Identification

Name
8-azaguanine
Accession Number
DB01667  (EXPT00603)
Type
Small Molecule
Groups
Experimental
Description

One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids. [PubChem]

Structure
Thumb
Synonyms
  • Azaguanine
  • Azaguanine-8
  • Guanazol
  • Pathocidin
  • Pathocidine
External IDs
SF-337
Categories
UNII
Q150359I72
CAS number
134-58-7
Weight
Average: 152.1142
Monoisotopic: 152.04465878
Chemical Formula
C4H4N6O
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-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol
SMILES
NC1=NC2=C(NN=N2)C(O)=N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of 8-azaguanine can be increased when it is combined with (R)-warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with 8-azaguanine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 8-azaguanine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with 8-azaguanine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with 8-azaguanine.
3,5-diiodothyropropionic acidThe serum concentration of 8-azaguanine can be increased when it is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with 8-azaguanine.
6-Deoxyerythronolide BThe metabolism of 8-azaguanine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with 8-azaguanine.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with 8-azaguanine.
Food Interactions
Not Available

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. [PubMed:22043012]
External Links
PubChem Compound
8646
PubChem Substance
46505914
ChemSpider
8325
BindingDB
50200096
ChEBI
63486
ChEMBL
CHEMBL374107
HET
AZG
Wikipedia
8-Azaguanine
PDB Entries
1v41 / 4hrq / 4hrw

Clinical Trials

Clinical Trials
Not Available

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 Solubility5.66 mg/mLALOGPS
logP-0.87ALOGPS
logP-0.16ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)0.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.6 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.24 m3·mol-1ChemAxon
Polarizability12.62 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Triazolopyrimidine / Hydroxypyrimidine / Pyrimidine / Heteroaromatic compound / 1,2,3-triazole / Triazole / Azole / Azacycle / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
triazolopyrimidines, nucleobase analogue (CHEBI:63486) / a small molecule (CPD0-1143)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17139284]
  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. [PubMed:17016423]

Enzymes

Kind
Protein
Organism
Human
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 on June 13, 2005 07:24 / Updated on November 02, 2018 05:04