Page last updated: 2024-12-06

bisantrene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Bisantrene is a synthetic anthracenedione anticancer agent that was originally developed for the treatment of acute leukemia. It acts by inhibiting DNA topoisomerase II, an enzyme essential for DNA replication and repair. Bisantrene was shown to be active against leukemia cells in vitro and in vivo, but its clinical development was halted due to its significant toxicity, including cardiotoxicity and bone marrow suppression. However, bisantrene has continued to be studied as a potential therapeutic agent for other cancers, including melanoma, breast cancer, and lung cancer. Its unique mechanism of action and its ability to overcome drug resistance make it a promising candidate for further investigation.'

bisantrene: RN given refers to parent cpd; synonyms CL 216942 & NSC 337766 refers to di-HCl [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bisantrene : A hydrazone resulting from the formal condensation of both of the aldehyde groups of anthracene-9,10-dicarbaldehyde with 2-hydrazinyl-4,5-dihydro-1H-imidazole. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID51323
CHEBI ID88337
SCHEMBL ID7207049
MeSH IDM0098690
PubMed CID5351322
CHEMBL ID25336
SCHEMBL ID8906393
MeSH IDM0098690

Synonyms (55)

Synonym
9,10-anthracendicarbaldehyde bis(2-imidazolin-2-ylhydrazon)
c22h22n8
bisantrene
bisantrenum
bisantreno
NCI60_002970
NCIMECH_000535
NEURO_000174
n-[[10-[(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine
78186-34-2
FT-0630857
SCHEMBL7207049
9,10-anthracendicarbaldehyde bis(2-imidazolin-2-ylhydrazone)
2,2'-[anthracene-9,10-diylbis(methylylidenehydrazine-2,1-diylidene)]diimidazolidine
CHEBI:88337
9,10-bis((e)-(2-(4,5-dihydro-1h-imidazol-2-yl)hydrazono)methyl)anthracene
Q27160191
cl216942
DTXSID50868470
9,10-anthracenedicarboxaldehyde, bis((4,5-dihydro-1h-imidazol-2-yl)hydrazone)
bisantrenum [inn-latin]
brn 0966309
bisantreno [inn-spanish]
bisantrene [inn]
unii-39c34m111k
39c34m111k ,
9,10-anthracenedicarboxaldehyde, bis(4,5-dihydro-1h-imidazol-2-ylhydrazone),dihydrochloride
9,10-anthracenedicarbaldehyde bis(4,5-dihydro-1h-imidazol-2-ylhydrazone)
n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazono)methyl]-9-anthryl]methyleneamino]-4,5-dihydro-1h-imidazol-2-amine
nsc-337766
cl 216942
CHEMBL25336 ,
n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine
x n-4,5-dihydro-1h-2-imidazolamine-10-iminomethyl-9-anthrylmethanimine-4,5-dihydro-1h-2-imidazolamine (bisantrene)
n-anthracen-9-yl methylene n''-[(bis)4,5-dihydro-1h-imidazole-2-yl)-hydrazine
9,10-anthracenedicarboxaldehyde bis(2-imidazolin-2-yl-hydrazone)
bdbm50060768
anthracene-9,10 bis-carbaldehyde 4,5-dihydro-1h-imidazol-2-ylhydrazone
10-imino(4,5-dihydro-1h-2-imidazolamine)methyl-9-anthrylmethan-(4,5-dihydro-1h-2-imidazolamine)imine
9,10-anthracenedicarboxaldehyde bis[(4,5-dihydro-1h-imidazol-2yl)hydrazone)
n-anthracen-bis-9,10-ylmethylene-n''-(4,5-dihydro-1h-imidazol-2-yl)-hydrazine(bisantrene)
AKOS016014320
CCG-35603
bisantrene [mi]
9,10-anthracenedicarboxaldehyde bis(2-imidazolin-2-ylhydrazone)
bisantrene [who-dd]
SCHEMBL8906393
9,10-bis((2-(4,5-dihydro-1h-imidazol-2-yl)hydrazono)methyl)anthracene
HY-100875
CS-6132
9,10-bis(2-(4,5-dihydro-1h-imidazol-2-yl)hydrazono)methyl)anthracene
EX-A2382
BRD-K64298650-300-01-5
AS-75775
AC-35847

Research Excerpts

Overview

Bisantrene (NSC 337766) is an anthracenedicarboxaldehyde hydrazone demonstrating a wide spectrum of activity in animal tumor model systems with no evidence of cardiotoxicity or alopecia, in contrast to doxorubicin. Bisantrene is an effective and well-tolerated agent for the treatment of malignant lymphoma.

