Amrubicin hydrochloride

Base Information

• Chemical Name: Amrubicin hydrochloride
• CAS No.: 110311-30-3
• Molecular Formula: C25H25 N O9 . Cl H
• Molecular Weight: 519.9282
• UNII: EUL6MP8FZW
• DSSTox Substance ID: DTXSID10911577
• Wikidata: Q27277373
• NCI Thesaurus Code: C47948
• ChEMBL ID: CHEMBL481958
• Mol file: 110311-30-3.mol

Synonyms:(+)-(7S,9S)-9-acetyl-9-amino-7-((2-deoxy-beta-d-erythro-pentopyranosyl)oxy)-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride;(7S,9S)-9-acetyl-9-amino-7-((2-deoxy-beta-D-erythro-pentopyranosyl)oxy)-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione hydrochloride;amrubicin;amrubicin hydrochloride;SM 5887;SM-5887

Chemical Property of Amrubicin hydrochloride

Chemical Property:

• Vapor Pressure: 1.26E-21mmHg at 25°C
• Melting Point: 145-151°
• Boiling Point: 717.8°C at 760 mmHg
• Flash Point: 387.9°C
• PSA: 176.61000
• LogP: 2.13410
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 519.1296091
• Heavy Atom Count: 36
• Complexity: 881

Purity/Quality:

99% ^*data from raw suppliers

Amrubicinhydrochloride 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)OC5CC(C(CO5)O)O)N.Cl
• Isomeric SMILES: CC(=O)[C@]1(C[C@@H](C2=C(C1)C(=C3C(=C2O)C(=O)C4=CC=CC=C4C3=O)O)O[C@H]5C[C@@H]([C@@H](CO5)O)O)N.Cl
• Recent ClinicalTrials: Amrubicin Study for Elderly Patients With Extensive-disease Small-cell Lung Cancer (ED-SCLC)
• Recent EU Clinical Trials: A Randomized, Open-Label, Multinational Phase 3 Trial Comparing Amrubicin Versus Topotecan in Patients With Extensive or Limited and Sensitive or Refractory Small Cell Lung Cancer After Failure of First-Line Chemotherapy
• Recent NIPH Clinical Trials: None
• Description: small and small-cell lung cancers. Amrubicin, a completely synthetic anthracycline derivative, mediates its growth inhibitory action via topoisomerase II inhibition. It is activated in viva by the formation of its 13-OH metabolite, amrubicinol, via reaction with carbonyl reductase. In contrast to doxorubicin and daunorubicin whose metabolites are inactive in the blood, amrubicinol is 10-100 fold more cytotoxic than amrubicin. In phase II clinical trials, amrubicin showed antitumor activity against non-small-cell lung cancers (response rate exceeding 20%) and against untreated extensive stage small-cell-lung cancers (response rate 78.8%). Amrubicin demonstrated a smaller distribution-volume, a shorter half-life in mice and also less chronic cardiotoxicity in preclinical studies compared to doxorubicin. Amrubicin was generally well tolerated with major adverse events being anaemia, leucopenia, thrombocytopenia and neutropenia.

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