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Daunorubicin HCl (Daunomycin)

Alias: Daunomycin HCl; RP 13057; Rubidomycin; RP-13057; RP13057; Daunomycin hydrochloride; daunomycin HCl; daunorubidomycine; US trade names: Cerubidine; Rubidomycin; Foreign brand names: Cerubidin; Daunoblastin; Daunoblastina; Ondena; Rubilem; Abbreviations: DNM; DNR; DRB; Code names: FI6339; RP13057
Cat No.:V1400 Purity: ≥98%
Daunorubicin HCl (Daunomycin; RP-13057; Rubidomycin; Ondena; Rubilem; DNM; DNR; DRB; FI6339; RP13057), the hydrochloride salt of daunorubicin, is an anthracycline analog and a topoisomerase II inhibitor which is approved for use as an antibiotic and chemotherapeutic drug.
Daunorubicin HCl (Daunomycin)
Daunorubicin HCl (Daunomycin) Chemical Structure CAS No.: 23541-50-6
Product category: Topoisomerase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
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1g
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Other Forms of Daunorubicin HCl (Daunomycin):

  • Daunorubicin citrate; RP 13057(citrate)
  • Daunorubicin
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Daunorubicin HCl (Daunomycin; RP-13057; Rubidomycin; Ondena; Rubilem; DNM; DNR; DRB; FI6339; RP13057), the hydrochloride salt of daunorubicin, is an anthracycline analog and a topoisomerase II inhibitor which is approved for use as an antibiotic and chemotherapeutic drug.

Biological Activity I Assay Protocols (From Reference)
Targets
Daunorubicins/Doxorubicins; Topoisomerase II
ln Vitro

Daunorubicin hydrochloride (0-256 μg/mL, 30 min) inhibits the synthesis of DNA and RNA in Ehrlich ascites tumor cells, both sensitive and resistant[2].
Daunorubicin hydrochloride (7 nM-1.9 μM, 72 h) exhibits chemosensitivity in Molt-4 cells and L3.6 cells[3][4].
Daunorubicin hydrochloride (0.4 μM, 48 h) causes necrosis and apoptosis in L3.6 cells[4].
Daunorubicin hydrochloride (0.4 μM, 120 min) causes ROS generation in L3.6 cells[4].
Daunorubicin hydrochloride (2 μM, 24 h) induces autophagy in K562 cells (myeloid cell line)[6].

ln Vivo
Daunorubicin hydrochloride (three intravenous injections at 48-hour intervals, at a dose of 3 mg/kg). causes rats to become nephrotoxic and cardiotoxic[5].
Daunorubicin hydrochloride (intraperitoneal injection, 10 mg/kg) causes sister chromatid exchanges in mice[7].
Enzyme Assay
Inhibition of DNA and RNA synthesis by daunorubicin in sensitive and resistant Ehrlich ascites tumor cells in vitro [2].
Cell Assay
Cell Line: Molt-4 cells (a human T-lymphoblastic leukemia cell line), L3.6 cells (metastatic human pancreatic cell line)
Concentration: 7 nM-1.9 μM
Incubation Time: 72 h
Result: Inhibited cell viability with IC50 values of 40 nM (Molt-4) and 400 nM (L3.6).
Animal Protocol
Male Sprague-Dawley rats eight weeks of age are employed. Two more weeks are spent acclimating and keeping the animals in quarantine before the experiments begin. Day 0: A single intravenous injection of Daunorubicin (3 mg/kg) is given to each animal. To achieve an accumulative dose of 9 mg/kg, daunorubicin is given in three equal injections spaced 48 hours apart over the course of one week. It is well known that this dosage will cause nephrotoxicity and cardiotoxicity. As a control, age-matched rats (group Control; n=5) are injected with corresponding volumes of 0.9% NaCl. Twenty-two DNR-treated rats were split into two groups at random and given either a vehicle (group Daunorubicin; n = 12) or Telmisartan (10 mg/kg/day; group Daunorubicin+Telmisartan; n = 10). A prior report is used to determine the dosage of Telmisartan. Telmisartan is administered for 5 weeks after stopping Daunorubicin administration, commencing on the same day as Daunorubicin administration (6 weeks total). The length of the study was selected based on earlier reports. Rats are individually housed in metabolic cages on day 41, and urine samples are collected every 24 hours to measure protein concentrations and body weight (BW). Rats are sacrificed and kidney tissue is taken for semi-quantitative immunoblotting and immunohistochemical investigations after the six-week study period.
Rats known as Sprague-Dawley
References

[1]. Activity of topoisomerase inhibitors daunorubicin, idarubicin, and aclarubicin in the Drosophila Somatic Mutation and Recombination Test. Environ Mol Mutagen. 2004;43(4):250-7.

