Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H27N5O4 |
| Molecular Weight | 425.4809 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCNCCNC1=CC=C2N(CCNCCO)N=C3C2=C1C(=O)C4=C3C=CC=C4O
InChI
InChIKey=YROQEQPFUCPDCP-UHFFFAOYSA-N
InChI=1S/C22H27N5O4/c28-12-9-23-6-7-25-15-4-5-16-20-19(15)22(31)18-14(2-1-3-17(18)30)21(20)26-27(16)11-8-24-10-13-29/h1-5,23-25,28-30H,6-13H2
Losoxantrone is an anthrapyrazole that induces both single and double strand breaks in DNA and is a potent inhibitor of DNA synthesis. The drug is in clinical trials for the treatment of breast cancer and of prostate cancer that is refractory to androgen ablation. Acute toxicity is negligible. Losoxantrone may be less cardiotoxic than doxorubicin. Up to 40% of patients encounter alopecia. 3% of patients develop congestive heart failure. Losoxantrone had been in phase II clinical trial for the treatment of breast and prostate cancer. However, this development was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Separation methods for anthraquinone related anti-cancer drugs. | 2001 Nov 25 |
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| The oxidative biotransformation of losoxantrone (CI-941). | 2002 Apr |
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| Phase I study of the combination of losoxantrone and cyclophosphamide in patients with refractory solid tumours. | 2002 Feb 12 |
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| A structure-based 3D-QSAR study of anthrapyrazole analogues of the anticancer agents losoxantrone and piroxantrone. | 2006 Jul-Aug |
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| Structure-activity studies with cytotoxic anthrapyrazoles. | 2006 Jun |
Patents
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NCI_THESAURUS |
C2107
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DTXSID60236949
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Losoxantrone
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100000082057
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47KPH00809
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88303-60-0
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C1521
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C050637
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72116
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6989
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SUB08597MIG
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CHEMBL83520
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
