Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C22H27N5O4.4ClH.H2O |
Molecular Weight | 1014.821 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.Cl.Cl.Cl.OCCNCCNC1=CC=C2N(CCNCCO)N=C3C2=C1C(=O)C4=C3C=CC=C4O.OCCNCCNC5=CC=C6N(CCNCCO)N=C7C6=C5C(=O)C8=C7C=CC=C8O
InChI
InChIKey=CNQCTSLNJJVSAU-UHFFFAOYSA-N
InChI=1S/2C22H27N5O4.4ClH.H2O/c2*28-12-9-23-6-7-25-15-4-5-16-20-19(15)22(31)18-14(2-1-3-17(18)30)21(20)26-27(16)11-8-24-10-13-29;;;;;/h2*1-5,23-25,28-30H,6-13H2;4*1H;1H2
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
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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A novel 9-aza-anthrapyrazole effective against human prostatic carcinoma xenografts. | 2001 |
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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 |
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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 |
|
Structure-activity studies with cytotoxic anthrapyrazoles. | 2006 Jun |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:59:49 GMT 2023
by
admin
on
Fri Dec 15 15:59:49 GMT 2023
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Record UNII |
W6E275IURX
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Validated (UNII)
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C2107
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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |