This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
6-O-benzylguanine
Accession Number
DB11919
Type
Small Molecule
Groups
Investigational
Description

6-O-benzylguanine has been used in trials studying the treatment of HIV Infection, Adult Gliosarcoma, Adult Glioblastoma, Stage I Adult Hodgkin Lymphoma, and Stage II Adult Hodgkin Lymphoma, among others.

Structure
Thumb
Synonyms
  • O6-benzylguanine
External IDs
NSC-637037
Categories
UNII
01KC87F8FE
CAS number
19916-73-5
Weight
Average: 241.2486
Monoisotopic: 241.096359999
Chemical Formula
C12H11N5O
InChI Key
KRWMERLEINMZFT-UHFFFAOYSA-N
InChI
InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)
IUPAC Name
6-(benzyloxy)-3,9-dihydro-2H-purin-2-imine
SMILES
N=C1NC2=C(N=CN2)C(OCC2=CC=CC=C2)=N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe serum concentration of 6-O-benzylguanine can be increased when it is combined with (R)-warfarin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with 6-O-benzylguanine.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with 6-O-benzylguanine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 6-O-benzylguanine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with 6-O-benzylguanine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with 6-O-benzylguanine.
3,5-diiodothyropropionic acidThe serum concentration of 6-O-benzylguanine can be increased when it is combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with 6-O-benzylguanine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with 6-O-benzylguanine.
5-androstenedioneThe metabolism of 6-O-benzylguanine can be decreased when combined with 5-androstenedione.
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
4578
PubChem Substance
347828250
ChemSpider
4417
BindingDB
5491
ChEMBL
CHEMBL407874
HET
OBG
PDB Entries
3kzz

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentBrain and Central Nervous System Tumors5
1CompletedTreatmentBrain and Central Nervous System Tumors / Cancer of the Ovary / Childhood Germ Cell Tumor / Extragonadal Germ Cell Tumor / Liver Cancer / Neuroblastomas / Renal Cancers / Sarcomas / Unspecified Childhood Solid Tumor, Protocol Specific1
1CompletedTreatmentChildhood Central Nervous System Germ Cell Tumor / Childhood Choroid Plexus Tumor / Childhood Craniopharyngioma / Childhood Ependymoblastoma / Childhood Grade I Meningioma / Childhood Grade II Meningioma / Childhood Grade III Meningioma / Childhood High-grade Cerebellar Astrocytoma / Childhood High-grade Cerebral Astrocytoma / Childhood Infratentorial Ependymoma / Childhood Low-grade Cerebellar Astrocytoma / Childhood Low-grade Cerebral Astrocytoma / Childhood Medulloepithelioma / Childhood Mixed Glioma / Childhood Oligodendroglioma / Childhood Supratentorial Ependymoma / Recurrent Childhood Brain Stem Glioma / Recurrent Childhood Cerebellar Astrocytoma / Recurrent Childhood Cerebral Astrocytoma / Recurrent Childhood Ependymoma / Recurrent Childhood Medulloblastoma / Recurrent Childhood Pineoblastoma / Recurrent Childhood Subependymal Giant Cell Astrocytoma / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor / Recurrent Childhood Visual Pathway and Hypothalamic Glioma1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific2
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus 1 Positive / Stage I Adult Hodgkin Lymphoma / Stage I Adult Non-Hodgkin Lymphoma / Stage II Adult Hodgkin Lymphoma / Stage II Adult Non-Hodgkin Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage III Adult Non-Hodgkin Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Adult Non-Hodgkin Lymphoma1
1SuspendedTreatmentGlioblastoma Multiforme (GBM)1
1TerminatedTreatmentBrain and Central Nervous System Tumors1
1TerminatedTreatmentBrain and Central Nervous System Tumors / Malignant Lymphomas / Unspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentRecurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma1
1TerminatedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1, 2Active Not RecruitingTreatmentAdult Glioblastoma / Adult Gliosarcoma / Glioblastomas / Gliosarcoma1
1, 2CompletedTreatmentRecurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Primary Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage I Cutaneous T-cell Non-Hodgkin Lymphoma / Stage I Mycosis Fungoides and Sezary Syndrome AJCC v7 / Stage II Cutaneous T-cell Non-Hodgkin Lymphoma / Stage II Mycosis Fungoides and Sezary Syndrome AJCC v71
2CompletedTreatmentBrain and Central Nervous System Tumors3
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentMelanoma (Skin)1
2CompletedTreatmentMultiple Myeloma and Plasma Cell Neoplasm1
2CompletedTreatmentSarcomas1
2WithdrawnTreatmentBrain and Central Nervous System Tumors1
3CompletedTreatmentMalignant Neoplasms of Eye, Brain and Other Parts of Central Nervous System1
Not AvailableCompletedTreatmentBrain and Central Nervous System Tumors1
Not AvailableWithdrawnTreatmentAdult Nasal Type Extranodal NK/T-Cell Lymphoma / AIDS-Related Diffuse Large Cell Lymphoma / AIDS-Related Diffuse Mixed Cell Lymphoma / AIDS-Related Diffuse Small Cleaved Cell Lymphoma / AIDS-related Immunoblastic Large Cell Lymphoma / AIDS-Related Lymphoblastic Lymphoma / AIDS-related Peripheral/Systemic Lymphoma / AIDS-related Small Noncleaved Cell Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Cutaneous B-Cell Non-Hodgkin Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Hepatosplenic T-Cell Lymphoma / HIV-associated Hodgkin Lymphoma / Intraocular Lymphoma / Nodal marginal zone B-cell lymphomas / Noncutaneous Extranodal Lymphoma / Peripheral T-Cell Lymphoma (PTCL) / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Grade III Lymphomatoid Granulomatosis / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Refractory Hairy Cell Leukemia / Small Intestine Lymphoma / Splenic Marginal Zone Lymphoma / Stage I AIDS-related Lymphoma / Stage II AIDS-related Lymphoma / Stage III AIDS-related Lymphoma / Stage IV AIDS-related Lymphoma / T-Cell Large Granular Lymphocyte Leukemia / Testicular Lymphoma / Waldenström's Macroglobulinemia (WM)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
logP0.9ALOGPS
logP1.39ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.86ChemAxon
pKa (Strongest Basic)5.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.15 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.97 m3·mol-1ChemAxon
Polarizability24.55 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-9511000001-e6a03ce9bd4d7464a377

Taxonomy

Description
This compound belongs to the class of organic compounds known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Hypoxanthines
Alternative Parents
Aminopyrimidines and derivatives / Alkyl aryl ethers / Benzene and substituted derivatives / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Hypoxanthine / Alkyl aryl ether / Aminopyrimidine / Monocyclic benzene moiety / Pyrimidine / Benzenoid / Azole / Imidazole / Heteroaromatic compound / Ether
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
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 performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Roy SK, Korzekwa KR, Gonzalez FJ, Moschel RC, Dolan ME: Human liver oxidative metabolism of O6-benzylguanine. Biochem Pharmacol. 1995 Oct 26;50(9):1385-9. [PubMed:7503788]

Drug created on October 20, 2016 15:00 / Updated on November 02, 2018 07:17