Page last updated: 2024-10-15

8-azahypoxanthine

Description

8-azahypoxanthine: an antimalarial that inhibits hypoxanthine-guanine-xanthine phosphoribosyltransferase; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

8-azahypoxanthine : A triazolopyrimidine that consists of 1,4-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing an oxo substituent at position 7. [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 CID135410720
CHEMBL ID219416
CHEBI ID136532
SCHEMBL ID1230976
SCHEMBL ID14094281
MeSH IDM0040166

Synonyms (67)

Synonym
ae 200
1h-1,3-triazolo[4,5-d]pyrimidin-7-ol
7-hydroxy-v-triazolo[d]pyrimidine
7h-v-triazolo[4, 1,6-dihydro-
7-hydroxy-1,3,4,6-pentaazaindene
v-triazolo[4,5-d]pyrimidin-7-ol
7h-1,3-triazolo[4,5-d]pyrimidin-7-one, 1,4-dihydro-
1h-v-triazolo[4,5-d]pyrimidin-7-ol
7h-1,2,3-triazolo[4,5-d]pyrimidin-7-one, 1,4-dihydro-
NCI60_001853
3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
8-azahypoxanthine
3,6-dihydrotriazolo[4,5-d]pyrimidin-7-one
2683-90-1
1,4-dihydro-7h-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
azahypoxanthine
CHEBI:136532
1h-1,2,3-triazolo(4,5-d)pyrimidin-7-ol
8-azahx
7-hydroxy-1,2,3,4,6-pentaazaindene
A0555
CHEMBL219416
2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one
3h-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol
3,6-dihydro-7h-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
F2124-0964
F2147-0425
AKOS003272028
NCGC00188261-01
AKOS005206808
ai3-50259
7h-1,2,3-triazolo(4,5-d)pyrimidin-7-one, 3,6-dihydro-
7h-v-triazolo(4,5-d)pyrimidin-7-one, 1,6-dihydro-
einecs 220-244-3
1h-v-triazolo(4,5-d)pyrimidin-7-ol
7-hydroxy-v-triazolo(d)pyrimidine
nsc 22709
7h-1,2,3-triazolo(4,5-d)pyrimidin-7-one, 1,4-dihydro-
v-triazolo(4,5-d)pyrimidin-7-ol
GEO-00241
FT-0621502
7h-1,2,3-triazolo[4,5-d]pyrimidin-7-one,3,6-dihydro-
AKOS015854536
7-hydroxy-3h-[1,2,3]triazolo[4,5-d]pyrimidine
2,2-dibromodiphenylacetylene
DTXSID1062590
SCHEMBL1230976
mfcd08692088
SY019936
TS-00032
1,4-dihydro-7h-[1,2,3]triazolo[4,5-d]pyrimidin-7-one #
W-200265
1h-[1,2,3]triazolo[4,5-d]pyrimidin-7(4h)-one
SCHEMBL14094281
CS-0081731
3h-[1,2,3]triazolo[4,5-d]pyrimidin-7(6h)-one
AKOS028109374
mfcd00005804
7-hydroxy-1,2,3-triazolo[4,5-d]pyrimidine
7-hydroxy-3h-1,2,3-triazolo[4,5-d]pyrimidine
2,6-dihydrotriazolo[4,5-d]pyrimidin-7-one
1h-[1,2,3]triazolo[4,5-d]pyrimidin-7(6h)-one
T70692
AKOS037491874
A877122
3h,6h,7h-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
EN300-235705
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antimalarialA drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
EC 2.4.2.8 (hypoxanthine phosphoribosyltransferase) inhibitorAn EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of hypoxanthine phosphoribosyltransferase (EC 2.4.2.8).
[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
nucleobase analogueA molecule that can substitute for a normal nucleobase in nucleic acids.
triazolopyrimidines
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency14.12540.000811.382244.6684AID686978
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency8.48820.058010.694926.6086AID602310; AID651813
DNA dC->dU-editing enzyme APOBEC-3F isoform aHomo sapiens (human)Potency6.31670.025911.239831.6228AID651814; AID651815
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID274548Antiplasmodial activity against Plasmodium falciparum 3D72006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.
AID274550Inhibition of Plasmodium falciparum HGXPRT at pH 7.42006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.
AID1136398Inhibition of human erythrocyte purine nucleoside phosphorylase assessed as inhibition of guanosine phosphorylysis at 4 umol after 30 mins by orcinol reaction1978Journal of medicinal chemistry, Sep, Volume: 21, Issue:9
Stereoelectronic factors in the binding of substrate analogues and inhibitors to purine nucleoside phosphorylase isolated from human erythrocytes.
AID274562Inhibition of human HGPRT at pH 8.52006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.
AID274563Inhibition of Plasmodium falciparum HGXPRT at pH 8.52006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.
AID274547Inhibition of [3H]hypoxanthine uptake in Plasmodium falciparum 3D72006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.
AID274549Inhibition of human HGPRT at pH 7.42006Journal of medicinal chemistry, Dec-14, Volume: 49, Issue:25
Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (57.14)18.7374
1990's2 (28.57)18.2507
2000's1 (14.29)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]