NAV

8-azaguanine

Identification

Generic Name
8-azaguanine
DrugBank Accession Number
DB01667
Background

8-azaguanine is one of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 152.1142
Monoisotopic: 152.04465878
Chemical Formula
C4H4N6O
Synonyms
  • 3-amino-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one
  • 8 AG
  • Azaguanine
  • Azaguanine-8
  • Guanazol
  • Pathocidin
  • Pathocidine
External IDs
  • B-28
  • SF-337
  • SK 1150
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with 8-azaguanine.
AbametapirThe serum concentration of 8-azaguanine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of 8-azaguanine can be increased when combined with Abatacept.
AbirateroneThe serum concentration of 8-azaguanine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with 8-azaguanine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as triazolopyrimidines. These are polycyclic aromatic compounds containing triazole ring fused to a pyrimidine ring. Triazole is a five-membered ring consisting of two carbon atoms and three nitrogen atoms. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Triazolopyrimidines
Sub Class
Not Available
Direct Parent
Triazolopyrimidines
Alternative Parents
Hydroxypyrimidines / Triazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
1,2,3-triazole / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyrimidine / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
triazolopyrimidines, nucleobase analogue (CHEBI:63486) / a small molecule (CPD0-1143)
Affected organisms
Not Available

Chemical Identifiers

UNII
Q150359I72
CAS number
134-58-7
InChI Key
LPXQRXLUHJKZIE-UHFFFAOYSA-N
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)
IUPAC Name
5-amino-3H,6H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
SMILES
NC1=NC2=C(N=NN2)C(=O)N1

References

General References
  1. Michels AW, Ostrov DA, Zhang L, Nakayama M, Fuse M, McDaniel K, Roep BO, Gottlieb PA, Atkinson MA, Eisenbarth GS: Structure-based selection of small molecules to alter allele-specific MHC class II antigen presentation. J Immunol. 2011 Dec 1;187(11):5921-30. doi: 10.4049/jimmunol.1100746. Epub 2011 Oct 31. [Article]
PubChem Compound
8646
PubChem Substance
46505914
ChemSpider
8325
BindingDB
96998
ChEBI
63486
ChEMBL
CHEMBL374107
ZINC
ZINC000096321491
PDBe Ligand
AZG
Wikipedia
8-Azaguanine
PDB Entries
1v41 / 4hrq / 4hrw / 7c3s / 7c3t / 7c3u

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)300 °CPhysProp
water solubilityInsolubleNot Available
logP-0.71HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.01 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.1Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)6.5Chemaxon
pKa (Strongest Basic)-2.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area109.05 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity37.11 m3·mol-1Chemaxon
Polarizability12.55 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9848
Blood Brain Barrier+0.9379
Caco-2 permeable-0.5611
P-glycoprotein substrateNon-substrate0.7336
P-glycoprotein inhibitor INon-inhibitor0.9648
P-glycoprotein inhibitor IINon-inhibitor0.9962
Renal organic cation transporterNon-inhibitor0.9382
CYP450 2C9 substrateNon-substrate0.8774
CYP450 2D6 substrateNon-substrate0.8279
CYP450 3A4 substrateNon-substrate0.6789
CYP450 1A2 substrateNon-inhibitor0.8259
CYP450 2C9 inhibitorNon-inhibitor0.8776
CYP450 2D6 inhibitorNon-inhibitor0.8597
CYP450 2C19 inhibitorNon-inhibitor0.8702
CYP450 3A4 inhibitorNon-inhibitor0.834
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9635
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9131
BiodegradationNot ready biodegradable0.9907
Rat acute toxicity2.4904 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.784
hERG inhibition (predictor II)Non-inhibitor0.9205
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0kh9-6900000000-1050694b955262a4b8f6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-965a94e6862d3e1e20c9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-b57b0c89d6da71c239fa
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-3900000000-d423270b2624bc276d70
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-65b4612526e33bbedb90
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gx0-9600000000-a7129650a059c5555495
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-9200000000-8ee36f86bb70dfd51986
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.4280708
predicted
DarkChem Lite v0.1.0
[M-H]-127.2291708
predicted
DarkChem Lite v0.1.0
[M-H]-128.46939
predicted
DeepCCS 1.0 (2019)
[M+H]+126.8527708
predicted
DarkChem Lite v0.1.0
[M+H]+126.9212708
predicted
DarkChem Lite v0.1.0
[M+H]+132.26595
predicted
DeepCCS 1.0 (2019)
[M+Na]+127.5343708
predicted
DarkChem Lite v0.1.0
[M+Na]+127.6688708
predicted
DarkChem Lite v0.1.0
[M+Na]+141.54985
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Purine nucleoside phosphorylase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:51