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Details

Stereochemistry ACHIRAL
Molecular Formula C12H13N3O2
Molecular Weight 231.2505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIAZIQUONE

SMILES

O=C1C=C(N2CC2)C(=O)C(N3CC3)=C1N4CC4

InChI

InChIKey=PXSOHRWMIRDKMP-UHFFFAOYSA-N
InChI=1S/C12H13N3O2/c16-9-7-8(13-1-2-13)12(17)11(15-5-6-15)10(9)14-3-4-14/h7H,1-6H2

HIDE SMILES / InChI

Molecular Formula C12H13N3O2
Molecular Weight 231.2505
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Triaziquone is a benzoquinone-containing alkylating agent. Triaziquone was shown to have activity in a variety of different animal tumors in vitro and in vivo and in human tumors. This agent presumably produces its antitumor effects by alkylation of cellular components, and has been shown to inhibit DNA and RNA synthesis. This agent is a substrate for both one and two-electron reducing agents and that the cytotoxic activity may result from protein alkylation and oxidative stress. Triaziquone was used clinically in the 1960s for the treatment of a number of cancers . It was used intravenously in the treatment of leukemias and lymphomas like chronic lymphocytic leukemia and Hodgkin's disease, and for ovarian cancer. The agent was also used as an ointment for basal cell skin cancers. Because of its toxicity to bone marrow and blood vessel walls it has been replaced by more effective agents and has not been used clinically for many years.

Originator

Sources: Gauss, W.: Über die umsetzung einiger alkoxy-p-benzochinone mit äthylenimin. Chem Ber 91, 2216-2222 (1958)
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/11056078

Approval Year

PubMed

PubMed

TitleDatePubMed
Synthesis and antitumor evaluation of novel bis-triaziquone derivatives.
2009 Jun 29
Topical immunotherapy in alopecia areata.
2010 Jan
A study on inhibition mechanism of breast cancer cells by bis-type triaziquone.
2010 Jul 10
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:59:55 UTC 2023
Edited
by admin
on Fri Dec 15 18:59:55 UTC 2023
Record UNII
F3D5D9P25I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIAZIQUONE
HSDB   INN   MI   WHO-DD  
INN  
Official Name English
TRIS(1-AZIRIDINYL)-P-BENZOQUINONE
Common Name English
Triaziquone [WHO-DD]
Common Name English
triaziquone [INN]
Common Name English
RIKER 601
Code English
BAYER-3231
Code English
TRIS(AZIRIDINYL)-PARA-BENZOQUINONE
Common Name English
BAYER 3231
Code English
TRIAZIQUONE [MI]
Common Name English
TEIB
Common Name English
TRIS(AZIRIDINYL)-PARA-BENZOQUINONE [IARC]
Common Name English
TRIAZIQUONE [HSDB]
Common Name English
NSC-29215
Code English
TRIETHYLENEIMINOBENZOQUINONE
Common Name English
RIKER-601
Code English
Classification Tree Code System Code
WHO-VATC QL01AC02
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
NCI_THESAURUS C292
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
WHO-ATC L01AC02
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
Code System Code Type Description
WIKIPEDIA
TRIAZIQUONE
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
EVMPD
SUB11257MIG
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
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PUBCHEM
6235
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL313302
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
MESH
D014228
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
INN
1720
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
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EPA CompTox
DTXSID1021370
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
NSC
29215
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
DRUG BANK
DB13304
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-692-6
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
DRUG CENTRAL
4372
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
HSDB
7306
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
SMS_ID
100000077492
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
CAS
68-76-8
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
NCI_THESAURUS
C903
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
FDA UNII
F3D5D9P25I
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
MERCK INDEX
m11034
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY Merck Index
CHEBI
27090
Created by admin on Fri Dec 15 18:59:55 UTC 2023 , Edited by admin on Fri Dec 15 18:59:55 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY