U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H22N8
Molecular Weight 398.4645
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BISANTRENE

SMILES

c1ccc2c(c1)c(/C(/[H])=N/NC3=NCCN3)c4ccccc4c2/C(/[H])=N/NC5=NCCN5

InChI

InChIKey=NJSMWLQOCQIOPE-OCHFTUDZSA-N
InChI=1S/C22H22N8/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)/b27-13+,28-14+

HIDE SMILES / InChI

Molecular Formula C22H22N8
Molecular Weight 398.4645
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Bisantrene was classed as an anthracycline chemotherapeutic agent. It inhibits replication, kills tumor cells in clonogenic assays, and intercalates with DNA, where it inhibits both DNA and RNA synthesis. Bisantrene preferentially binds to A-T rich regions of DNA, where it effects changes to supercoiling and initiates strand breaks in association with DNA-associated proteins. This results from the inhibition of the enzyme topoisomerase II, which relaxes DNA coiling during replication and transcription. Toxicity studies in dogs and monkeys revealed that leukopenia, anorexia, diarrhea injection site necrosis, enterocolitis, muscle degeneration, and pulmonary edema were observed with high doses. Bisantrene was found to have less associated cardiotoxicity than other anthracenes. The existing data for bisantrene clearly demonstrated activity in acute myeloid leukemia, and in other indications including lymphoma, refractory breast cancer, and ovarian cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.34 µM [IC50]
PubMed

PubMed

TitleDatePubMed
A randomized trial of doxorubicin, mitoxantrone and bisantrene in advanced breast cancer (a South West Oncology Group Study).
1985
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:22:00 UTC 2021
Edited
by admin
on Sat Jun 26 07:22:00 UTC 2021
Record UNII
39C34M111K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BISANTRENE
INN   MI   WHO-DD  
INN  
Official Name English
9,10-ANTHRACENEDICARBOXALDEHYDE BIS(2-IMIDAZOLIN-2-YLHYDRAZONE)
Systematic Name English
BISANTRENE [INN]
Common Name English
BISANTRENE [WHO-DD]
Common Name English
BISANTRENE [MI]
Common Name English
9,10-ANTHRACENEDICARBOXALDEHYDE, BIS((4,5-DIHYDRO-1H-IMIDAZOL-2-YL)HYDRAZONE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C253
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
Code System Code Type Description
MESH
C031404
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
FDA UNII
39C34M111K
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
NCI_THESAURUS
C1019
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
CAS
78186-34-2
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
PUBCHEM
5351322
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
EVMPD
SUB05847MIG
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
MERCK INDEX
M2518
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL139554
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
DRUG CENTRAL
376
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
INN
5131
Created by admin on Sat Jun 26 07:22:00 UTC 2021 , Edited by admin on Sat Jun 26 07:22:00 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY