9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

Base Information

• Chemical Name: 9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
• CAS No.: 57852-57-0
• Molecular Formula: C26H27NO9.HCl
• Molecular Weight: 533.963
• Hs Code.: 2941906000
• NSC Number: 256439
• DSSTox Substance ID: DTXSID00860722
• ChEMBL ID: CHEMBL1974170
• Mol file: 57852-57-0.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 9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

Chemical Property:

• Vapor Pressure: 4.34E-22mmHg at 25°C
• Melting Point: 183-185°C
• Boiling Point: 725.4 °C at 760 mmHg
• Flash Point: 392.5 °C
• PSA: 176.61000
• LogP: 2.52260
• Storage Temp.: 2-8°C
• Solubility.: ≥26.7 mg/mL in DMSO; insoluble in EtOH; ≥2.39 mg/mL in H2O with ultrasonic
• 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 Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, Xn
• Hazard Codes: T+,Xn
• Statements: 60-61-28-40
• Safety Statements: 53-45-36-22

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=CC=CC=C5C4=O)O)(C(=O)C)O)N)O
• Description: Idarubicin hydrochloride is a derivative of daunorubicin indicated for acute nonlymphocytic leukemia, acute lymphocytic leukemia, and acute myeloid leukemia. Compared with daunorubicin, idarubicin hydrochloride is less cardiotoxic, has milder side effects, is orally active and more potent in experimental leukemias. Idarubicin hydrochloride is also reportedly active in daunorubicin-resistant patients, breast cancer,Hodgkin's and non-Hodgkin's lymphoma.
• Uses: Idarubicin hydrochloride (Idamycin) is used to traet acute myeloid leukemia in adults. Idarubicin HCl is a hydrochloride salt form of Idarubicin which is an anthracycline antibiotic and a DNA topoisomerase II (topo II) inhibitor for MCF-7 cells with IC50 of 3.3 ng/mL Orally active anthracycline; analog of Daunorubicin. Antineoplastic
• Clinical Use: Its primary indication is in acute myeloid leukemia, and it is administered in combination with other antileukemic drug.
• Drug interactions: Potentially hazardous interactions with other drugs Other myelosuppressant medication and radiotherapy: increased risk of myelosuppression. Antipsychotics: avoid concomitant use with clozapine, increased risk of agranulocytosis. Ciclosporin: concentration increased by ciclosporin. Cytotoxics: possible increased cardiotoxicity with trastuzumab. Live vaccines: risk of generalised infections - avoid.

Technology Process of 9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

There total 20 articles about 9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione 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: 95.0%

idarubicin (58957-92-9,58957-91-8,58957-93-0) → idarubicin hydrochloride (57852-57-0,60660-73-3)

Guidance literature:

With hydrogenchloride; In chloroform; isopropyl alcohol;

Reference yield: 80.0%

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin (60660-74-4) → idarubicin hydrochloride (57852-57-0,60660-73-3)

Guidance literature:

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin; With water; sodium hydroxide; at 20 ℃; for 1h;

With hydrogenchloride; In water; pH=8;

Reference yield: 77.0%

C34H35NO10 → idarubicin hydrochloride (57852-57-0,60660-73-3)

Guidance literature:

C₃₄H₃₅NO₁₀; With palladium(II) hydroxide; In tetrahydrofuran; at 40 ℃; for 4h;

With hydrogenchloride; In methanol; diethyl ether; pH=3;

upstream raw materials:

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose

(7S,9S)-idarubicinone

1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose

Downstream raw materials:

(+)-4-demethoxyadriamycin hydrochloride

4-demethoxy-11-deoxydaunorubicin

(7S,9S)-idarubicinone

8-Acetyl-6,11-dihydroxy-naphthacene-5,12-dione

Refernces

• 1、 -. "Preparation method for idarubicin hydrochloride". Paragraph 0042; 0043. . Retrieved 2018/04/02.
• 2、 -. "METHOD OF PRODUCING 4-DEMETHOXYDAUNORUBICIN". Page/Page column 9. . Retrieved 2012/11/08.