bisantrene bisantrene bisantrene, trademarked as zantrène, is an anthracenyl bishydrazone with anthracycline-like antineoplastic activity and an antimetabolite. bisantrene intercalates with and disrupts the configuration of dna, resulting in dna single-strand breaks, dna-protein crosslinking, and inhibition of dna replication. this agent is similar to doxorubicin in activity, but unlike anthracyclines like doxorubicin, exhibits little cardiotoxicity. bisantreneidentifiers iupac name n-anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine cas number78186-34-2pubchem cid51323chemspider46491unii39c34m111kkeggd03130chebichebi:88337chemblchembl25336chemical and physical dataformulac22h22n8molar mass398.474 g·mol−13d model (jsmol)interactive image smiles c(=nnc1=nccn1)c1c2ccccc2c(c=nnc2=nccn2)c2ccccc12 inchi 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)key:njsmwlqocqiope-uhfffaoysa-n bisantrene has been identified a potent (ic50 142nm) fat mass and obesity (fto) associated protein a m6a rna demethylase. bisantrene is undergoing phase ii trials to assess its efficacy to target cancers and side effects. medical uses clinical trials of bisantrene in the 1980s showed efficacy in a range of leukaemias (including acute myeloid leukaemia), breast cancer, and ovarian cancer. side effects high doses of bisantrene (above 200 mg/m2/day) cause side effects typical of anthracycline chemotherapeutics. common side effects include hair loss, bone marrow suppression, vomiting, rash, and inflammation of the mouth. for a chemotherapy drug, it is considered to have relatively low toxicity. unlike other anthracycline chemotherapeutics, bisantrene shows low levels of cardiotoxicity. in a phase iii metastatic breast cancer clinical, patients were exposed to cumulative doses in excess of 5440 mg/m2 without developing cardiac damage. the same study observed significantly lower rates of hair loss and nausea compared to patients given doxorubicin. mechanism of action bisantrene contains an appropriately sized planar electron-rich chromophore to be a dna intercalating agent, and in vitro, it is a potent inhibitor of dna and rna synthesis. history bisantrene was developed by lederle laboratories during the 1970s, a subsidiary of american cyanamid, as a less cardiotoxic alternative to anthracyclines. across the 1980s and early 1990s, over 40 clinical trials were conducted using bisantrene. the national cancer institute (nci)] undertook a large scale trial using bisantrene under the name "orange crush", including a range of preclinical trials which found bisantrene to be inactive when taken orally, though was found to be efficacy towards some cancer cells intravenous, intraperitoneal, or subcutaneous. in the 1980s, forty-four patients with metastatic breast cancer who had undergone extensive combination chemotherapy with doxorubicin and had failed to respond to the combination, were treated with bisantrene. from 40 patients that were evaluated, 9 showed a partial response, and 18 showed the cancer was not progressive but stabilised. bisantrene was approved for human medical use in france in 1990 to target acute myeloid leukemia (aml) cancers. it has undergone 46 phase ii trials with 1,800 patients to test its efficacy against fighting cancer cells. the drug was delisted in the early 1990s due to a series of pharmaceutical mergers and acquisitions. society and culture names its chemical name is 9, 10-antrhracenedicarboxaldehydebis dihydrochloride. bisantrene was given the nickname “orange crush” in the 1980s due to its fluorescent orange color when in solution. bisantrene is also referred to as cs1 in cancer research journals.