[2]. Inhibition of DNA and RNA synthesis by daunorubicin in sensitive and resistant Ehrlich ascites tumor cells in vitro. Cancer Res. 1972 Jun;32(6):1307-14.

[3]. Melanin inhibits cytotoxic effects of Doxorubicin and Daunorubicin in MOLT 4 cells. Pigment Cell Res. 2003 Aug;16(4):351-4.

[4]. An effective in vitro antitumor response against human pancreatic carcinoma with paclitaxel and Daunorubicin by induction of both necrosis and apoptosis. Anticancer Res. 2004 Sep-Oct;24(5A):2617-26.

[5]. Telmisartan prevents the progression of renal injury in daunorubicin rats with the alteration of angiotensin II and endothelin-1 receptor expression associated with its PPAR-γ agonist actions. Toxicology. 2011 Jan 11;279(1-3):91-9.

[6]. MiR-15a-5p Confers Chemoresistance in Acute Myeloid Leukemia by Inhibiting Autophagy Induced by Daunorubicin. Int J Mol Sci. 2021 May 13;22(10):5153.

[7]. Doxorubicin suppresses chondrocyte differentiation by stimulating ROS production. Eur J Pharm Sci. 2021 Dec 1;167:106013.

Additional Infomation
Daunorubicin Hydrochloride can cause developmental toxicity according to state or federal government labeling requirements.
Daunorubicin hydrochloride appears as orange-red powder. Thin red needles decomposing at 188-190 °C. An anti-cancer drug.
Daunorubicin hydrochloride is an anthracycline.
Daunorubicin Hydrochloride is the hydrochloride salt of an anthracycline antineoplastic antibiotic with therapeutic effects similar to those of doxorubicin. Daunorubicin exhibits cytotoxic activity through topoisomerase-mediated interaction with DNA, thereby inhibiting DNA replication and repair and RNA and protein synthesis.
A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H29NO10.HCL
Molecular Weight
563.98
Exact Mass
563.155
Elemental Analysis
C, 57.50; H, 5.36; Cl, 6.29; N, 2.48; O, 28.37
CAS #
23541-50-6
Related CAS #
1884557-85-0; 20830-81-3; 371770-68-2 (citrate); 23541-50-6 (HCl)
PubChem CID
62770
Appearance
Red solid powder
Boiling Point
770ºC at 760 mmHg
Melting Point
188 - 190ºC
Flash Point
419.5ºC
Vapour Pressure
6.99E-26mmHg at 25°C
LogP
2.531
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
39
Complexity
960
Defined Atom Stereocenter Count
6
SMILES
Cl[H].O([C@@]1([H])C([H])([H])[C@@]([H])([C@@]([H])([C@]([H])(C([H])([H])[H])O1)O[H])N([H])[H])[C@]1([H])C2C(=C3C(C4C(=C([H])C([H])=C([H])C=4C(C3=C(C=2C([H])([H])[C@@](C(C([H])([H])[H])=O)(C1([H])[H])O[H])O[H])=O)OC([H])([H])[H])=O)O[H]
InChi Key
GUGHGUXZJWAIAS-QQYBVWGSSA-N
InChi Code
InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
Chemical Name
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
Synonyms
Daunomycin HCl; RP 13057; Rubidomycin; RP-13057; RP13057; Daunomycin hydrochloride; daunomycin HCl; daunorubidomycine; US trade names: Cerubidine; Rubidomycin; Foreign brand names: Cerubidin; Daunoblastin; Daunoblastina; Ondena; Rubilem; Abbreviations: DNM; DNR; DRB; Code names: FI6339; RP13057
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 50~100 mg/mL (88.7~177.3 mM)
Water: ~100 mg/mL (177.3 mM)
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.69 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.69 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: Saline: 30 mg/mL


