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
- 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
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPurine nucleoside phosphorylase Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with 8-azaguanine. Abametapir The serum concentration of 8-azaguanine can be increased when it is combined with Abametapir. Abatacept The metabolism of 8-azaguanine can be increased when combined with Abatacept. Abiraterone The serum concentration of 8-azaguanine can be increased when it is combined with Abiraterone. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with 8-azaguanine. Acenocoumarol The metabolism of 8-azaguanine can be decreased when combined with Acenocoumarol. Acetaminophen The metabolism of 8-azaguanine can be decreased when combined with Acetaminophen. Acetazolamide Acetazolamide may increase the excretion rate of 8-azaguanine which could result in a lower serum level and potentially a reduction in efficacy. Acyclovir The metabolism of 8-azaguanine can be decreased when combined with Acyclovir. Adalimumab The serum concentration of 8-azaguanine can be decreased when it is combined with Adalimumab. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- 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]
- External Links
- 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 300 °C PhysProp water solubility Insoluble Not Available logP -0.71 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.01 mg/mL ALOGPS logP -1.4 ALOGPS logP -1.1 ChemAxon logS -1.9 ALOGPS pKa (Strongest Acidic) 6.5 ChemAxon pKa (Strongest Basic) -2.6 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 109.05 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 37.11 m3·mol-1 ChemAxon Polarizability 12.55 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9848 Blood Brain Barrier + 0.9379 Caco-2 permeable - 0.5611 P-glycoprotein substrate Non-substrate 0.7336 P-glycoprotein inhibitor I Non-inhibitor 0.9648 P-glycoprotein inhibitor II Non-inhibitor 0.9962 Renal organic cation transporter Non-inhibitor 0.9382 CYP450 2C9 substrate Non-substrate 0.8774 CYP450 2D6 substrate Non-substrate 0.8279 CYP450 3A4 substrate Non-substrate 0.6789 CYP450 1A2 substrate Non-inhibitor 0.8259 CYP450 2C9 inhibitor Non-inhibitor 0.8776 CYP450 2D6 inhibitor Non-inhibitor 0.8597 CYP450 2C19 inhibitor Non-inhibitor 0.8702 CYP450 3A4 inhibitor Non-inhibitor 0.834 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9635 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9131 Biodegradation Not ready biodegradable 0.9907 Rat acute toxicity 2.4904 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.784 hERG inhibition (predictor II) Non-inhibitor 0.9205
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

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1. DetailsPurine 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
Enzymes
1. DetailsCytochrome 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