ExcerptReferenceRelevance
"Bisantrene (NSC 337766) is an anthracenedicarboxaldehyde hydrazone demonstrating a wide spectrum of activity in animal tumor model systems with no evidence of cardiotoxicity or alopecia, in contrast to doxorubicin. "( Bisantrene (NSC 337766) (CL 216,942) in advanced breast cancer. A cancer and leukemia group B study.
Forastiere, AA; Hughes, AK; Perry, MC; Wood, WC, 1984
)
3.15
"Bisantrene is a substituted anthracene derivative which preclinically demonstrated a spectrum of activity similar to that of doxorubicin but without associated cardiotoxicity. "( Phase I clinical trial of 9,10-anthracene dicarboxaldehyde (Bisantrene) administered in a five-day schedule.
Blum, RH; Hoffman, KS; Levin, M; Muggia, FM; Pinto, CA; Speyer, JL; Spiegel, RJ; Wernz, JC, 1982
)
1.95
"Bisantrene is an anthracene derivative which has demonstrated activity in acute myeloblastic leukemia (AML) and in lymphoma. "( Treatment of relapsed or refractory acute leukemia in childhood with bisantrene combined with high dose aracytine.
Baruchel, A; Deméocq, F; Guillot, T; Leblanc, T; Lemerle, S; Leverger, G; Nelken, B; Schaison, G; Vannier, JP, 1994
)
1.97
"Bisantrene is a well known anticancer drug and has been used clinically for years."( 1D and 2D 1H NMR studies on bisantrene complexes with short DNA oligomers.
Wilson, WD; Yao, S, 1995
)
1.31
"Bisantrene is an effective and well-tolerated agent for the treatment of malignant lymphoma."( Activity of bisantrene in refractory lymphoma.
Cabanillas, F; Hagemeister, FB; McLaughlin, P; Velasquez, WS, 1987
)
1.37
"Bisantrene is an effective drug for metastatic breast cancer that has incomplete cross resistance to doxorubicin, and there was no schedule dependency in this study."( A comparative study of bisantrene given by two dose schedules in patients with metastatic breast cancer.
Blumenschein, GR; Buzdar, AU; Esparza, L; Holmes, FA; Hortobagyi, GN; Yap, HY, 1986
)
1.3
"Bisantrene is a newer anthracycline derivative currently being investigated in phase 2 trials. "( Depression of cardiac function by bisantrene.
Artman, M; Olson, RD; Parrish, MD; Roloff, JS, 1985
)
1.99

Effects

ExcerptReferenceRelevance
"Bisantrene has limited activity in heavily pretreated patients with HD or unfavorable histology in NHL."( A phase II study of bisantrene in malignant lymphomas. A Southwest Oncology Group Study.
Cowan, JD; Jones, SE; Miller, TP; Neilan, BA, 1986
)
1.32

Treatment

ExcerptReferenceRelevance
"Pre-treatment with Bisantrene prior to radiation resulted in an additive effect, similar to that reported with Adriamycin."( Interaction between bisantrene and radiation.
Hernandez, E; Rosenshein, NB, 1985
)
0.91

Toxicity

ExcerptReferenceRelevance
"In this work, we demonstrate a protective effect conferred by the human multidrug resistance gene (MDR1) to populations of the murine hematopoietic system against the toxic effects of bisantrene, a novel intercalating cytotoxic agent under investigation as an anticancer agent."( Retroviral transfer of the human MDR1 gene confers resistance to bisantrene-specific hematotoxicity.
Aksentijevich, I; Cardarelli, CO; Gottesman, MM; Pastan, I, 1996
)
0.72

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic analyses are reported for four patients."( A phase I and pharmacokinetic comparison of hepatic arterial and peripheral vein infusions of bisantrene for liver cancer.
Hersh, M; Kisner, DL; Kuhn, JG; Ludden, TM; Pirtle, TE; von Hoff, DD; Weiss, GR, 1985
)
0.49
" Mass spectrometry confirmation of each drug from patient sample separations is presented to provide unambiguous identification for valid pharmacokinetic parameter determination."( HPLC, MS, and pharmacokinetics of melphalan, bisantrene and 13-cis retinoic acid.
Alberts, DS; Davis, TP; Goodman, GE; Peng, YM, 1982
)
0.52

