9-Deazaguanine

Identification

Generic Name
9-Deazaguanine
DrugBank Accession Number
DB04356
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 150.138
Monoisotopic: 150.054160834
Chemical Formula
C6H6N4O
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHypoxanthine-guanine phosphoribosyltransferaseNot AvailableHumans
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
Medicalerrors
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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.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of Benzodiazepine can be decreased when used in combination with 9-Deazaguanine.
AbametapirThe serum concentration of 9-Deazaguanine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of 9-Deazaguanine can be increased when combined with Abatacept.
AbirateroneThe serum concentration of 9-Deazaguanine can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with 9-Deazaguanine.
AcenocoumarolThe metabolism of 9-Deazaguanine can be decreased when combined with Acenocoumarol.
AcetaminophenThe metabolism of 9-Deazaguanine can be decreased when combined with Acetaminophen.
AcetazolamideAcetazolamide may increase the excretion rate of 9-Deazaguanine which could result in a lower serum level and potentially a reduction in efficacy.
AcyclovirThe metabolism of 9-Deazaguanine can be decreased when combined with Acyclovir.
AdalimumabThe serum concentration of 9-Deazaguanine can be decreased when it is combined with Adalimumab.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. 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
Pyrrolopyrimidines
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidines
Alternative Parents
Pyrimidones / Aminopyrimidines and derivatives / Vinylogous amides / Pyrroles / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides
show 1 more
Substituents
Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine (CHEBI:40431)
Affected organisms
Not Available

Chemical Identifiers

UNII
H2O1DD3CAN
CAS number
65996-58-9
InChI Key
FFYPRJYSJODFFD-UHFFFAOYSA-N
InChI
InChI=1S/C6H6N4O/c7-6-9-3-1-2-8-4(3)5(11)10-6/h1-2,8H,(H3,7,9,10,11)
IUPAC Name
2-amino-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one
SMILES
NC1=NC2=C(NC=C2)C(=O)N1

References

Synthesis Reference

Arthur J. Elliott, David A. Walsh, "Process for the preparation of 9-deazaguanine derivatives." U.S. Patent US5650511, issued September, 1990.

US5650511
General References
Not Available
PubChem Compound
100684
PubChem Substance
46508363
ChemSpider
90969
BindingDB
50108005
ChEMBL
CHEMBL367746
ZINC
ZINC000100004977
PDBe Ligand
9DG
PDB Entries
1fsg / 1il4 / 1q2r / 1q2s / 6d9r

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.03 mg/mLALOGPS
logP-0.48ALOGPS
logP-0.5ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.18ChemAxon
pKa (Strongest Basic)5.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.27 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.82 m3·mol-1ChemAxon
Polarizability13.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9845
Blood Brain Barrier+0.9509
Caco-2 permeable-0.5468
P-glycoprotein substrateNon-substrate0.6654
P-glycoprotein inhibitor INon-inhibitor0.9562
P-glycoprotein inhibitor IINon-inhibitor0.9895
Renal organic cation transporterNon-inhibitor0.8841
CYP450 2C9 substrateNon-substrate0.8628
CYP450 2D6 substrateNon-substrate0.7741
CYP450 3A4 substrateNon-substrate0.6764
CYP450 1A2 substrateNon-inhibitor0.7562
CYP450 2C9 inhibitorNon-inhibitor0.9495
CYP450 2D6 inhibitorNon-inhibitor0.8952
CYP450 2C19 inhibitorNon-inhibitor0.8771
CYP450 3A4 inhibitorNon-inhibitor0.9421
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.979
Ames testNon AMES toxic0.6878
CarcinogenicityNon-carcinogens0.9658
BiodegradationNot ready biodegradable0.972
Rat acute toxicity2.3603 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9505
hERG inhibition (predictor II)Non-inhibitor0.9373
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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role...
Gene Name
HPRT1
Uniprot ID
P00492
Uniprot Name
Hypoxanthine-guanine phosphoribosyltransferase
Molecular Weight
24579.155 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. [Article]
  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. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

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 13:24 / Updated on June 12, 2020 16:52