Identification
Name8-azaguanine
Accession NumberDB01667  (EXPT00603)
TypeSmall Molecule
GroupsExperimental
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
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIQ150359I72
CAS number134-58-7
WeightAverage: 152.1142
Monoisotopic: 152.04465878
Chemical FormulaC4H4N6O
InChI KeyLPXQRXLUHJKZIE-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Purine nucleoside phosphorylaseProteinunknownNot AvailableHumanP00491 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of 8-azaguanine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of 8-azaguanine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with 8-azaguanine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of 8-azaguanine.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of 8-azaguanine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of 8-azaguanine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of 8-azaguanine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with 8-azaguanine.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of 8-azaguanine.Experimental
OuabainOuabain may decrease the cardiotoxic activities of 8-azaguanine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with 8-azaguanine.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of 8-azaguanine.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTriazolopyrimidines
Direct ParentTriazolopyrimidines
Alternative ParentsHydroxypyrimidines / Triazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
SubstituentsTriazolopyrimidine / Hydroxypyrimidine / Pyrimidine / Heteroaromatic compound / 1,2,3-triazole / Triazole / Azole / Azacycle / Organic nitrogen compound / Organic oxygen compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorstriazolopyrimidines, 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 bases and pentose-1-phosphate.
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 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 17:01