Compound-Compound Interactions

ExcerptReferenceRelevance
" We demonstrated the synergism of [Bis + ABT199/venetoclax] in combination with panobinostat (Pano), decitabine (DAC), or olaparib (Ola), known inhibitors of BCL2, histone deacetylase, DNA methyltransferase, and poly(ADP-ribose) polymerase, respectively, in AML cells."( Enhanced cytotoxicity of bisantrene when combined with venetoclax, panobinostat, decitabine and olaparib in acute myeloid leukemia cells.
Andersson, BS; Murray, D; Nieto, Y; Popat, U; Valdez, BC; Yuan, B, 2022
)
1.02

Bioavailability

ExcerptReferenceRelevance
" This finding supports our previous recommendation that in clinical trials Bisantrene should be administered at low concentrations over prolonged periods of time to maximize the bioavailability of the drug by minimizing precipitation of the drug in plasma."( Blood and tissue concentrations of Bisantrene measured by a simple fluorometric assay.
Buck, M; Kovach, JS, 1985
)
0.78

Dosage Studied

Bisantrene was administered by 72-h continuous infusion at a dosage level of 240 mg/m2 to 17 patients with metastatic breast cancer who had received only one prior chemotherapy regimen. The initial bisantrene dosing schedule was 260 mg/ m2 every three weeks for good risk patients.

ExcerptRelevanceReference
" The initial bisantrene dosing schedule was 260 mg/m2 every three weeks for good risk patients."( Phase II evaluation of bisantrene hydrochloride in refractory malignant melanoma. A Southwest Oncology Group Study.
Alberts, DS; Cowan, JD; Epstein, RB; Fletcher, WS; Green, SJ; Guy, JT; Mason-Liddil, N; Neilan, B, 1987
)
0.95
" Dosage escalations ranged from 10 to 120 mg/m2 daily for 5 consecutive days."( Phase I clinical and pharmacokinetic study of bisantrene in refractory pediatric solid tumors.
Avery, L; Choi, K; Crom, DB; Douglass, EC; Etcubanas, E; Pratt, CB; Sinkule, JA, 1986
)
0.53
"Bisantrene was administered by 72-h continuous infusion at a dosage level of 240 mg/m2 to 17 patients with metastatic breast cancer who had received only one prior chemotherapy regimen and no prior doxorubicin."( Evaluation of bisantrene administered by 72-hour infusion in women with metastatic breast cancer.
Chang, MN; Ingle, JN; Long, HJ; Schutt, AJ, 1986
)
2.07
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
hydrazoneCompounds having the structure R2C=NNR2, formally derived from aldehydes or ketones by replacing =O by =NNH2 (or substituted analogues).
imidazolidines
anthracenesCompounds containing an anthracene skeleton.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
NADHomo sapiens (human)IC50 (µMol)25.00000.00260.80763.4000AID277029
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (37)

