Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H20N4O6 |
Molecular Weight | 364.3532 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)NC1=C(N2CC2)C(=O)C(NC(=O)OCC)=C(N3CC3)C1=O
InChI
InChIKey=WVYXNIXAMZOZFK-UHFFFAOYSA-N
InChI=1S/C16H20N4O6/c1-3-25-15(23)17-9-11(19-5-6-19)14(22)10(18-16(24)26-4-2)12(13(9)21)20-7-8-20/h3-8H2,1-2H3,(H,17,23)(H,18,24)
Molecular Formula | C16H20N4O6 |
Molecular Weight | 364.3532 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Diaziquone is an aziridinylbenzoquinone with properties suggestive of an alkylating agent. The drug has shown broad antitumor activity against numerous transplantable murine tumors including curative activity against several intracerebrally implanted tumors. Diaziquone is rapidly and extensively metabolized by the liver. Diaziquone is a potent marrow suppressive agent inducing significant degrees of leukopenia, granulocytopenia, and thrombocytopenia in humans. Thrombocytopenia is often severe. Diaziquone alkylates and cross-links DNA during all phases of the cell cycle, resulting in disruption of DNA function, cell cycle arrest, and apoptosis. This agent can also form free radicals, thereby initiating DNA damage via DNA strand breaks. Due to its lipophilicity, diaziquone readily crosses the blood brain barrier. In phase I and preliminary phase II trials, diaziquone has demonstrated activity against primary brain tumors. Little activity has been seen in other tumor categories.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells. | 1996 Dec 13 |
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BCL-2 is involved in preventing oxidant-induced cell death and in decreasing oxygen radical production. | 2001 |
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Anticancer drug-induced kidney disorders. | 2001 Jan |
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Medulloblastoma/primitive neuroectodermal tumour studied as a Matrigel enhanced subcutaneous xenograft model. | 2001 Mar |
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Response of short-term cultures derived from human malignant glioma to aziridinylbenzoquinone, etoposide and doxorubicin: an in vitro phase II trial. | 2001 Oct |
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Prognostic factors and outcome of core binding factor acute myeloid leukemia patients with t(8;21) differ from those of patients with inv(16): a Cancer and Leukemia Group B study. | 2005 Aug 20 |
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Complete remissions in chemotherapy of lung cancer models induced in mice by asbestos. | 2005 Jan |
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Outcome of induction and postremission therapy in younger adults with acute myeloid leukemia with normal karyotype: a cancer and leukemia group B study. | 2005 Jan 20 |
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Cytotoxic and antiangiogenic activity of AW464 (NSC 706704), a novel thioredoxin inhibitor: an in vitro study. | 2005 Jan 31 |
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Sequential multiagent chemotherapy is not superior to high-dose cytarabine alone as postremission intensification therapy for acute myeloid leukemia in adults under 60 years of age: Cancer and Leukemia Group B Study 9222. | 2005 May 1 |
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Sonochemically induced covalent binding of calf thymus DNA by aziridinylquinones. | 2005 Oct |
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Phase II trial of docetaxel in advanced or metastatic endometrial cancer: a Japanese Cooperative Study. | 2005 Oct 31 |
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The lethal effect of bis-type azridinylnaphthoquinone derivative on oral cancer cells (OEC-M1) associated with anti-apoptotic protein bcl-2. | 2006 Jan 1 |
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Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006 Jul 26 |
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A novel screen using the Reck tumor suppressor gene promoter detects both conventional and metastasis-suppressing anticancer drugs. | 2010 Aug |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:14:32 GMT 2023
by
admin
on
Fri Dec 15 15:14:32 GMT 2023
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Record UNII |
FQL5EUP13W
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
383
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NCI_THESAURUS |
C292
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CHEMBL36016
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57998-68-2
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FQL5EUP13W
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DTXSID40206721
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182986
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C1363
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5124
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C029108
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SUB07070MIG
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m4269
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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ACTIVE MOIETY |