8-Azaguanine is a purine analog with the chemical formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 C₄H₄N₆O. It has been widely studied for its biological activity. It shows antineoplastic activity and has been used in the treatment of acute leukemia

Acute leukemia

Acute leukemia or acute leukaemia is a generic term used to describe a family of serious medical conditions relating to an original diagnosis of leukemia...

.

Use in chemotherapy

The compound closely resembles guanine

Guanine

Guanine is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine . In DNA, guanine is paired with cytosine. With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with...

 and appears to be competitive with it in the metabolism

Metabolism

Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...

 of living organisms. It has been shown to cause retardation of some malignant

Malignant

Malignancy is the tendency of a medical condition, especially tumors, to become progressively worse and to potentially result in death. Malignancy in cancers is characterized by anaplasia, invasiveness, and metastasis...

 neoplasms when administered to tumor

Tumor

A tumor or tumour is commonly used as a synonym for a neoplasm that appears enlarged in size. Tumor is not synonymous with cancer...

s in animals. 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice.

Synonyms

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• 2-Amino-6-hydroxy-8-azapurine
• 2-Amino-6-oxy-8-azapurine
• 5-Amino-1,4-dihydro-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one
• 5-Amino-1,6-dihydro-7H-v-triazolo(4,5-d)pyrimidin-7-one
• 5-Amino-1H-triazolo(4,5-d)pyrimidin-7-ol
• 5-Amino-1H-v-triazolo(d)pyrimidin-7-ol
• 5-Amino-1H-(1,2,3)Triazolo(4,5-d)pyrimidin-7-ol
• 5-Amino-7-hydroxy-1H-v-triazolo(d)pyrimidine
• 7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro- (9CI)
• 7H-1,2,3-Triazolo(4,5-d)pyrimidinone, 5-amino-1,4-dihydro-
• 7H-v-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,6-dihydro-
• 8 AG
• 8azaG
• Azaguanine

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• Azaguanine-8
• Azan
• AZG
• B-28
• Guanazol
• Guanazolo
• NSC-749
• Pathocidin
• Pathocidine
• SF-337
• SK 1150
• Triazologuanine
• v-Triazolo(4,5-d)pyrimidin-7-ol,5-amino-

* Sources:

External links

• Digital renderings of the molecule
• Some derivatives and similar molecules
• Web-based 3D viewer with the molecule
• "CAS: 134-58-7" on ChemCAS
• "Azaguanine" on the Merck Index
  Merck Index
  The Merck Index is an encyclopedia of chemicals, drugs and biologicals with over 10,000 monographs on single substances or groups of related compounds. It also includes an appendix with monographs on organic name reactions. It is published by the United States pharmaceutical company Merck & Co...
  
  
• "Azaguanine" (CID 8646) on PubChem
  PubChem
  PubChem is a database of chemical molecules and their activities against biological assays. The system is maintained by the National Center for Biotechnology Information , a component of the National Library of Medicine, which is part of the United States National Institutes of Health . PubChem can...