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
CAS Number	134-58-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:63486
ChEMBL	ChEMBL374107 Y
ChemSpider	8325 Y
DrugBank	DB01667
ECHA InfoCard	100.004.681
EC Number	205-148-1
PubChem CID	135403646
RTECS number	XZ6157000
UNII	Q150359I72 Y
CompTox Dashboard (EPA)	DTXSID0074508
InChI 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) Y Key: LPXQRXLUHJKZIE-UHFFFAOYSA-N Y 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
SMILES C12=NNNC1=NC(=NC2=O)N
Properties
Chemical formula	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.)
Solubility in water	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). Y verify (what is YN ?) 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

• 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:^[3][8][9]