Page last updated: 2024-12-05

triaziquone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Triaziquone: Alkylating antineoplastic agent used mainly for ovarian tumors. It is toxic to skin, gastrointestinal tract, bone marrow and kidneys. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

triaziquone : A member of the class of 1,4-benzoquinones that is 1,4-benzoquinone in which three of the ring hydrogens are replaced by aziridin-1-yl groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6235
CHEMBL ID313302
CHEBI ID27090
SCHEMBL ID8303
MeSH IDM0021909

Synonyms (116)

Synonym
riker-601
bayer-3231
CHEMBL313302
chebi:27090 ,
2,5-cyclohexadiene-1,4-dione, 2,3,5-tris(1-aziridinyl)-
2,5-tris(ethylenimino)-p-benzoquinone
2,5-tris(ethyleneimino)benzoquinone
treninon
2,5-ethylenimine-1,4-benzoquinone
wln: l6v dvj b- at3ntj& c- at3ntj& e- at3ntj
tris(1-aziridinyl)-p-benzoquinone
triaziquon
triethyleneiminobenzoquinone
bay-3231
trenimon
2,5-tris(aziridinyl)-1,4-benzoquinone
triazichon
tris(ethyleneimino)benzoquinone
nsc-29215
teib
2,5-tris(ethylenimino)-1,4-benzoquinone
a 163
oncovedex
2,4-dione, 2,3,5-tris(1-aziridinyl)-
bayer 3231
1,1''-(3,6-dioxo-1,4-cyclohexadiene-1,2,4-triyl)trisaziridine
trisaethyleniminobenzochinon
2,5-triethyleneimino-1,4-benzoquinone
oncoredox
2,5-tris(aziridino)-1,4-benzoquinone
aziridine,1',1''-(3,6-dioxo-1,4-cyclohexadiene-1,2,4-triyl)tris-
p-benzoquinone,3,5-tris(1-aziridinyl)-
68-76-8
tris(aziridinyl)-p-benzoquinone
p-benzoquinone, tris(1-aziridinyl)-
2,5-triethyleneimino-p-benzoquinone
triethyleneaminobenzoquinone
10257 r.p.
nsc29215
prenimon
2,5-tris(1-aziridinyl)-2,5-cyclohexadiene-1,4-dione
triethyleniminobenzoquinone
bay 3231
2,5-tris(1-aziridino)-p-benzoquinone
triaziquone
triaziquinone
riker 601
2,5-tris(ethylenimino)benzoquinone
2,5-tri(1-aziridinyl)-p-benzoquinone
trisethyleneiminoquinone
2,3,5-tris(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione
trenimone
2,3,5-tris(ethylenimino)benzoquinone
1,1',1''-(3,6-dioxo-1,4-cyclohexadiene-1,2,4-triyl)trisaziridine
2,3,5-tris(1-aziridino)-p-benzoquinone
ai3-51086
triazichon [german]
2,3,5-ethylenimine-1,4-benzoquinone
aziridine, 1,1',1''-(3,6-dioxo-1,4-cyclohexadiene-1,2,4-triyl)tris-
p-benzoquinone, 2,3,5-tris(1-aziridinyl)-
triazicuona [inn-spanish]
einecs 200-692-6
2,3,5-tris-ethyleniminoquinone-(1,4)
2,3,5-tris(aziridinyl)-1,4-benzoquinone
ccris 1288
brn 0238057
2,3,5-tris(ethylenimino)-1,4-benzoquinone
hsdb 7306
2,3,5-tris(ethylenimino)-p-benzoquinone
triaziquonum [inn-latin]
nsc 29215
2,3,5-tris(aziridino)-1,4-benzoquinone
trisaethyleniminobenzochinon [german]
2,3,5-triethyleneimino-1,4-benzoquinone
2,3,5-tri-(1-aziridinyl)-p-benzoquinone
2,3,5-triethyleneimino-p-benzoquinone
2,3,5-tris(1-aziridinyl)-p-benzoquinone
triazoquinone
2,3,5-trisethyleneiminobenzoquinone
tris(aziridinyl)-para-benzoquinone
2,3,5-tris(ethyleneimino)-1,4-benzoquinone
2,3,5-tris(1-aziridinyl)-2,5-cyclohexadiene-1,4-dione
triaziquone [inn:ban]
triaziquinonum
triaziquone (inn)
D07254
2,3, 5-tris(ethyleneimi
2,3, 5-tris(1-aziridino)-p-benzoquinone
2,3,5-tris(aziridin-1-yl)-1,4-benzoquinone
2,3, 5-tris(aziridinyl)-1,4-benzoquinone
2,3, 5-triethyleneimino-p-benzoquinone
1,1',1''-(3,6-dioxo-1,4-cyclohexadiene-1,2, 4-triyl)trisaziridine
2,3,5-tri(1-aziridinyl)benzo-1,4-quinone
C19542
triazicuona
unii-f3d5d9p25i
4-20-00-00031 (beilstein handbook reference)
f3d5d9p25i ,
triaziquonum
triaziquone [mi]
tris(aziridinyl)-para-benzoquinone [iarc]
triaziquone [who-dd]
triaziquone [hsdb]
triaziquone [inn]
SCHEMBL8303
2,3,5-tri(1-aziridinyl)benzo-1,4-quinone #
2,3,5-tris(ethyleneimino)benzoquinone
2,3,5-tri(1-aziridinyl)-p-benzoquinone
DTXSID1021370
2,3,5-tri(aziridin-1-yl)cyclohexa-2,5-diene-1,4-dione
DB13304
Q1323947
oncovedex; prenimon; riker 601; teib; trenimon
CS-0026561
HY-105740
AKOS040754247

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Male and female Drosophila melanogaster with special sex chromosome or special autosome constitutions were fed with the mutagenic chemicals Trenimon (2,3,5-trisethyleneimino-1,4-benzoquinone) and PDMT (1-phenyl-3, 3-dimethyltriazene) and with the toxic substance Na2PO3F (sodium monofluorophosphate)."( Induced dominant lethal mutations and cytotoxic effects in germ cells of Drosophila melanogaster with Trenimon, PDMT and sodium monofluorophosphate.
Büchi, R, 1977
)
0.26

Dosage Studied

ExcerptRelevanceReference
" Also, because the dosage required is comparatively low, patients over procreative age could be included in the program of treatment with immunosuppressants."( [Results and experiences in the immunosuppressive therapy of rheumatoid arthritis].
Keitel, W, 1976
)
0.26
" For both compounds, very similar dose-response curves were found for induction of chromatid breaks in the dose range 10-75 mg/kg."( Transplacental genetic and cytogenetic effects of alkylating agents in the mouse. II. Induction of chromosomal aberrations.
Braun, R; Hüttner, E; Schöneich, J, 1986
)
0.27
"In animal experiments the possibility of increasing the dosage of anticancer drugs by isolated in situ tumor perfusion without incurring systemic toxicity was studied."( The effect of in situ isolated perfusion of experimental renal tumors with cytotoxic agents in high concentration.
Asbach, HW; Bersch, W, 1980
)
0.26
" To date, the kinetics of induction and dose-response relationships of reciprocal translocations induced by chemicals have been little investigated."( Application of chromosome painting to clastogenicity testing in vitro.
Marshall, R; Obe, G, 1998
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
alkylating agentHighly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
aziridines
1,4-benzoquinonesAny member of the class of benzoquinones that is 1,4-benzoquinone or its C-substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID1130141Antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to give maximum increase in life span administered as qd for 12 days1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID19922E1/2 for the half-wave potential at pH=7.0 in V571996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID132973Minimum Effective Dose (MED) which cause 40% increase in life span, after chronic injection at log (1/C).1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Neural networks applied to quantitative structure-activity relationship analysis.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID19426HPLC capacity factor (logK)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1130143Antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to give maximum increase in life span administered for 1 day1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID1130145Antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to give maximum increase in life span administered as continuous injection1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID228714log KGSH for the rate k of glutathione (GSH) consumption in 1/s1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1130144Antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to increase 40% life span administered as continuous injection1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID1130142Antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to increase 40% life span administered for 1 day1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID1130146Chemotherapeutic index, ratio of antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to give maximum increase in life span administered as continuous injection to antileukemic activity against mouse1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID97908log 1/D125 for the dose (mmol/kg) to give 125%T/C ratio (L1210) in vivo1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID1130140Antileukemic activity against mouse L1210 cells allografted in BDF1 mouse assessed as concentration required to increase 40% life span administered as qd for 12 days1979Journal of medicinal chemistry, May, Volume: 22, Issue:5
Quantitative structure-activity relationships in 2,5-bis(1-aziridinyl)-p-benzoquinone derivatives against leukemia L-1210.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID133615Optimal Dose (OD) which cause maximum increase in the life span, after chronic injection at log (1/C).1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Neural networks applied to quantitative structure-activity relationship analysis.
AID94809In vitro cytotoxicity tested against human chronic leukemia K562 cells1997Journal of medicinal chemistry, Jan-31, Volume: 40, Issue:3
Cross-linking and sequence specific alkylation of DNA by aziridinyl quinones. 2. Structure requirements for sequence selectivity.
AID97909log 1/ID75 for the in vitro clonogenic L1210 assay with ID75 in umol/L1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID18769Observed rate of hydrolysis (logKobs) (pH=4.0)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID132974Minimum Effective Dose (MED) which cause 40% increase in life span, after singular injection at log (1/C).1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Neural networks applied to quantitative structure-activity relationship analysis.
AID133616Optimal Dose (OD) which cause maximum increase in the life span, after singular injection at log (1/C).1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Neural networks applied to quantitative structure-activity relationship analysis.
AID72099log 1/MIC for fungi in mmol/L1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID19838Partition coefficient (logP)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID228716log 1/anion production.1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID235150Selectivity for 5`-TGC sites for reduction1997Journal of medicinal chemistry, Jan-31, Volume: 40, Issue:3
Cross-linking and sequence specific alkylation of DNA by aziridinyl quinones. 2. Structure requirements for sequence selectivity.
AID21056Electrochemically observed pKa (pKred) of aziridines1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID228715log 1/LD50 for LD50 (mmol/kg)1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
AID38961log 1/D125 or the dose (mmol/kg) to give 125%T/C ratio (B16) in vivo1996Journal of medicinal chemistry, Feb-02, Volume: 39, Issue:3
In vivo activity and hydrophobicity of cytostatic aziridinyl quinones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (485)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990471 (97.11)18.7374
1990's11 (2.27)18.2507
2000's2 (0.41)29.6817
2010's1 (0.21)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 15.32

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index15.32 (24.57)
Research Supply Index6.25 (2.92)
Research Growth Index3.95 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (15.32)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (1.37%)5.53%
Reviews17 (3.32%)6.00%
Case Studies10 (1.95%)4.05%
Observational0 (0.00%)0.25%
Other478 (93.36%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]