Processvia Protein(s)Taxonomy
protein polyubiquitinationNADHomo sapiens (human)
response to ischemiaNADHomo sapiens (human)
NADH oxidationNADHomo sapiens (human)
ubiquinone metabolic processNADHomo sapiens (human)
xenobiotic metabolic processNADHomo sapiens (human)
nitric oxide biosynthetic processNADHomo sapiens (human)
response to oxidative stressNADHomo sapiens (human)
synaptic transmission, cholinergicNADHomo sapiens (human)
response to nutrientNADHomo sapiens (human)
response to toxic substanceNADHomo sapiens (human)
response to hormoneNADHomo sapiens (human)
response to carbohydrateNADHomo sapiens (human)
response to amineNADHomo sapiens (human)
removal of superoxide radicalsNADHomo sapiens (human)
protein catabolic processNADHomo sapiens (human)
response to estradiolNADHomo sapiens (human)
response to lipopolysaccharideNADHomo sapiens (human)
response to testosteroneNADHomo sapiens (human)
cellular response to oxidative stressNADHomo sapiens (human)
negative regulation of protein catabolic processNADHomo sapiens (human)
vitamin E metabolic processNADHomo sapiens (human)
vitamin K metabolic processNADHomo sapiens (human)
negative regulation of apoptotic processNADHomo sapiens (human)
response to alkaloidNADHomo sapiens (human)
positive regulation of neuron apoptotic processNADHomo sapiens (human)
innate immune responseNADHomo sapiens (human)
cell redox homeostasisNADHomo sapiens (human)
response to ethanolNADHomo sapiens (human)
response to electrical stimulusNADHomo sapiens (human)
cellular response to hydrogen peroxideNADHomo sapiens (human)
NADPH oxidationNADHomo sapiens (human)
cellular response to metal ionNADHomo sapiens (human)
negative regulation of ferroptosisNADHomo sapiens (human)
response to tetrachloromethaneNADHomo sapiens (human)
response to L-glutamineNADHomo sapiens (human)
response to hydrogen sulfideNADHomo sapiens (human)
response to flavonoidNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
RNA bindingNADHomo sapiens (human)
cytochrome-b5 reductase activity, acting on NAD(P)HNADHomo sapiens (human)
superoxide dismutase activityNADHomo sapiens (human)
protein bindingNADHomo sapiens (human)
NADPH dehydrogenase (quinone) activityNADHomo sapiens (human)
identical protein bindingNADHomo sapiens (human)
NADH:ubiquinone reductase (non-electrogenic) activityNADHomo sapiens (human)
NAD(P)H dehydrogenase (quinone) activityNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusNADHomo sapiens (human)
cytoplasmNADHomo sapiens (human)
cytosolNADHomo sapiens (human)
dendriteNADHomo sapiens (human)
neuronal cell bodyNADHomo sapiens (human)
synapseNADHomo sapiens (human)
cytosolNADHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (94)

