B4563

Bisantrene dihydrochloride

≥98% (HPLC)

• Synonym(s): Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride, NSC 337766
• Empirical Formula (Hill Notation): C₂₂H₂₂N₈ ·2HCl
• CAS Number: 78186-34-2
• Molecular Weight: 471.39
• MDL number: MFCD01743164
• UNSPSC Code: 12352200
• PubChem Substance ID: 329773240
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: solid
• storage condition: desiccated
• solubility: deionized water: 8 mg/mL
• storage temp.: room temp
• SMILES string: Cl.Cl.C1CN=C(N1)N\N=C\c2c3ccccc3c(\C=N\NC4=NCCN4)c5ccccc25
• InChI: 1S/C22H22N8.2ClH/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22;;/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30);2*1H/b27-13+,28-14+;;
• InChI key: KINULKKPVJYRON-PVNXHVEDSA-N

Description

Application

Bisantrene (NSC 337766), and its derivatives are topoisomerase II poisons and DNA intercalators. It may be used as model compounds to study P-glycoprotein-mediated multiple drug resistance (MDR1). Bisantrene may be used as a Rac1 inhibitor.

Biochem/physiol Actions

Bisantrene dihydrochloride is an antineoplastic agent, MDR1 substrate, DNA intercalator, and topoisomerase II poison. Cancer cells that develop resistance to bisantrene tend to overexpress P-glycoprotein. Bisantrene can be used to select for P-glycoprotein-mediated multiple drug resistance. The data suggest that bisantrene is an excellent substrate for P-glycoprotein.

Bisantrene is an anthracene bishydrazone derivative, which has antitumor activity.

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H302,H400
• Precautionary Statements: P273 - P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Acute 1
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable