Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H4N6O |
| Molecular Weight | 152.1142 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=NN2)C(=O)N1
InChI
InChIKey=LPXQRXLUHJKZIE-UHFFFAOYSA-N
InChI=1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
| Molecular Formula | C4H4N6O |
| Molecular Weight | 152.1142 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
8-Azaguanine is a purine analog which resembles guanine close enough to compete with it in the metabolism of living organisms. It has been widely studied and has shown to cause retardation of some malignant neoplasms when administered to tumors in animals. It has been used for the treatment of patients with leukemia.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structure-based selection of small molecules to alter allele-specific MHC class II antigen presentation. | 2011-12-01 |
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| Detection of pathogenic Leptospira from selected environment in Kelantan and Terengganu, Malaysia. | 2010-12 |
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| Changes in lipid and carnitine concentrations following repeated fasting-refeeding in mice. | 2010-12 |
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| Ethyl 1-benzyl-5-{[(isopropyl-amino)(3-nitro-phen-oxy)methyl-idene]amino}-1H-1,2,3-triazole-4-carboxyl-ate. | 2010-11-17 |
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| 3-Benzyl-6-butyl-5-propyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one. | 2010-11-13 |
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| 6-Butyl-5-(4-methyl-phen-oxy)-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one. | 2010-10-31 |
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| 6-Isopropyl-5-meth-oxy-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one. | 2010-10-30 |
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| FlaB PCR-based identification of pathogenic leptospiral isolates. | 2010-02 |
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| Mutagenicity of Chinese traditional medicine Semen Armeniacae amarum by two modified Ames tests. | 2009-11-15 |
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| 6-Butyl-5-(4-methoxy-phen-oxy)-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one. | 2009-11-07 |
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| Intersystem crossing to excited triplet state of aza analogues of nucleic acid bases in acetonitrile. | 2009-11-05 |
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| Development and characterization of HAT-sensitive Ewing tumour cells for immunotherapy. | 2009-11 |
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| 3-Benzyl-6-isopropyl-5-phen-oxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one. | 2009-10-17 |
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| 6-Isopropyl-3-phenyl-5-(p-tol-yloxy)-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one: whole-mol-ecule disorder. | 2009-10-07 |
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| 5-(4-Chloro-phen-oxy)-6-isopropyl-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one. | 2009-09-30 |
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| Direct measurement of the ionization state of an essential guanine in the hairpin ribozyme. | 2009-05 |
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| Leptospira kmetyi sp. nov., isolated from an environmental source in Malaysia. | 2009-04 |
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| AtAzg1 and AtAzg2 comprise a novel family of purine transporters in Arabidopsis. | 2009-01-22 |
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| Semi-allogeneic vaccines and tumor-induced immune tolerance. | 2009-01-08 |
|
| Leptospira wolffii sp. nov., isolated from a human with suspected leptospirosis in Thailand. | 2008-10 |
|
| Leptospira weilii serovar Topaz, a new member of the Tarassovi serogroup isolated from a bovine source in Queensland, Australia. | 2008-10 |
|
| Human leptospirosis caused by a new, antigenically unique Leptospira associated with a Rattus species reservoir in the Peruvian Amazon. | 2008-04-02 |
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| Gene targeting in adult rhesus macaque fibroblasts. | 2008-03-26 |
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| Enhancement of hybridoma formation, clonability and cell proliferation in a nanoparticle-doped aqueous environment. | 2008-01-14 |
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| Semi-allogeneic vaccine for T-cell lymphoma. | 2007-08-08 |
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| CD26/DPPIV expression and 8-azaguanine response in T-acute lymphoblastic leukaemia cell lines in culture. | 2007-05 |
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| 8-Azaguanine reporter of purine ionization states in structured RNAs. | 2007-03-21 |
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| Interactions of calf spleen purine nucleoside phosphorylase with formycin B and its aglycone - spectroscopic and kinetic studies. | 2007 |
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| Lead compounds for antimalarial chemotherapy: purine base analogs discriminate between human and P. falciparum 6-oxopurine phosphoribosyltransferases. | 2006-12-14 |
