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B4563

Bisantrene dihydrochloride

≥98% (HPLC)

Synonym(s):

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

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000471323
0000204001
0000204003
030M4627V
0000204001

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S Yao et al.
Science in China. Series B, Chemistry, life sciences & earth sciences, 38(12), 1462-1472 (1995-12-01)
The binding of bisantrene to four DNA tetramers, d(CGCG)2, d(GCGC)2, d(CATG)2, and d(GTAC)2, was investigated by 1D and 2D NMR spectroscopy. Bisantrene is a well known anticancer drug and has been used clinically for years. DNA is believed to be
A Spadea et al.
Leukemia & lymphoma, 9(3), 217-220 (1993-02-01)
Because of the lack of standard treatment in refractory and relapsed acute myelogenous leukemia (AML) several new drugs have been employed alone to evaluate their efficacy in this peculiar category of patient. Bisantrene, a new anthracene bishydrazone derivative, has shown
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)
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

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