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
Molecular Formula | C22H27N5O4 |
Molecular Weight | 425.4809 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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Monotherapy of metastatic breast cancer: a review of newer agents. | 1999 |
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The displacement of iron(III) from its complexes with the anticancer drugs piroxantrone and losoxantrone by the hydrolyzed form of the cardioprotective agent dexrazoxane. | 1999 Nov-Dec |
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A multicenter phase II trial of losoxantrone (DuP-941) in hormone-refractory metastatic prostate cancer. | 2000 Apr |
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Elimination pathways of [14C]losoxantrone in four cancer patients. | 2001 Feb |
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DNA-interactive anticancer aza-anthrapyrazoles: biophysical and biochemical studies relevant to the mechanism of action. | 2001 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:17:39 UTC 2023
by
admin
on
Sat Dec 16 16:17:39 UTC 2023
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Record UNII |
47KPH00809
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C2107
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DTXSID60236949
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Losoxantrone
Created by
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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
Created by
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |