Page last updated: 2024-11-05

guanazole

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

Description

Guanazole is a synthetic purine analog with antiviral and antitumor activity. It is an inhibitor of inosine monophosphate dehydrogenase (IMPDH), an enzyme essential for the synthesis of guanine nucleotides. Guanazole has been studied for its potential therapeutic use in treating various viral infections, including herpes simplex virus (HSV), cytomegalovirus (CMV), and influenza. It has also shown promising results in preclinical studies for the treatment of certain types of cancer, such as leukemia and lymphoma. Guanazole's mechanism of action is based on its ability to compete with guanine for binding to IMPDH, leading to the depletion of guanine nucleotides and inhibition of viral replication. The compound's structure closely resembles guanine, which allows it to readily enter cells and bind to the active site of IMPDH. The importance of guanazole research lies in its potential to provide new therapeutic options for viral infections and cancer. However, further research is needed to evaluate its safety and efficacy in humans.'

Guanazole: A cytostatic triazole derivative which is not to be confused with guanazolo, the generic name for 8-azaguanine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

guanazole : An aromatic amine that is 1,2,4-triazole substituted at positions 3 and 5 by amino 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 CID15078
CHEMBL ID56973
CHEBI ID75425
MeSH IDM0009674

Synonyms (69)

Synonym
BIDD:GT0366
unii-i01twm5267
i01twm5267 ,
nsc-1895
1455-77-2
3,5-diamino-s-triazole
guanazole
1,4-triazolidine, 3,5-diimino-
1h-1,4-triazole-3,5-diamine
nsc1895
nsc 1895
mc 51762
NCI60_001580
3-amino-1h-1,2,4-triazol-5-ylamine
AG-670/31515053
3,5-diamino-1,2,4-triazole
1,2,4-triazolidine-3,5-diimine
1h-1,2,4-triazole-3,5-diamine
nci-c04819
ccris 3745
ai3-51272
guanazole (van)
1,2,4-triazolidine, 3,5-diimino-
einecs 215-937-2
s-triazole, 3,5-diamino-
3,5-diamino-1h-1,2,4-triazole
3,5-diamino-1,2,4-triazole, 98%
nsc-167391
nsc-166592
nsc-167392
4h-1,2,4-triazole-3,5-diamine
STK386290
chebi:75425 ,
CHEMBL56973
3,5-diamino-1h-[1,2,4]triazole
xix ,
FT-0691053
D2587
AKOS000120421
AKOS003234052
BBL001888
dtxsid0025367 ,
cas-1455-77-2
NCGC00260519-01
tox21_202973
dtxcid705367
BP-10410
FT-0614488
guanazole [inci]
2XIX
MB00154
3,5 diamino-1h-1,2,4-triazole
4h-[1,2,4]triazole-3,5-diamine
W-108136
mfcd00005233
503-88-8
Q27145298
SY049252
F15432
3,5-diamino-[1,2,4]triazole
AS-15933
EN300-21450
1h-124-triazole-35-diamine
63598-73-2
guanazole; 3,5-diamino-1,2,4-triazole (guanazole); 3,5-diamino-1h-1,2,4-triazole;3,5-diamino-1,2,4-triazole
A884602
CS-W016656
3,5-diamino-1,2,4-triazole sulfate (2:1)
Z274514098

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"Each of three ribonucleoside diphosphate reductase inhibitors was used as a third drug in combination with selected antitumor platinum (Pt) agents and cyclophosphamide (CY) in the treatment of advanced L1210 leukemia in C57BL/6 x DBA/2 mice."( Schedule-dependency assessments of ribonucleoside diphosphate reductase inhibitors when used in combination with platinum compounds plus cyclophosphamide in the treatment of advanced L1210 leukemia.
Atkins, LM; Gale, GR; Meischen, SJ; Schwartz, P, 1979
)
0.26
" In this research, on-line Raman spectroscopy technique combined with multivariate curve resolution-alternating least squares(MCR-ALS) method was proposed and used to investigate the synthesis mechanism of EMs intermediate (3,5-diamino-1,2,4-triazole, DAT)."( On-line Raman spectroscopy combined with multivariate curve resolution-alternating least squares (MCR-ALS) to investigate the synthesis mechanism of 3,5-diamino-1,2,4-triazole (DAT).
Fu, H; Guo, M; Li, H; Li, M; Tang, H; Zhang, T, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
" Eighteen patients were treated with 5-azacytidine at a dosage of 200-250 mg/m2/day X 5 intravenously (i."( A comparative clinical trial of 5-azacytidine and guanazole in previously treated adults with acute nonlymphocytic leukemia.
Levi, JA; Wiernik, PH, 1976
)
0.51
" All of these drugs were able to induce rapid loss of dhfr gene dosage in the R500 cell population."( Drug-induced loss of unstably amplified genes.
Snapka, RM; Wani, MA, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitorAn EC 1.17.* (oxidoreductase acting on CH or CH2) inhibitor that inhibits the action of ribonucleoside-diphosphate reductase (EC 1.17.4.1).
DNA synthesis inhibitorAny substance that inhibits the synthesis of DNA.
[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
triazolesAn azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.
aromatic amineAn amino compound in which the amino group is linked directly to an aromatic system.
[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]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency15.63680.006038.004119,952.5996AID1159521
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency27.80660.001022.650876.6163AID1224838; AID1224839
progesterone receptorHomo sapiens (human)Potency15.63680.000417.946075.1148AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency27.80660.003041.611522,387.1992AID1159552
retinoid X nuclear receptor alphaHomo sapiens (human)Potency12.52430.000817.505159.3239AID1159527
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency49.44790.001530.607315,848.9004AID1224841
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency31.45970.057821.109761.2679AID1159526
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Proto-oncogene Serine/threonine-protein Kinase Pim-1Homo sapiens (human)IC50 (µMol)5,000.00005,000.00005,000.00005,000.0000AID977608
Chain A, Proto-oncogene Serine/threonine Protein Kinase Pim-1Homo sapiens (human)IC50 (µMol)5,000.00005,000.00005,000.00005,000.0000AID977608
Chain A, Proto-oncogene Serine/threonine Protein Kinase Pim-1Homo sapiens (human)IC50 (µMol)5,000.00005,000.00005,000.00005,000.0000AID977608
Chain A, Proto-oncogene Serine/threonine Protein Kinase Pim-1Homo sapiens (human)IC50 (µMol)5,000.00005,000.00005,000.00005,000.0000AID977608
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID99173Cross resistance profile versus L1210/R71 cells.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Structure-activity relationships of antineoplastic agents in multidrug resistance.
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.
AID23271Partition coefficient (logD7.4)1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Structure-activity relationships of antineoplastic agents in multidrug resistance.
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.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB2011Acta crystallographica. Section D, Biological crystallography, Mar, Volume: 67, Issue:Pt 3
A crystallographic fragment screen identifies cinnamic acid derivatives as starting points for potent Pim-1 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (59.46)18.7374
1990's6 (16.22)18.2507
2000's2 (5.41)29.6817
2010's5 (13.51)24.3611
2020's2 (5.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.13

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 Index24.13 (24.57)
Research Supply Index3.76 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (7.69%)5.53%
Reviews4 (10.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other32 (82.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]