Structure via PubChem · Public domain (PubChem)
8-azaguanine
Sign in to saveAlso known as Azaguanine, Azaguanine-8, Guanazol, Pathocidin, Pathocidine, 3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one, Guanazolo, 5-amino-1H-triazolo[4,5-d]pyrimidin-7-ol
8-Azaguanine is a purine analog with the chemical formula C4H4N6O. It has been widely studied for its biological activity. It shows antineoplastic activity and has been used in the treatment of acute leukemia.
Chemical data
- Formula
- C4H4N6O
- Molecular weight
- 152.11 g/mol
- IUPAC name
- 5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one
- SMILES
- C12=NNNC1=NC(=NC2=O)N
- InChIKey
- LPXQRXLUHJKZIE-UHFFFAOYSA-N
- XLogP
- -0.9
- Polar surface area
- 104 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,135 papers- Tautomeric equilibrium and spectroscopic properties of 8-azaguanine revealed by quantum chemistry methods.European biophysics journal : EBJ · 2023
- Direct potentiation of NK cell cytotoxicity by 8-azaguanine with potential antineoplastic activity.International immunopharmacology · 2019
- 8-Azaguanine resistance in mammalian cells. I. Hypoxanthine-guanine phosphoribosyltransferase.Genetics · 1972
- 8-Azaguanine reporter of purine ionization states in structured RNAs.Journal of the American Chemical Society · 2007
- Platinum-induced mutations to 8-azaguanine resistance in Chinese hamster ovary cells.Mutation research · 1979
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 152.045
Show 2 more facts
- chemical formula
- C₄H₄N₆O
- canonical SMILES
- C12=NNNC1=NC(=NC2=O)N
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Use in chemotherapy
- Synonyms
- References
- External links
8-Azaguanine is a purine analog with the chemical formula C4H4N6O. It has been widely studied for its biological activity. It shows antineoplastic activity and has been used in the treatment of acute leukemia.
==Use in chemotherapy== The compound closely resembles guanine and appears to be competitive with it in the metabolism of living organisms. It has been shown to cause retardation of some malignant neoplasms when administered to tumors in animals. 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice.
Excerpted from Wikipedia’s “8-azaguanine” article, available under the CC BY-SA 4.0 licence.