Explore a selection of our essential drug information below, or:
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
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APurine nucleoside phosphorylase inhibitorHumans - 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. View sample adverse effects data in our new Data Library!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. - 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 / 8xzq
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.4280708 predictedDarkChem Lite v0.1.0 [M-H]- 127.2291708 predictedDarkChem Lite v0.1.0 [M-H]- 128.46939 predictedDeepCCS 1.0 (2019) [M+H]+ 126.8527708 predictedDarkChem Lite v0.1.0 [M+H]+ 126.9212708 predictedDarkChem Lite v0.1.0 [M+H]+ 132.26595 predictedDeepCCS 1.0 (2019) [M+Na]+ 127.5343708 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.6688708 predictedDarkChem Lite v0.1.0 [M+Na]+ 141.54985 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes 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 (PubMed:23438750, PubMed:9305964). Preferentially acts on 6-oxopurine nucleosides including inosine and guanosine (PubMed:9305964)
- Specific Function
- guanosine phosphorylase activity
- 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. [Article]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22