 Chemical Structure.png)
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.
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) |
Biological Activity
| Targets | Daunorubicins/Doxorubicins; Topoisomerase II | |
| ln Vitro |
|
|
| ln Vivo |
|
|
| 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 |
|
|
| 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. |
Solubility Data
| Solubility (In Vitro) |
|
|||
| 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. 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 |