Idarubicin

Base Information

• Chemical Name: Idarubicin
• CAS No.: 58957-92-9
• Molecular Formula: C26H27NO9
• Molecular Weight: 497.502
• UNII: ZRP63D75JW
• DSSTox Substance ID: DTXSID7023142
• Nikkaji Number: J32.515E
• Wikipedia: Idarubicin
• Wikidata: Q1063862
• NCI Thesaurus Code: C562
• RXCUI: 5650
• Pharos Ligand ID: LAYGFF7BPKK9
• Metabolomics Workbench ID: 43394
• ChEMBL ID: CHEMBL1117
• Mol file: 58957-92-9.mol

Synonyms:4 Demethoxydaunorubicin;4 Desmethoxydaunorubicin;4-Demethoxydaunorubicin;4-Desmethoxydaunorubicin;Hydrochloride, Idarubicin;Idarubicin;Idarubicin Hydrochloride;IMI 30;IMI-30;IMI30;NSC 256439;NSC-256439;NSC256439

Chemical Property of Idarubicin

Chemical Property:

• Refractive Index: 1.6000 (estimate)
• Boiling Point: 725.435 °C at 760 mmHg
• PKA: pKa 4.73± 0.21 (Uncertain)
• Flash Point: 392.529 °C
• PSA: 176.61000
• Density: 1.565 g/cm³
• LogP: 1.72060
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 497.16858144
• Heavy Atom Count: 36
• Complexity: 912

Purity/Quality:

99%, ^*data from raw suppliers

Idarubicin United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 60-61-28-40
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=CC=CC=C5C4=O)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=CC=CC=C5C4=O)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: Phase 3 Randomized, Controlled Study of Blinatumomab Alternating With Low-intensity Chemotherapy Versus Standard of Care for Older Adults With Newly Diagnosed Philadelphia-negative B-cell Precursor Acute Lymphoblastic Leukemia With Safety Run-in (Golden State Study)
• Recent NIPH Clinical Trials: A clinical trial of risk-stratification and gemtuzumab ozogamicin combined post-induction chemotherapy for children with AML
• Uses: Antineoplastic.
• Indications: Idarubicin (Idamycin) differs from its parent compound, daunorubicin, by the absence of the methoxy group in the anthracycline ring structure. Its mechanisms of action and resistance are similar to those of doxorubicin and daunorubicin; however, it is more lipophilic and more potent than these other anthracyclines. Idarubicin undergoes extensive hepatic metabolism and biliary excretion. Adverse reactions of idarubicin are similar to those of its congeners.

Technology Process of Idarubicin

There total 13 articles about Idarubicin 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:

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin (60660-74-4) → idarubicin (58957-92-9,58957-91-8,58957-93-0)

Guidance literature:

With sodium hydroxide; In water; for 0.5h; Ambient temperature;

Reference yield:

4-demethoxy-3'-N3-daunorubicin (1403872-37-6) → idarubicin (58957-92-9,58957-91-8,58957-93-0)

Guidance literature:

4-demethoxy-3'-N₃-daunorubicin; With triphenylphosphine; In tetrahydrofuran;

With ammonia; In tetrahydrofuran;

Reference yield:

daunomycin hydrochloride (23541-50-6) → idarubicin (58957-92-9,58957-91-8,58957-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate; triflic azide / dichloromethane; water; methanol

2.1: potassium iodide; magnesium chloride / tetrahydrofuran / 1.5 h / 40 °C

2.2: pH 2.5 / Cooling with ice

3.1: N-ethyl-N,N-diisopropylamine; pyridine / dmap / 1 h / 0 - 20 °C

4.1: triethylammonium formate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 8 h / 50 °C / Inert atmosphere

5.1: triphenylphosphine / tetrahydrofuran

With pyridine; triflic azide; triethylammonium formate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; potassium iodide; magnesium chloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

(-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin

(7S,9S)-idarubicinone

2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranosyl p-nitrobenzoate

Downstream raw materials:

idarubicin hydrochloride

Idarubicinol

C₂₃H₂₂O₇

(7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<1-(R)-hydroxyethyl>-5,12-naphthacenedione hydrochloride

Refernces

An improved route to 4 demethoxydaunomycinone. A-ring functionalization and resolution studies of tetracyclic precursors

10.1021/ja00344a031

The research focuses on the development of an improved synthetic route to 4-demethoxydaunomycinone (24), a significant intermediate in the synthesis of the antineoplastic drug 4-demethoxydaunomycin. The study explores the functionalization of the A-ring of tetracyclic precursors, particularly the introduction of the cis-7,9-diol functionality and the resolution of racemic 4-demethoxy-7-deoxydaunomycinone (16) into its enantiomers using Enders' hydrazine reagent. Key chemicals involved in the research include 4-demethoxy-7,9-dideoxydaunomycinone (4), its dimethyl ether (5), various reagents such as perchloric acid, acetic anhydride, m-chloroperbenzoic acid, and sodium hydroxide for the functionalization steps, and Enders' hydrazine reagent for the resolution process. The research also involves the synthesis and characterization of several intermediate compounds, such as enol acetate 7, epoxy acetate 12, hydroxy ketones 16 and 19, and the 7-bromo derivatives 21 and 22, which are crucial for achieving the desired functionalization and resolution. The study provides detailed procedures and conditions for the synthesis of these compounds, contributing to the development of a practical and efficient route for the preparation of 4-demethoxydaunomycinone in multigram quantities.

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