Doxorubicin EP Impurity A (Daunorubicin) - CAS 20830-81-3

Doxorubicin EP Impurity A (Daunorubicin) - CAS 20830-81-3 Catalog number: BADC-00042

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Daunomycin is an anthracycline antibiotic produced by Streptomyces peucetius. The mechanism of action is the same as that of doxorubicin, which is inserted into DNA and inhibits RNA and DNA synthesis. It is mainly used for the treatment of acute myeloid and lymphocytic leukemia, with adverse reactions such as cardiotoxicity and bone marrow suppression. It has anti-gram-positive bacteria, negative bacteria and tumor activity.

ADCs Cytotoxin
Product Name
Doxorubicin EP Impurity A (Daunorubicin)
Catalog Number
Molecular Formula
Molecular Weight
Doxorubicin EP Impurity A (Daunorubicin)

Ordering Information

Catalog Number Size Price Quantity
BADC-00042 -- $--
Daunomycin is an anthracycline antibiotic produced by Streptomyces peucetius. The mechanism of action is the same as that of doxorubicin, which is inserted into DNA and inhibits RNA and DNA synthesis. It is mainly used for the treatment of acute myeloid and lymphocytic leukemia, with adverse reactions such as cardiotoxicity and bone marrow suppression. It has anti-gram-positive bacteria, negative bacteria and tumor activity.
(8S,10S)-8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione; Daunomycin; Acetyladriamycin; Leukaemomycin C; Cerubidine; Rubidomycin; (1S,3S)-3-Acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside; RP-13057; NSC 82151; (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione; Epirubicin EP Impurity D
Canonical SMILES
1.554 g/cm3
Soluble in Methanol, Water
Melting Point
Flash Point
419.5±32.9 °C
Index Of Refraction
Optical Rotation
Thin red needles; decomposes 188-190 °C. Specific optical rotation: +248 deg (c = 0.05-1.0 in methanol); soluble in water, methanol, aqueous alcohols; practically insoluble in chloroform, ether, benzene. Color of aqueous solution changes from pink at acid pH to blue at alkaline pH. Adsorption max (methanol): 234, 252, 290, 480, 495, and 532 nm (epsilon 1%, 1cm: 665, 462, 153, 214, 218 and 112) /Daunorubicin hydrochloride/
Vapor Pressure
0.0±2.8 mmHg at 25°C
UV Spectra
Max adsorbance = 234 nm (epsilon = 711 for 1% solution, 1 cm path); 252 nm (epsilon = 494); 290 nm (epsilon = 163); 480 nm (epsilon = 227); 495 nm (epsilon = 214); 532 nm (epsilon = 214)
Mechanism Of Action
Daunorubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Daunorubicin 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.
Daunorubicin 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. Daunorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Daunorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
Toxicity (LD50)
LD50=20 mg/kg (mice, IV); LD50=13 mg/kg (rat, IV).
In Vitro
Normal citrated platelet-rich plasma was reacted in vitro with daunomycin and/or collagen with structural assessment by phase and electron microscopy and functional studies by platelet aggregation, [2-14C]5-hydroxytryptamine release studies and assays for released cytoplasmic marker enzyme, lactic dehydrogenase, in the supernatant fluid. High [greater than 0.04 mg/ml (greater than 0.07 mM)] concentrations of daunomycin were associated with structural changes, specifically by platelet swelling, vacuole formation and mitochondrial swelling with interruption of the trilaminar membrane. Platelets, exposed to low doses of daunomycin, 0.001 to 0.01 mg/ml (0.00177-0.0177 mM) of platelet-rich plasma, were dysfunctional with decreased aggregation with collagen and decreased [2-14C]5-hydroxytryptamine release.
In Vivo
In vivo imaging of the fluorescence signal generated by daunomycin indicated uptake of both conjugate and daunomycin by the tumour. Tumour fluorescence was, however, higher in the conjugate treated mice than in the daunomycin treated mice, thus suggesting specific delivery of the drug to the tumour. Histological examination of myocardial tissue indicated that only the daunomycin, but not conjugate treated mice showed cardiac damage.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT02914977Acute Lymphocytic LeukemiaPhase 12021-04-29Tara LinActive, not recruiting
NCT02140242Leukemia, Myelocytic, AcutePhase 32021-09-13Technische Universitt DresdenRecruiting
NCT00474006ACUTE MYELOGENOUS LEUKEMIAPhase 32011-06-10Cooperative Study Group A for HematologyCompleted
NCT00023777LeukemiaPhase 22015-03-06Southwest Oncology GroupCompleted
NCT00589082AMLPhase 32008-01-09Gruppo Italiano Malattie EMatologiche dell'AdultoCompleted
ADCs Cytotoxin
Orange-Red Powder
Shelf Life
≥360 days if stored properly
