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 |
|---|---|---|
| A novel screen using the Reck tumor suppressor gene promoter detects both conventional and metastasis-suppressing anticancer drugs. | 2010-08 |
|
| Cytotoxic activities of several geranyl-substituted flavanones. | 2010-04-23 |
|
| A Model for NAD(P)H:Quinoneoxidoreductase 1 (NQO1) Targeted Individualized Cancer Chemotherapy. | 2009 |
|
| DNA-metallodrugs interactions signaled by electrochemical biosensors: an overview. | 2007 |
|
| Altered expression of thioredoxin reductase-1 in dysplastic bile ducts and cholangiocarcinoma in a hamster model. | 2006-09 |
|
| Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006-07-26 |
|
| The lethal effect of bis-type azridinylnaphthoquinone derivative on oral cancer cells (OEC-M1) associated with anti-apoptotic protein bcl-2. | 2006-01-01 |
|
| Phase II trial of docetaxel in advanced or metastatic endometrial cancer: a Japanese Cooperative Study. | 2005-10-31 |
|
| Sonochemically induced covalent binding of calf thymus DNA by aziridinylquinones. | 2005-10 |
|
| 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. | 2005-08-20 |
|
| 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. | 2005-05-01 |
|
| Cytotoxic and antiangiogenic activity of AW464 (NSC 706704), a novel thioredoxin inhibitor: an in vitro study. | 2005-01-31 |
|
| Outcome of induction and postremission therapy in younger adults with acute myeloid leukemia with normal karyotype: a cancer and leukemia group B study. | 2005-01-20 |
|
| Complete remissions in chemotherapy of lung cancer models induced in mice by asbestos. | 2005-01 |
|
| The p53-dependent apoptotic pathway of breast cancer cells (BC-M1) induced by the bis-type bioreductive compound aziridinylnaphthoquinone. | 2005 |
|
| Pharmacokinetics following intraventricular administration of chemotherapy in patients with neoplastic meningitis. | 2005 |
|
| Sonochemistry of antitumor quinones in argon-saturated aqueous solutions: enhanced ferricytochrome c reduction. | 2004-07 |
|
| Gateways to Clinical Trials. | 2002-04 |
|
| Response of short-term cultures derived from human malignant glioma to aziridinylbenzoquinone, etoposide and doxorubicin: an in vitro phase II trial. | 2001-10 |
|
| Medulloblastoma/primitive neuroectodermal tumour studied as a Matrigel enhanced subcutaneous xenograft model. | 2001-03 |
|
| Detecting treatment-by-centre interaction in multi-centre clinical trials. | 2001-01-30 |
|
| Anticancer drug-induced kidney disorders. | 2001-01 |
|
| BCL-2 is involved in preventing oxidant-induced cell death and in decreasing oxygen radical production. | 2001 |
|
| The role of NAD(P)H:quinone oxidoreductase in quinone-mediated p21 induction in human colon carcinoma cells. | 1997-10-15 |
|
| Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells. | 1996-12-13 |
|
| Activation and deactivation of quinones catalyzed by DT-diaphorase. Evidence for bioreductive activation of diaziquone (AZQ) in human tumor cells and detoxification of benzene metabolites in bone marrow stroma. | 1990 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:51:23 GMT 2025
by
admin
on
Mon Mar 31 17:51:23 GMT 2025
|
| Record UNII |
FQL5EUP13W
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
FDA ORPHAN DRUG |
383
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
||
|
NCI_THESAURUS |
C292
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
CHEMBL36016
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
57998-68-2
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
FQL5EUP13W
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
853
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
100000082906
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
42616
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
DTXSID40206721
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
90185
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
182986
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
C1363
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
5124
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
C029108
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
SUB07070MIG
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | |||
|
m4269
Created by
admin on Mon Mar 31 17:51:23 GMT 2025 , Edited by admin on Mon Mar 31 17:51:23 GMT 2025
|
PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