Assay IDTitleYearJournalArticle
AID117314Percent increase in median life span of BDF1 mice with advanced P-388 leukemia at dose 12.5 mg/kg administered intraperitoneally; 4, 8, 12 days of ip treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID112614Antitumor activity against B-16 melanoma in BDF1 mice expressed as percentage increase in life span at optimum dose of 6 mg/kg1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
N-phosphoryl derivatives of bisantrene. Antitumor prodrugs with enhanced solubility and reduced potential for toxicity.
AID117148Percent increase in median life span of BDF1 mice with Colon 26 at dose 6.2 mg/kg administered intraperitoneally; Range is 114-150%; 1, 5, 9 days of ip treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID8254Effect on DNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 10 ug/mL (*: >1 log cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID211311Percent of DNA remaining uncut after incubation with Topoisomerase II at 1 uM concentration1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues.
AID681572TP_TRANSPORTER: drug resistance in BCRP-expressing MEF3.8 cells2003Cancer research, Mar-15, Volume: 63, Issue:6
Mouse breast cancer resistance protein (Bcrp1/Abcg2) mediates etoposide resistance and transport, but etoposide oral availability is limited primarily by P-glycoprotein.
AID110621Cures is the number of survivors of the total treated mice (10) with P-388 leukemia, at 30 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID201221Bacterial mutagenicity was measured against Salmonella Typhimurium TA1538 at dose range of 0-200 ug/plate1998Journal of medicinal chemistry, Sep-10, Volume: 41, Issue:19
Anthracene-9,10-diones as potential anticancer agents: bacterial mutation studies of amido-substituted derivatives reveal an unexpected lack of mutagenicity.
AID54963Cubic spline relative binding strength was determined by using spectrophotometric titration1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
DNA binding by antitumor anthracene derivatives.
AID8415Effect on protein synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 0.01 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID540068Inhibition of human recombinant NQO1 at 100 uM2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2).
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID55006delta Tm value is the difference between Tm(melting temperature) for calf thymus DNA with drug and without drug(Tm = 71 degree C for DNA alone)1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
DNA binding by antitumor anthracene derivatives.
AID110622Cures is the number of survivors of the total treated mice (10) with advanced B-16 melanoma, at 30 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID95083Effect on RNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 10 ug/mL (*: >1 log cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID88859Antitumor potency against human ovarian cancer cells in clonogenic assay1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
DNA binding by antitumor anthracene derivatives.
AID110630Cures is the number of survivors of the total treated mice (42) with P-388 leukemia, at 30 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID95078Effect on DNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 1 ug/mL. (*: >50% cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID110626Cures is the number of survivors of the total treated mice (20) with B-16 melanoma, at 60 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID117138Percent increase in median life span of BDF1 mice with B-16 melanoma at dose 6 mg/kg administered intraperitoneally; range 98-122%; 1-9 days of ip treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID112757Antitumor activity against P388 leukemia in BDF1/CDF1 mice expressed as percentage increase in life span at optimum dose of 12.5 mg/kg1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
N-phosphoryl derivatives of bisantrene. Antitumor prodrugs with enhanced solubility and reduced potential for toxicity.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID277029Inhibition of human recombinant NQO12006Bioorganic & medicinal chemistry letters, Dec-15, Volume: 16, Issue:24
In silico identification and biochemical characterization of novel inhibitors of NQO1.
AID8248Effect on DNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 0.01 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID8412Effect on RNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 10 ug/mL (*: >1 log cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID26641pKa value for amino group in the compound1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
DNA binding by antitumor anthracene derivatives.
AID117316Percent increase in median life span of BDF1 mice with madison lung 109 leukemia administered intraperitoneally1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID110634Cures is the number of survivors of the total treated mice (6) with P-388 leukemia, at 30 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID95081Effect on RNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 0.01 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID95075Effect on DNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 0.1 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID143570Compound was tested for potency against human myeloma 8226 cells (40 fold resistant to doxorubicin).1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID8423In vitro inhibition of human 8226 myeloma tumor cell line growth.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID201225Bacterial mutagenicity was measured against Salmonella Typhimurium TA98 at dose range of 0-20 ug/plate1998Journal of medicinal chemistry, Sep-10, Volume: 41, Issue:19
Anthracene-9,10-diones as potential anticancer agents: bacterial mutation studies of amido-substituted derivatives reveal an unexpected lack of mutagenicity.
AID211310Percent of DNA remaining uncut after incubation with Topoisomerase II at 0.1 uM concentration1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues.
AID95225Effect on protein synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 1 ug/mL. (*: >50% cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID8407Effect on RNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 0.01 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID110624Cures is the number of survivors of the total treated mice (17) with L-1210 leukemia, at 30 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID214777In vitro inhibition of human UACC-66 ovarian tumor cell line growth.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID201679Compound was tested for potency against human colon carcinoma SW 480 cells in a sulforhodamine B assay.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID117305Percent increase in median life span of BDF1 mice with advanced B-16 melanoma at dose 12.5 mg/kg administered intraperitoneally; 5, 9, 13 days of ip treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID8408Effect on RNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 0.1 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID117157Percent increase in median life span of BDF1 mice with P-388 leukemia at dose 12.5 mg/kg administered intraperitoneally; 1, 5, 9 days of ip treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID82014Tested in vitro for inhibitory activity of human tumor cell growth against HEC 1A endometrial tumor, by using clonogenic assays.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID110627Cures is the number of survivors of the total treated mice (20) with Colon 26, at 60 days.1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID143571Compound was tested for potency against human myeloma 8226 cells using MTT assay method.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID8249Effect on DNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 0.1 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID8416Effect on protein synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 0.1 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID8413Effect on RNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 1 ug/mL. (*: >50% cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID110639Cures is the number of survivors of the total treated mice (6) with advanced L-1210 leukemia; treatment day +2 iv1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID26757DNA binding dissociation constant as KD; No data1984Journal of medicinal chemistry, Apr, Volume: 27, Issue:4
Interactions of antitumor drugs with natural DNA: 1H NMR study of binding mode and kinetics.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID95082Effect on RNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 0.1 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID95224Effect on protein synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 10 ug/mL (*: >1 log cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID122575Number of survivors after treating 12 mice (infected with B16 melanoma) for 60 days1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
N-phosphoryl derivatives of bisantrene. Antitumor prodrugs with enhanced solubility and reduced potential for toxicity.
AID216581Compound was tested for potency against human colon carcinoma WiDr cells in a sulforhodamine B assay.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID54620Apparent binding constant (McGhee-von Hippel) was determined by using spectrophotometric titration1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
DNA binding by antitumor anthracene derivatives.
AID110799Number of survivors after treating 42 mice (infected with P388 leukemia) for 30 days1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
N-phosphoryl derivatives of bisantrene. Antitumor prodrugs with enhanced solubility and reduced potential for toxicity.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID8493Compound was tested for potency against human lung A549 cells using sulforhodamine B assay.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID8421Effect on protein synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 1 ug/mL. (*: >50% cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID95074Effect on DNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 0.01 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID117308Percent increase in median life span of BDF1 mice with advanced L-1210 leukemia1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID95217Effect on RNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 1 ug/mL. (*: >50% cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID123620Percent tumor inhibition at non-lethal dose was determined in BDF1 mice with madison lung 109 leukemia; 1, 5, 9 days of sc treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID98398Compound was tested for potency against multidrug-resistant murine leukemia L1210 cells1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID8420Effect on protein synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 10 ug/mL (*: >1 log cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID9989Cell cytotoxicity was determined against human ovarian cancer (A2780) cell line1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues.
AID680880TP_TRANSPORTER: efflux in S1-B1-20 cells1994Oncology research, , Volume: 6, Issue:7
P-glycoprotein mediates profound resistance to bisantrene.
AID8255Effect on DNA synthesis was determined by incorporation of radioligand into 8226 human myeloma cells at a concentration of 1 ug/mL. (*: >50% cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID98397Compound was tested for potency against multi drug resistant murine leukemia L1210 cells.1997Journal of medicinal chemistry, Nov-07, Volume: 40, Issue:23
1,4-disubstituted anthracene antitumor agents.
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID95222Effect on protein synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 0.1 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID211312Percent of DNA remaining uncut after incubation with Topoisomerase II at 10 uM concentration1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues.
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID216123Tested in vitro for inhibitory activity of human tumor cell growth against WIDR colon tumor, by using clonogenic assays.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID95221Effect on protein synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 0.01 ug/mL1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID540069Inhibition of human recombinant NQO2 at 100 uM2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2).
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID201223Bacterial mutagenicity was measured against Salmonella Typhimurium TA97a at dose range of 0-400 ug/plate1998Journal of medicinal chemistry, Sep-10, Volume: 41, Issue:19
Anthracene-9,10-diones as potential anticancer agents: bacterial mutation studies of amido-substituted derivatives reveal an unexpected lack of mutagenicity.
AID95077Effect on DNA synthesis was determined by incorporation of radioligand into L1210 murine leukemia at a concentration of 10 ug/mL (*: >1 log cell kill)1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
New antitumor agents containing the anthracene nucleus.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID82834Cell cytotoxicity was determined against human promyelocytic leukemia (HL60) cell line1998Bioorganic & medicinal chemistry letters, Jan-20, Volume: 8, Issue:2
Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues.
AID117149Percent increase in median life span of BDF1 mice with L-1210 leukemia at dose 12.5 mg/kg administered intraperitoneally; 1, 5, 9 days of ip treatment relative to tumor inoculation1982Journal of medicinal chemistry, May, Volume: 25, Issue:5
Antitumor agents. 2. Bisguanylhydrazones of anthracene-9,10-dicarboxaldehydes.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (121)