Room temperature
Store at -20°C
Acute Toxic; Health Hazard
Signal Word
Boiling Point
769.977°C at 760 mmHg
1. Adsorptive Stripping Voltammetric Determination of Low Levels of Daunorubicin
Joseph Wang,* Meng Shan Lin and Vince Villa. ANALYST, SEPTEMBER 1987, VOL. 112
The anthracycline antibiotic daunorubicin is a widely used anticancer drug, owing to its clinical efficacy against a wide range of malignancies. This drug was the first compound to show therapeutic effects in the treatment of leukaemia in man. The cytotoxic activity of daunorubicin against cancerous cells is hampered by dose-related cardiotoxic effects. Conse-quently, a highly sensitive analytical method is essential for the evaluation and administration of this drug. Various analytical methods have been employed for this purpose, including fluorescence, radioimmunoassayn and liquid chromatographic techniques. The complex redox activity of daunorubicin, and related anthracycline antibiotics, was investigated by Rao et aZ. who discussed the redox process in relation to the antineoplastic activity of these drugs. Anthracycline antibiotics contain two electroactive moieties: a reducible quinone group and an oxidisable hydroquinone centre. The reduction of the quinone group was used for polarographic measurements of the structurally similar anthracycline, Adriamycin, down to micromolar concentrations and for measuring the binding of anthracyclines to DNA. Trace amounts of daunorubicin have not yet been determined by voltammetric procedures.
2. Overview on in vitro and in vivo investigations of nanocomposite based cancer diagnosis and therapeutics
A. P. Subramanian, S. K. Jaganathan* and Eko Supriyanto. RSC Adv.,2015, 5, 72638–72652
Nanocomposite made of nano Fe3O4 and polylactide nanofibers loaded with daunorubicin to cause the induction of cell death of leukemia cancer cells was reported. The number of viable cells decreased when treated with the daunorubicin loaded nanocomposite. The cellular uptake was demonstrated by the inter-cellular green fluorescence emitted by the daunorubicin drug. The cell inhibition with the 9.93 *10-7 and 1.99 * 10-6 mol L-1 daunorubicin concentrations in the presence of Fe3O4 nanoparticles or PLA nanofibers produced no significant difference fromthat of the cell treated with daunorubicin alone. However, for daunorubicin concentrations at 9.93 * 10-7 and 1.99 * 10-6 mol L-1, the inhibition rates increased to 31% and 46% for the cell system cultured with daunorubicin and Fe3O4–PLA. Chen et al. developed a poly(lactic acid) (PLA) based nanocomposites for targeted drug delivery of daunorubicin to the leukemia K562 cells.
3. PEG–PLGA–PLL nanoparticles in combination with gambogic acid for reversingmultidrug resistance of K562/A02 cells to daunorubicin
Peipei Xu, Ruju Wang, Jian Li, Jian Ouyanga and Bing Chen*. RSC Adv.,2015, 5,61051–61059
Daunorubicin (DNR) is an effective chemotherapeutic agent which is widely used to treat leukaemia. However, DNR lacks specificity to cancer cells and can induce severe side effects. The development of MDR to DNR also hampered the clinical application of DNR. Therefore, new strategies are needed to overcome drug resistance and selectively deliver chemotherapeutic drugs to the tumour area with the aim of improving therapeutic efficacy.
4. Suitability of porous silicon microparticles for the long-term delivery of redox-active therapeutics
Elizabeth C. Wu, Jennifer S. Andrew, Alex Buyanin, Joseph M. Kinsellac and Michael J. Sailor*. Chem. Commun., 2011, 47, 5699–5701
Therefore, in using pSi as a drug delivery carrier, the redox chemistry of the material with the drug of interest must be considered, especially for molecules that are easily reduced. Anthracyclines such as doxorubicin and daunorubicin have been found to be effective against a wide range of human malignant neoplasms, but they display dose-limiting cardiotoxicity. This toxicity has been attributed to the in vivo reduction of the quinine moiety on the drug to a semiquinone free radical. The semiquinone can disproportionate to the hydroquinone, and further degradation of the compound can occur, potentially generating reactive oxygen radicals such as superoxide or hydroxyl radicals that can lead to DNA damage. Due to their structural similarity to benzoquinone, it is likely that anthracycline drugs will also undergo a redox reaction with a pSi host. Indeed, prior work on daunorubicin-loaded hydrosilylated pSi microparticles reported an uncharacterized degradation reaction in this reductive environment.

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