8-Azaguanine

8-Azaguanine is a purine analog with the chemical formula C4H4N6O. It has been widely studied for its biological activity.[5] It shows antineoplastic activity and has been used in the treatment of acute leukemia.[2]

8-Azaguanine
Names
IUPAC names
5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one;[1]
5-amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;[2]
3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one[3]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.681
RTECS number
  • XZ6157000
UNII
Properties
C4H4N6O
Molar mass 152.117 g·mol−1
Appearance white to off-white crystalline powder[4]
Density 2.64 g/cm³
Melting point > 300 °C (decomp.)
Insoluble
Hazards
Flash point 129.1 °C (264.4 °F; 402.2 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Use in chemotherapy

The compound closely resembles guanine and appears to be competitive with it in the metabolism of living organisms.[6] It has been shown to cause retardation of some malignant neoplasms when administered to tumors in animals.[6] 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice.[7]

Synonyms
* Sources:[3][8][9]

References
  1. "Azaguanine - Compound Summary (Descriptors)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
  2. "8-azaguanine". Mondofacto. 12 December 1998. Retrieved 2009-03-03.
  3. http://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.
  4. "8-AZAGUANINE". ChemicalLAND21.com. Retrieved 2009-03-03.
  5. Tong, George L.; Lee, William W.; Goodman, Leon; Frederiksen, Sune (1965). "Synthesis of some 2′-deoxyribosides of 8-azaadenine". Archives of Biochemistry and Biophysics. University of California: Elsevier. 112 (1): 76. doi:10.1016/0003-9861(65)90012-3.
  6. Colsky, J.; Meiselas, E.L.; Rosen, J.S.; Schulman, I. (1955). "Response of patients with leukemia to 8-azaguanine" (PDF). Blood. 10 (5): 482–92. doi:10.1182/blood.V10.5.482.482. PMID 14363328.
  7. Timmis, G.M.; Williams, Donald Charles (1967). "Chemotherapy of Cancer: the Antimetabolite Approach: The Antimetabolite Approach". University of Michigan: Butterworths: 36. Cite journal requires |journal= (help)
  8. http://www.chemcas.com/msds/cas/msds137/134-58-7.asp Retrieved on 2009-03-03.
  9. "Azaguanine - Compound Summary (Synonyms)". National Center for Biotechnology Information. 27 March 2005. Retrieved 2009-03-03.
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