TimeframeStudies, This Drug (%)All Drugs %
pre-199091 (75.21)18.7374
1990's19 (15.70)18.2507
2000's3 (2.48)29.6817
2010's5 (4.13)24.3611
2020's3 (2.48)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.87

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.87 (24.57)
Research Supply Index4.86 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index48.16 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.87)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials9 (7.56%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies2 (1.68%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other108 (90.76%)84.16%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (3)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
An Open-label, Phase II, Two-stage, Study of Bisantrene(Xantrene) in Combination With Fludarabine and Clofarabine as Salvage Therapy for Adult Patients With Relapsed or Refractory Acute Myeloid Leukemia (AML) [NCT04989335]Phase 229 participants (Anticipated)Interventional2021-08-02Recruiting
An Open-label Two Strata Study of Bisantrene in Combination With Cytarabine Arabinoside or Bisantrene in Combination With Oral Decitabine/Cedazuridine for the Treatment of Acute Myeloid Leukemia Patients With Extramedullary Disease [NCT05456269]Phase 10 participants (Actual)Interventional2022-07-29Withdrawn(stopped due to commercial reason)
Bisantrene for Relapsed /Refractory Acute Myelogenous Leukemia (AML) [NCT03820908]Phase 210 participants (Actual)Interventional2019-07-18Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]