Skip to Content
Merck

Key Documents

View All Documentation

B4563

Bisantrene dihydrochloride

≥98% (HPLC)

Synonym(s):

Bis((4,5-dihydro-1H-imidazol-2-yl)hydrazone)-9,10-anthracenedicarboxaldehyde dihydrochloride, NSC 337766

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C22H22N8 ·2HCl
CAS Number:
78186-34-2
Molecular Weight:
471.39
NACRES:
NA.77
PubChem Substance ID:
329773240
UNSPSC Code:
12352200
MDL number:
MFCD01743164
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
Storage condition:
desiccated
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

100

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

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
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.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000471323
0000204001
0000204003
030M4627V
0000204001

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

K C Murdock et al.
Journal of medicinal chemistry, 36(15), 2098-2101 (1993-07-23)
The selective phosphorylation of bisantrene (1) affords bis(phosphonoguanidinic acid) 6, a prodrug with enhanced aqueous solubility (as sodium salt 7) at physiological pH. Unlike 1, in a rat tail vein model, no precipitation was observed when bis(phosphonoguanidinic acid) 6 was
S Venitt et al.
Journal of medicinal chemistry, 41(19), 3748-3752 (1998-09-11)
Fifteen anthracene-9,10-dione ("anthraquinone") derivatives with (omega-aminoalkyl)carboxamido substituents at the 1-, 2-, 1,4-, or 2, 6-ring positions were tested for bacterial mutagenicity in reverse-mutation assays using Salmonella typhimurium frameshift strains TA1538, TA98, and TA97a, in the presence and absence of a
Disposition of bisantrene in humans and rabbits: evidence for intravascular deposition of drug as a cause of phlebitis
Powis G and Kovach JS
Cancer Research, 43(2), 925-929 (1983)
V I Salianov et al.
Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic], 35(1), 19-22 (1990-01-01)
The effect of anthrachinone and anthracene derivatives on linear and circular superstranded molecules of DNA in conditions of their condensation was studied. It was shown that the compounds formed strong intercalation complexes with the molecules of the linear and circular
C Sissi et al.
Molecular pharmacology, 54(6), 1036-1045 (1998-12-18)
To elucidate structure-activity relationships for drugs that are able to poison or inhibit topoisomerase II, we investigated the thermodynamics and stereochemistry of the DNA binding of a number of anthracene derivatives bearing one or two 4, 5-dihydro-1H-imidazol-2-yl-hydrazone side chains (characteristic
View All Related Papers

Global Trade Item Number

SKUGTIN
B4563-50MG04061833228517
B4563-10MG04061833228500

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service