Daunorubicin

Base Information

• Chemical Name: Daunorubicin
• CAS No.: 20830-81-3
• Deprecated CAS: 1407-15-4,23942-76-9,149541-57-1,11006-54-5,11048-29-6,28020-80-6,27576-81-4,182250-71-1,11006-54-5,11048-29-6,149541-57-1,23942-76-9,28020-80-6
• Molecular Formula: C27H29NO10
• Molecular Weight: 527.528
• European Community (EC) Number: 245-723-4,244-069-7
• NSC Number: 756717
• UNII: ZS7284E0ZP
• DSSTox Substance ID: DTXSID7022883
• Nikkaji Number: J3.149F
• Wikipedia: Daunorubicin
• Wikidata: Q411659
• NCI Thesaurus Code: C62091
• RXCUI: 3109
• Pharos Ligand ID: 5TACXUKUJFYP
• Metabolomics Workbench ID: 27933
• ChEMBL ID: CHEMBL178
• Mol file: 20830-81-3.mol

Synonyms:(+)-Daunomycin;AI3-52942;Acetyladriamycin;BRN 1445583;CCRIS 914;Daunarubicinum;Daunamycin;Cerubidin;DaunoXome;Daunomycin;Daunorrubicina;UNII-ZS7284E0ZP;

Chemical Property of Daunorubicin

Chemical Property:

• Appearance/Colour: Orange-red powder.
• Melting Point: 155 °C
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 769.977 °C at 760 mmHg
• PKA: pKa 4.92±0.16(H2O t=25±0.5 I=0.03) (Uncertain)
• Flash Point: 419.467 °C
• PSA: 185.84000
• Density: 1.554 g/cm³
• LogP: 1.72920
• Solubility.: ≥83.33 mg/mL in DMSO
• Water Solubility.: Soluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 527.17914612
• Heavy Atom Count: 38
• Complexity: 960

Purity/Quality:

98%,99%, ^*data from raw suppliers

Daunorubicin >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 3249:
• Hazard Codes: 3249:
• Statements: 3249:

MSDS Files:

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antineoplastic Agents
• 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
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](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
• Recent ClinicalTrials: Isatuximab in Combination With Chemotherapy in Pediatric Patients With Relapsed/Refractory Acute Lymphoblastic Leukemia or Acute Myeloid Leukemia
• Recent EU Clinical Trials: Venetoclax plus Azacitidine versus Standard intensive Chemotherapy for Patients with newly diagnosed Acute Myeloid Leukemia (AML) and NPM1 Mutations eligible for intensive Treatment (VINCENT)
• Recent NIPH Clinical Trials: Post remission therapy with arsenic trioxide and gemtuzumab ozogamicin in acute promylocytic leukemia (JALSG APL212)
• Uses: Daunorubicin hydrochloride USP (Cerubidine) is used to traet acute lymphocytic and granulocytic leukemia; lymphomas. antineoplastic Oncology
• Indications: Daunorubicin (Cerubidine) is used to treat acute leukemias, while its structural analogue, doxorubicin (Adriamycin) is extensively employed against a broad spectrum of cancers. Although the two drugs have similar pharmacological and toxicological properties, doxorubicin is more potent against most animal and human tumors and will be discussed in greater detail.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Antineoplastic agent:Acute leukaemiasHIV-related Kaposi’s Sarcoma
• Drug interactions: Potentially hazardous interactions with other drugsAntipsychotics: avoid with clozapine due to risk of agranulocytosis.Cytotoxics: possible increased cardiotoxicity with trastuzumab - avoid for up to 28 weeks after stopping trastuzumab.Avoid with live vaccines.

Technology Process of Daunorubicin

There total 20 articles about Daunorubicin 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: 83.0%

→ DNR (20830-81-3) + N-[4-Methoxy-5-nitro-2-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate)benzyloxycarbonyl]daunorubicin

Guidance literature:

Reference yield:

Daunorubicin+ Mitoxantrone → DNR (20830-81-3) + novantrone (65271-80-9,70945-62-9)

Guidance literature:

In water-d2; at 44.85 ℃; pH=7.1; Equilibrium constant;

DOI:10.1016/j.molstruc.2004.05.014

Reference yield:

daunomycin hydrochloride (23541-50-6) → DNR (20830-81-3)

Guidance literature:

With triethylamine; In methanol; dichloromethane; water;

upstream raw materials:

(8S-cis)-8-acetyl-10-<(3-amino-2,3,6-trideoxy-α-L-lyxohexopyranosyl)oxy>-6a,7,8,9,10,10a-hexahydro-5,8,12-trihydroxy-1-methoxy-6,11-naphthacenedione

(S)-2-Amino-4-methyl-pentanoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide

N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-β-D-glucopyranosyl carbamate

N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-β-D-galactopyranosyl carbamate

Downstream raw materials:

3'-N-daunorubicin

C₃₇H₄₃Cl₂N₄O₁₁P*ClH

C₃₈H₄₅Cl₂N₄O₁₁P*ClH

C₃₇H₄₂BrCl₂N₄O₁₁P*ClH

Refernces

• 1、 Kratz, Felix,Beyer, Ulrich,Schumacher, Peter,Krueger, Michael,Zahn, Heike,Roth, Thomas,Fiebig, Heinz H.,Unger, Clemens. "Synthesis of new maleimide derivatives of daunorubicin and biological activity of acid labile transferrin conjugates". . p. 617 - 622. Retrieved 1997.
• 2、 -. "Block copolymers for stable micelles". Page/Page column. . Retrieved 2013/11/19.
• 3、 -. "METHOD OF DERIVATISING AN ANALYTE FOR SUBSEQUENT DETECTION THROUGH A NUCLEIC ACID BASED SENSOR". . . Retrieved 2010/04/30.