2-{2-[(10-{[2-(4,5-dihydro-1H-imidazol-2-yl)hydrazin-1-ylidene]methyl}anthracen-9-yl)methylidene]hydrazin-1-yl}-4,5-dihydro-1H-imidazole dihydrochloride

• ChemBase ID: 154672
• Molecular Formular: C22H24Cl2N8
• Molecular Mass: 471.38556
• Monoisotopic Mass: 470.15009817
• SMILES: c1cc2c(c3c(c(c2cc1)/C=N/NC1=NCCN1)cccc3)/C=N/NC1=NCCN1.Cl.Cl
• Canonical SMILES: C1CN=C(N1)N/N=C/c1c2ccccc2c(c2c1cccc2)/C=N/NC1=NCCN1.Cl.Cl
• InChI: 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
• InChIKey: KINULKKPVJYRON-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(10-{[2-(4,5-dihydro-1H-imidazol-2-yl)hydrazin-1-ylidene]methyl}anthracen-9-yl)methylidene]hydrazin-1-yl}-4,5-dihydro-1H-imidazole dihydrochloride
• IUPAC Traditional name: 2-{2-[(10-{[2-(4,5-dihydro-1H-imidazol-2-yl)hydrazin-1-ylidene]methyl}anthracen-9-yl)methylidene]hydrazin-1-yl}-4,5-dihydro-1H-imidazole dihydrochloride
• Synonyms: Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride; NSC 337766; Bisantrene dihydrochloride

Database IDs

• CAS Number: 78186-34-2
• MDL Number: MFCD01743164
• PubChem SID: 162248810
• PubChem CID: 6917792

CALCULATED PROPERTIES

• Acid pKa: 19.764172
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.5034872
• LogD (pH = 7.4): 2.5721939
• Log P: 2.5997148
• Molar Refractivity: 140.3186 cm^3
• Polarizability: 46.08328 Å^3
• Polar Surface Area: 97.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: deionized water: soluble8 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H400
• GHS Precautionary statements: P273
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H22N8 ·2HCl

DETAILS

Sigma Aldrich - B4563

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.1