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Revision as of 18:42, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443358942 of page 8-Azaguanine for the Chem/Drugbox validation project (updated: '').  Latest revision as of 23:38, 23 July 2023 edit InternetArchiveBot (talk | contribs)Bots, Pending changes reviewers5,385,671 edits Rescuing 2 sources and tagging 0 as dead.) #IABot (v2.0.9.5 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 443357564 | verifiedrevid = 477226967
| ImageFile = 8-azaguanine.png | ImageFile = 8-azaguanine.png
| ImageSize = 200px | ImageSize = 200px
| IUPACName = 5-amino-2,3-dihydrotriazolopyrimidin-7-one<ref>{{cite web|title=Azaguanine - Compound Summary (Descriptors)|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646#Descriptors|date=27 March 2005|publisher=]|accessdate=2009-03-03}}</ref>;<br />5-amino-1,4-dihydro-7H-1,2,3-triazolopyrimidin-7-one<ref name="mondo">{{cite web|url=http://www.mondofacto.com/facts/dictionary?azaguanine|date=12 December 1998|title=8-azaguanine|publisher=Mondofacto|accessdate=2009-03-03}}</ref>;<br />3-amino-2,4,7,8,9-pentazabicyclonona-1,3,6-trien-5-one<ref name="chemindustry">http://www.chemindustry.com/chemicals/747854.html Retrieved on 2009-03-03.</ref> | IUPACName = 5-amino-2,3-dihydrotriazolopyrimidin-7-one;<ref>{{cite web|title=Azaguanine - Compound Summary (Descriptors)|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646#Descriptors|date=27 March 2005|publisher=]|access-date=2009-03-03}}</ref><br />5-amino-1,4-dihydro-7H-1,2,3-triazolopyrimidin-7-one;<ref name="mondo">{{cite web|url=http://www.mondofacto.com/facts/dictionary?azaguanine|date=12 December 1998|title=8-azaguanine|publisher=Mondofacto|access-date=2009-03-03|archive-date=2010-02-15|archive-url=https://web.archive.org/web/20100215051856/http://mondofacto.com/facts/dictionary?azaguanine|url-status=dead}}</ref><br />3-amino-2,4,7,8,9-pentazabicyclonona-1,3,6-trien-5-one<ref name="chemindustry">{{cite web |url=http://www.chemindustry.com/chemicals/747854.html |title=134-58-7, CAS Number: 3546-41-6 |website=www.chemindustry.com |access-date=2009-03-03 |archive-date=2011-07-16 |archive-url=https://web.archive.org/web/20110716070556/http://www.chemindustry.com/chemicals/747854.html |url-status=dead }}</ref>
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 134-58-7
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8325 | ChemSpiderID = 8325
| EC_number = 205-148-1
⚫ | 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)
| ChEBI = 63486
⚫ | InChIKey = LPXQRXLUHJKZIE-UHFFFAOYAO
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 374107 | ChEMBL = 374107
| DrugBank = DB01667
⚫ | PubChem = 135403646
⚫ | RTECS = XZ6157000
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = Q150359I72
⚫ | 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)
⚫ | InChIKey = LPXQRXLUHJKZIE-UHFFFAOYAO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11) | StdInChI = 1S/C4H4N6O/c5-4-6-2-1(3(11)7-4)8-10-9-2/h(H4,5,6,7,8,9,10,11)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LPXQRXLUHJKZIE-UHFFFAOYSA-N | StdInChIKey = LPXQRXLUHJKZIE-UHFFFAOYSA-N
⚫ | SMILES = C12=NNNC1=NC(=NC2=O)N
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 134-58-7
⚫ | PubChem = 8646
⚫ | RTECS = XZ6157000
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = Q150359I72
⚫ | SMILES = O=C\2\N=C(/N=C1\C/2=N/NN1)N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=4 | H=4 | N=6 | O=1 | C=4 | H=4 | N=6 | O=1
| Appearance = white to off-white crystalline powder<ref>{{cite web|url=http://chemicalland21.com/lifescience/phar/8-AZAGUANINE.htm|title=8-AZAGUANINE|publisher=ChemicalLAND21.com|accessdate=2009-03-03}}</ref> | Appearance = white to off-white crystalline powder<ref>{{cite web|url=http://chemicalland21.com/lifescience/phar/8-AZAGUANINE.htm|title=8-AZAGUANINE|publisher=ChemicalLAND21.com|access-date=2009-03-03}}</ref>
| Density = 2.64 g/cm³ | Density = 2.64 g/cm<sup>3</sup>
| MeltingPt = > 300 °C (''decomp.'') | MeltingPt = > 300 °C (''decomp.'')
| BoilingPt = | BoilingPt =
| Solubility = Insoluble }} | Solubility = Insoluble }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| NFPA-F = | NFPA-H = | NFPA-R = | NFPA-F = | NFPA-H = | NFPA-R =
| MainHazards = | MainHazards =
| FlashPt = 129.1 °C | FlashPtC = 129.1
| Autoignition = }} | AutoignitionPtC = }}
}} }}

