Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H25N5O4.ClH |
Molecular Weight | 447.915 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCCCNC1=C2C3=C(C=C1)N(CCNCCO)N=C3C4=C(O)C=CC(O)=C4C2=O
InChI
InChIKey=VPNCYQLYSZKURZ-UHFFFAOYSA-N
InChI=1S/C21H25N5O4.ClH/c22-6-1-7-24-12-2-3-13-17-16(12)21(30)19-15(29)5-4-14(28)18(19)20(17)25-26(13)10-8-23-9-11-27;/h2-5,23-24,27-29H,1,6-11,22H2;1H
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 | C21H25N5O4 |
Molecular Weight | 411.4543 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Piroxantrone is one of a series of compounds commonly known as anthrapyrazoles developed in an effort to combine the broad antitumor activity of the anthracyclines with decreased myocardial toxicity. The mechanism of action of piroxantrone and other anthrapyrazoles is incompletely understood but likely involves DNA binding with induction of DNA strand breaks, DNA-protein cross-linking, and inhibition of DNA, RNA, and protein synthesis. Collectively, these findings suggested an interaction with topoisomerase II. Piroxantrone demonstrated antitumor activity in a wide spectrum of experimental systems against breast carcinoma, colon carcinoma, sarcoma, melanoma and leukemia. Piroxantrone is inactive in patients with persistent, progressive, or recurrent ovarian cancer who recently had received a platinum-based regimen. Piroxantrone has detectable but minimal activity against disseminated malignant melanoma. A phase II clinical trial of the piroxantrone administration for the treatment of advanced metastatic or recurrent endometrial cancer was prematurely terminated due to lack of patient accrual.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Phase II trial of piroxantrone for advanced or metastatic soft tissue sarcomas. A Southwest Oncology Group study. | 1993 Nov |
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A phase II trial of piroxantrone in adenocarcinoma of the pancreas. A Southwest Oncology Group study. | 1993 Nov |
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Phase II trial of piroxantrone in metastatic gastric adenocarcinoma. | 1994 |
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Phase II trial of piroxantrone in gastric carcinoma. A Southwest Oncology Group study. | 1994 |
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Conformational drug determinants of the sequence specificity of drug-stimulated topoisomerase II DNA cleavage. | 1994 Jan 28 |
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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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7774846
The piroxantrone starting dose was 120 mg/m2, with the provision to escalate to 150 and 180 mg/m2 every 21 days.
Route of Administration:
Intravenous
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:27:49 GMT 2023
by
admin
on
Sat Dec 16 19:27:49 GMT 2023
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Record UNII |
PWB7VW68W4
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Record Status |
Validated (UNII)
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Record Version |
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118201-50-6
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DTXSID70922629
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PWB7VW68W4
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349174
Created by
admin on Sat Dec 16 19:27:50 GMT 2023 , Edited by admin on Sat Dec 16 19:27:50 GMT 2023
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