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| Identification of pathogenic Leptospira species by conventional or real-time PCR and sequencing of the DNA gyrase subunit B encoding gene. | 2006-10-27 |
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| Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006-07-26 |
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| Expression of the E. coli fpg protein in CHO cells lowers endogenous oxypurine clustered damage levels and decreases accumulation of endogenous Hprt mutations. | 2006-06 |
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| Structure of human PNP complexed with ligands. | 2005-07 |
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| Spectroscopic and kinetic studies of interactions of calf spleen purine nucleoside phosphorylase with 8-azaguanine, and its 9-(2-phosphonylmethoxyethyl) derivative. | 2005 |
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| Interactions of calf spleen purine nucleoside phosphorylase with 8-azaguanine, and a bisubstrate analogue inhibitor: implications for the reaction mechanism. | 2004-11-16 |
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| A unique strain of Leptospira isolated from a patient with pulmonary haemorrhages in the Andaman Islands: a proposal of serovar portblairi of serogroup Sehgali. | 2004-08 |
|
| [A study on inclusion complexes of cyclodextrin with three anticancer xanthines by fluorescence]. | 2004-07 |
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| Estimation of guanine deaminase using guanosine as a "prosubstrate". | 2004-01-15 |
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| Chemical composition of some components of the arrestment pheromone of the black-legged tick, Ixodes scapularis (Acari: Ixodidae) and their use in tick control. | 2003-11 |
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| Spectroscopy behavior of 6-Mercaptopurine, Azathiopurine, and 8-Azaguanine. | 2003-11 |
|
| Genetic engineering of Escherichia coli for production of tetrahydrobiopterin. | 2003-10 |
|
| Structure and the energy of base pairing in non-natural bases of nucleic acids: the azaguanine-cytosine and azaadenine-thymine base pairs. | 2003-10 |
|
| Characterisation of methionine adenosyltransferase from Mycobacterium smegmatis and M. tuberculosis. | 2003-06-16 |
|
| The yeast ISN1 (YOR155c) gene encodes a new type of IMP-specific 5'-nucleotidase. | 2003-05-07 |
|
| Response of human REV3 gene to gastric cancer inducing carcinogen N-methyl-N'-nitro-N-nitrosoguanidine and its role in mutagenesis. | 2003-05 |
|
| Fusion of mature dendritic cells and human T-lymphotropic virus type I infected T cells: its efficiency as an antigen-presenting cell. | 2002-09-15 |
|
| [Riboflavin overproduction in 4-aminopyrazole[3,4-d]pyrimidine-treated yeast Pichia guilliermondii]. | 2002-06-19 |
|
| Behavioural and chemoreceptor cell responses of the tick, Ixodes ricinus, to its own faeces and faecal constituents. | 2001 |
|
| Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds. | 1997-12-24 |
|
| Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii. | 1995-11-09 |
Patents
Sample Use Guides
8-azaguanine was suspended in a 10 % glucose solution and delivered intravenously. Four patients received a daily dose of 8-azaguanine between 25 to 1000 mg for 4 to 42 days. Two of the four patients with acute leukemia showed a rapid decrease in the leukocyte count and regression in the size of the lymph nodes, liver, and spleen.
Route of Administration:
Intravenous
Human epidermoid carcinoma cells (H.Ep.-2) and Adenocarcinoma-755 cells were maintained in SRI-14 tissue culture medium. Effects of 8-Azaguanine on cellular proliferation were determined by following the increase in cell number over a 72 hour period of exponential growth. Cell viability was determined by measurement of clones formed when approximately 100 H.Ep. 2 cells were cultured in 10 ml of medium over a 7- to 14-day period. Approximately 100 H.Ep. 2 S cells were attached to glass by overnight incubation. The cells were then exposed for 1 hour to 8-azaguanine in the presence or absence of 1 mM thymidine. Cells were washed and viability determined. The viability of H.Ep.-2 cells was limited to 35 % and 21 % of control cultures in the presence and absence of thymidine respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:57:29 GMT 2025
by
admin
on
Mon Mar 31 18:57:29 GMT 2025
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| Record UNII |
Q150359I72
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1556
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63486
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DB01667
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m2159
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134-58-7
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8-AZAGUANINE
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205-148-1
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DTXSID0074508
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C28788
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