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Experimental cancer drugs
8-Azaguanine
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8-Azaguanine

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8-Azaguanine
8-azaguanine.png
Names
IUPAC names
5-amino-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one;
5-amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one;
3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.681
PubChem CID
RTECS number
  • XZ6157000
UNII
  • 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) checkY
    Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
    Key: LPXQRXLUHJKZIE-UHFFFAOYAO
  • Nc2nc(=O)c1n[nH] [nH]c1n2
Properties
C4H4N6O
Molar mass 152.117 g·mol−1
Appearance white to off-white crystalline powder
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).
checkY verify (what is checkY☒N ?)

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.

Synonyms

  • 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
  • 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


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