Daunorubicin hydrochloride

Base Information

• Chemical Name: Daunorubicin hydrochloride
• CAS No.: 23541-50-6
• Molecular Formula: C27H29NO10^.HCl
• Molecular Weight: 563.989
• Hs Code.: 29419059
• European Community (EC) Number: 245-723-4
• NSC Number: 301724,257457,249333,83142,304419,82151
• UN Number: 2811
• NCI Thesaurus Code: C1583
• RXCUI: 81992
• ChEMBL ID: CHEMBL158918
• Mol file: 23541-50-6.mol

Synonyms:5,12-Naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-,hydrochloride, (8S,10S)- (9CI);Cerubidine;Daunoblastin;Daunomycin chlorohydrate;NDC0082-4155;Ondena;RP 13057 hydrochloride;Rubidomycin hydrochloride;

Chemical Property of Daunorubicin hydrochloride

Chemical Property:

• Appearance/Colour: dark red crystals
• Vapor Pressure: 6.99E-26mmHg at 25°C
• Melting Point: 190°C (dec)
• Boiling Point: 770 °C at 760 mmHg
• Flash Point: 419.5 °C
• PSA: 185.84000
• Density: 1.554 g/cm³
• LogP: 2.53120
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: Freely soluble in water and in methanol, slightly soluble in alcohol, practically insoluble in acetone.
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 563.1558238
• Heavy Atom Count: 39
• Complexity: 960
• Transport DOT Label: Poison

Purity/Quality:

99.5%, ^*data from raw suppliers

Daunorubicin HCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-40-42/43-36/37/38-20/21/22
• Safety Statements: 22-36/37-45-37/39-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl
• Isomeric SMILES: CC1C(C(CC(O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O.Cl
• Recent ClinicalTrials: Selinexor With Combination With Induction/Consolidation Therapy in Acute Myeloid Leukemia Patients
• Recent EU Clinical Trials: A Phase 1B/2 Study To Evaluate The Safety And Efficacy of PF-04449913, An Oral Hedgehog Inhibitor, In Combination With Intensive Chemotherapy, Low Dose ARA-C Or Decitabine In Patients With Acute Myeloid Leukemia Or High-Risk Myelodysplastic Syndrome
• Description: Daunorubicin HCl (23541-50-6) is an antitumor antibiotic used in the treatment of acute myeloid leukemias.1?Induces DNA damage by intercalation.2?Induces apoptosis in a variety of cell lines.3?Inhibition of autophagy with chloroquine enhances daunorubicin-induced apoptosis in K562 cells.4?Cell permeable.
• Uses: Anthracycline antibiotic related to the rhodomycins. Antineoplastic Antineoplastic;DNA intercaling anti-neoplastic LD50 in mice 26 mg/kg A DNA intercalator which may suppress acute leukemia proliferation
• Therapeutic Function: Antineoplastic
• Clinical Use: Daunorubicin is administered IV at a dose of 45 mg/m2 for the treatment of lymphocytic and nonlymphocytic leukemia.

Technology Process of Daunorubicin hydrochloride

There total 15 articles about Daunorubicin hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

→ daunomycin hydrochloride (23541-50-6)

Guidance literature:

Reference yield:

4-Amino-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride (110925-32-1) → daunomycin hydrochloride (23541-50-6) + 4-aminobenzohydrazide (5351-17-7)

Guidance literature:

With water; at 37 ℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;

DOI:10.1007/BF00758626

Reference yield:

4-Hydroxy-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride (66996-57-4) → daunomycin hydrochloride (23541-50-6) + 4-hydroxybenzoic acid hydrazide (5351-23-5)

Guidance literature:

With water; at 37 ℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;

DOI:10.1007/BF00758626

upstream raw materials:

Benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

Nicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

4-Amino-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

Downstream raw materials:

4-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride

3'-deamino-3'-morpholino-13,13-dihydrodaunorubicin

3'-deamino-3'-morpholinodaunoribicin

3'-deamino-3'-(3-cyano-4-morpholinyl)-13-dihydrodaunorubicin

Refernces

• 1、 -. "Coumarin and related aromatic-based polymeric prodrugs". . . Retrieved 2008/06/13.
• 2、 Boivin, Jean,Montagnac, Alain,Monneret, Claude,Pais, Mary. "HEMISYNTHESE DE NOUVEAUX GLICOSIDES ANALOGUES DE LA DAUNORUBICINE". . p. 223 - 242. Retrieved 2007/10/02.