Solubility in Formulation 4: 33.33 mg/mL (59.10 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7731 mL 8.8656 mL 17.7311 mL
5 mM 0.3546 mL 1.7731 mL 3.5462 mL
10 mM 0.1773 mL 0.8866 mL 1.7731 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
MYELOMATCH: A Screening Study to Assign People With Myeloid Cancer to a Treatment Study or Standard of Care Treatment Within myeloMATCH (MyeloMATCH Screening Trial)
CTID: NCT05564390
Phase: Phase 2    Status: Recruiting
Date: 2024-11-29
BLAST MRD AML-1: BLockade of PD-1 Added to Standard Therapy to Target Measurable Residual Disease in Acute Myeloid Leukemia 1- A Randomized Phase 2 Study of Anti-PD-1 Pembrolizumab in Combination With Intensive Chemotherapy as Frontline Therapy in Patients With Acute Myeloid Leukemia
CTID: NCT04214249
Phase: Phase 2    Status: Active, not recruiting
Date: 2024-11-26
Testing the Effects of Novel Therapeutics for Newly Diagnosed, Untreated Patients With High-Risk Acute Myeloid Leukemia (A MyeloMATCH Treatment Trial)
CTID: NCT05554406
Phase: Phase 2    Status: Recruiting
Date: 2024-11-26
Comparing Cytarabine + Daunorubicin Therapy Versus Cytarabine + Daunorubicin + Venetoclax Versus Venetoclax + Azacitidine in Younger Patients With Intermediate Risk AML (A MyeloMATCH Treatment Trial)
CTID: NCT05554393
Phase: Phase 2    Status: Recruiting
Date: 2024-11-26
Combination Chemotherapy With or Without Bortezomib in Treating Younger Patients With Newly Diagnosed T-Cell Acute Lymphoblastic Leukemia or Stage II-IV T-Cell Lymphoblastic Lymphoma
CTID: NCT02112916
Phase: Phase 3    Status: Active, not recruiting
Date: 2024-11-13
View More

Combination Chemotherapy in Treating Young Patients With Newly Diagnosed High-Risk B Acute Lymphoblastic Leukemia and Ph-Like TKI Sensitive Mutations
CTID: NCT02883049
Phase: Phase 3    Status: Active, not recruiting
Date: 2024-11-13


