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8-azaguanine
Identification
- Name
- 8-azaguanine
- Accession Number
- DB01667
- Description
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
Structure for 8-azaguanine (DB01667)
- 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
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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 Unlock Additional DataAbametapir 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. Adenosine The therapeutic efficacy of Adenosine can be decreased when used in combination with 8-azaguanine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
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)
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. [PubMed:22043012]
- 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
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
- 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
- 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]
- 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
- 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 on June 13, 2005 07:24 / Updated on June 12, 2020 10:51
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