refractory cancers where traditional anthracyclines have limited effectiveness.

Recent clinical trials have explored the use of Doxorubicinol (>90%) as a monotherapy and in combination with other chemotherapeutic agents. The results suggest that it may offer improved outcomes in patients with advanced-stage malignancies, particularly when used alongside novel targeted therapies or immunotherapies. The compound's ability to modulate tumor microenvironment dynamics has also been a focus of investigation, with preliminary data indicating its potential to enhance anti-tumor immune responses.

The synthesis and characterization of Doxorubicinol (>90%) have been refined through cutting-edge techniques such as high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. These methods ensure that the compound meets stringent quality standards required for preclinical and clinical studies. The availability of high-purity doxorubicinol has facilitated innovative research approaches, including structure-activity relationship (SAR) studies and computational modeling.

In the context of drug development, Doxorubicinol (>90%) serves as a valuable intermediate for designing next-generation anthracyclines with improved pharmacokinetic profiles. Its enolic form allows for modifications at various positions on the anthracycline scaffold, enabling researchers to fine-tune properties such as potency, selectivity, and metabolic stability. Such modifications are crucial for developing drugs that can be administered more frequently or with lower systemic toxicity.

The role of Doxorubicinol (>90%) in personalized medicine cannot be overstated. By leveraging genetic and molecular profiling, clinicians can identify patients who are likely to benefit most from doxorubicinol-based therapies. This approach aligns with the broader trend toward precision oncology, where treatments are tailored to individual patient characteristics rather than generalized protocols.

Future research directions for Doxorubicinol (>90%) include exploring its potential in treating non-malignant conditions such as autoimmune diseases and inflammatory disorders. Preliminary evidence suggests that its ability to modulate immune cell function may translate into therapeutic benefits beyond oncology. Additionally, investigating its role in combination regimens with radiation therapy or photodynamic therapy could uncover synergistic effects that enhance treatment outcomes.

The industrial production of Doxorubicinol (>90%) has been optimized to meet global demand while adhering to sustainable practices. Manufacturers are increasingly adopting green chemistry principles to minimize waste and energy consumption during synthesis. These efforts not only reduce environmental impact but also ensure cost-effective production processes that make advanced therapies more accessible to patients worldwide.

In conclusion,Doxorubicinol (>90%), identified by CAS number 54193-28-1, represents a cornerstone compound in modern medicinal chemistry. Its unique pharmacological properties, combined with advancements in synthetic methodologies and clinical research, position it as a promising candidate for next-generation therapeutics. As our understanding of cancer biology evolves,Doxorubicinol (>90%) will continue to play a pivotal role in shaping the future of oncology treatment.

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