Response-Based Chemotherapy in Treating Newly Diagnosed Acute Myeloid Leukemia or Myelodysplastic Syndrome in Younger Patients With Down Syndrome
CTID: NCT02521493
Phase: Phase 3    Status: Active, not recruiting
Date: 2024-11-07
Venetoclax and a Pediatric-Inspired Regimen for the Treatment of Newly Diagnosed B Cell Acute Lymphoblastic Leukemia
CTID: NCT05157971
Phase: Phase 1    Status: Recruiting
Date: 2024-10-26
Inotuzumab Ozogamicin and Frontline Chemotherapy in Treating Young Adults With Newly Diagnosed B Acute Lymphoblastic Leukemia
CTID: NCT03150693
Phase: Phase 3    Status: Suspended
Date: 2024-10-26
Inotuzumab Ozogamicin and Post-Induction Chemotherapy in Treating Patients With High-Risk B-ALL, Mixed Phenotype Acute Leukemia, and B-LLy
CTID: NCT03959085
Phase: Phase 3    Status: Recruiting
Date: 2024-10-22
Bortezomib and Sorafenib Tosylate in Treating Patients With Newly Diagnosed Acute Myeloid Leukemia
CTID: NCT01371981
Phase: Phase 3    Status: Active, not recruiting
Date: 2024-10-22
A Study to Compare Standard Chemotherapy to Therapy With CPX-351 and/or Gilteritinib for Patients With Newly Diagnosed AML With or Without FLT3 Mutations
CTID: NCT04293562
Phase: Phase 3    Status: Active, not recruiting
Date: 2024-10-22
Combination Chemotherapy in Treating Young Patients With Newly Diagnosed T-Cell Acute Lymphoblastic Leukemia or T-cell Lymphoblastic Lymphoma
CTID: NCT00408005
Phase: Phase 3    Status: Active, not recruiting
Date: 2024-10-21
Imatinib Mesylate and Combination Chemotherapy in Treating Patients With Newly Diagnosed Philadelphia Chromosome Positive Acute Lymphoblastic L
Dutch-Belgian pediatric AML protocol for children with newly diagnosed acute myeloid leukemia, based on the NOPHO-AML 2004 study
CTID: null
Phase: Phase 3    Status: Completed
Date: 2010-05-04
A Phase I/II study of clofarabine in combination with cytarabine and liposomal daunorubicin in children with relapsed/refractory pediatric AML
CTID: null
Phase: Phase 1, Phase 2    Status: Completed
Date: 2009-07-30
A Randomized, Risk and Age Adapted Comparison of the Dose-Dense Regimen S-HAM (sequential high dose cytosine arabinoside and mitoxantrone) versus Standard Double Induction for Initial Chemotherapy of Adult Patients with Acute Myeloid Leukemia
CTID: null
Phase: Phase 3    Status: Completed
Date: 2009-03-10
Phase I Dose Escalation Study of Clofarabine and Liposomal Daunorubicin in Childhood and Adolescent AML
CTID: null
Phase:    Status: Completed
Date: 2009-02-10
Etude multicentrique de phase III randomisée ouverte testant l’efficacité du gemtuzumab ozogamycin (MYLOTARG®) en association avec la chimiothérapie intensive chez les patients de 18 à 60 ans atteints de leucémie aiguë myéloblastique (LAM) avec cytogénétique intermédiaire.
CTID: null
Phase: Phase 3    Status: Completed
Date: 2007-08-16
''Geriatric assessment adapted'' therapy for the treatment of Ph-negative Acute lymphoblastic Leukemia in elder patients.
CTID: null
Phase: Phase 2    Status: Completed
Date: 2007-05-22
A PHASE III STUDY OF THE ADDITION OF GEMTUZUMAB OZOGAMICIN (MYLOTARG®) DURING INDUCTION THERAPY VERSUS STANDARD INDUCTION WITH DAUNOMYCIN AND CYTOSINE ARABINOSIDE FOLLOWED BY CONSOLIDATION AND SUBSEQUENT RANDOMIZATION TO POST-CONSOLIDATION THERAPY WITH GEMTUZUMAB OZOGAMICIN (MYLOTARG®) OR NO ADDITIONAL THERAPY FOR PATIENTS UNDER AGE 61 WITH PREVIOUSLY UNTREATED DE NOVO ACUTE MYELOID LEUKAEMIA (AML)
CTID: null
Phase: Phase 3    Status: Prematurely Ended
Date: 2007-04-10
Etude de phase 3 comparant une chimiothérapie d'induction séquentielle systématique à une chimiothérapie d'induction séquentielle conditionnelle chez des patients atteints d'une Leucémie Aigüe Myéloïde du groupe CBF
CTID: null
Phase: Phase 3    Status: Completed
Date: 2007-01-22
Multizentrische Therapieoptimierungsstudie AML-BFM 2004 zur Behandlung der akuten myeloischen Leukämien bei Kindern und Jugendlichen
CTID: null
Phase: Phase 3, Phase 4    Status: Completed
Date: 2006-11-26
Curative and palliative treatment of adults aged > 60 years with AML.A randomised trial by OSHO on the role of (1) early intensification {OSHO protocol} vs. common standard arm of German AML Intergroup Study, (2) allografting as consolidative immunotherapy vs. a second consolidation course in elderly patients,(3) prospective evaluation of the decision between curative and palliative treatment-intention.
CTID: null
Phase: Phase 3    Status: Ongoing
Date: 2006-03-08
Evaluation of the intensification of post-remissional therapy in the treatment of high-risks adult Acute Lymphoblastic Leukemia and monitoring of the minimal residual disease
CTID: null
Phase: Phase 3    Status: Completed
Date: 2004-11-08
International collaborative treatment protocol for children and adolescents with acute lymphoblastic leukemia
CTID: null
Phase: Phase 3    Status: Ongoing, Completed
Date:

Biological Data
  • Treatment with daunorubicin increases autophagy in K562 cells. Int J Mol Sci . 2021 May 13;22(10):5153.
  • miR-15a-5p inhibits autophagy induced by daunorubicin. Int J Mol Sci . 2021 May 13;22(10):5153.
  • miR-15a-5p decreases the downregulation of cell growth by daunorubicin. Int J Mol Sci . 2021 May 13;22(10):5153.
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