'''8-Azaguanine''' is a ] with the ] C<sub>4</sub>H<sub>4</sub>N<sub>6</sub>O. It has been widely studied for its ].<ref>{{Cite journal|author=Tong, George L.|author2=Lee, William W.|author3= Goodman, Leon|author4= Frederiksen, Sune|title=Synthesis of some 2′-deoxyribosides of 8-azaadenine|year=1965|journal=Archives of Biochemistry and Biophysics|volume=112|issue=1|publisher=Elsevier|location=University of California|page=|doi=10.1016/0003-9861(65)90012-3}}</ref> It shows ] activity and has been used in the treatment of ].<ref name="mondo" />

==Use in chemotherapy==
The compound closely resembles ] and appears to be competitive with it in the ] of ]s.<ref name="response">{{Cite journal|author=Colsky, J.|author2=Meiselas, E.L.|author3= Rosen, J.S.|author4= Schulman, I.|year=1955|title=Response of patients with leukemia to 8-azaguanine|journal=Blood|volume=10|issue=5|pages=482–92|pmid=14363328|url=http://bloodjournal.hematologylibrary.org/cgi/reprint/10/5/482.pdf|doi=10.1182/blood.V10.5.482.482|doi-access=free}}</ref> It has been shown to cause retardation of some ] ]s when administered to ]s in animals.<ref name="response" /> 8-Azaguanine was the first purine analogue discovered to inhibit experimental tumors in mice.<ref>{{Cite journal|title=Chemotherapy of Cancer: the Antimetabolite Approach|last1=Timmis|first1=G.M.|last2=Williams|first2=Donald Charles|journal=Butterworths|year=1967|location=University of Michigan|page=36}}</ref>

==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:<ref name="chemindustry" /><ref>{{cite web |url=http://www.chemcas.com/msds/cas/msds137/134-58-7.asp |title=MSDS 7H-v-Triazolo(4,5-d)pyrimidin-7-one,5-amino-1,6-dihydro- CAS 134-58-7 MSDS * 8 AG * 5-Amino-1,6-dihydro-7H-v-triazolo(4,5-d)pyrimidin-7-one * 5-Amino-1,4-dihydro-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one * 5-Amino-7-hydroxy-1H-v-triazolo(d)pyrimidine * 5-Amino-1H-v-triazolo(d)pyrimidin-7-ol * Azaguanine * Azaguanine-8 * 8-Azaguanine * 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- * 7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 5-amino-1,4-dihydro- |website=www.chemcas.com |access-date=2009-03-03}}</ref><ref>{{cite web|title=Azaguanine - Compound Summary (Synonyms)|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8646&ncount=73#Synonyms|date=27 March 2005|publisher=National Center for Biotechnology Information|access-date=2009-03-03}}</ref>''

==References==
<references />

==External links==
*
*
*
* "" on
* "{{Dead link|date=September 2018 |bot=InternetArchiveBot |fix-attempted=yes }}" on the ]
* "" (CID 8646) on ]

{{DEFAULTSORT:Azaguanine, 8-}}
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