NAV

Adefovir

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

Identification

Generic Name
Adefovir
DrugBank Accession Number
DB13868
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 273.1857
Monoisotopic: 273.062690409
Chemical Formula
C8H12N5O4P
Synonyms
  • 9-(2-(phosphonomethoxy)ethyl)adenine
  • 9-(2-phosphonylmethoxyethyl)adenine
  • Adéfovir
  • Adefovir
  • Adefovirum
External IDs
  • GS 0393
  • GS-0393
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ADNA polymerase/reverse transcriptase
inhibitor
HBV-D
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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AbacavirAdefovir may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Adefovir.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Acemetacin is combined with Adefovir.
AcetaminophenAdefovir may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Adefovir.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. 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
6-aminopurines
Alternative Parents
Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Organic phosphonic acids / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organophosphorus compounds / Organooxygen compounds
show 2 more
Substituents
6-aminopurine / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidolactam
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6GQP90I798
CAS number
106941-25-7
InChI Key
SUPKOOSCJHTBAH-UHFFFAOYSA-N
InChI
InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
IUPAC Name
{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid
SMILES
NC1=C2N=CN(CCOCP(O)(O)=O)C2=NC=N1

References

General References
Not Available
ChemSpider
54252
BindingDB
50001103
RxNav
16521
ChEBI
2469
ChEMBL
CHEMBL484
ZINC
ZINC000021297308
PDBe Ligand
5HG
Wikipedia
Adefovir
PDB Entries
2g1a

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentViral Hepatitis B1
4CompletedTreatmentChronic Hepatitis B Infection5
4CompletedTreatmentCompensated Chronic Hepatitis B1
4CompletedTreatmentHepatitis B Associated Hepatocellular Carcinoma1
4TerminatedTreatmentChronic Hepatitis B Infection1

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 Solubility2.02 mg/mLALOGPS
logP-1.8ALOGPS
logP-3.9Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.35Chemaxon
pKa (Strongest Basic)3.75Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area136.38 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity63.12 m3·mol-1Chemaxon
Polarizability23.56 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
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-MSsplash10-007k-5910000000-b080ba968f1869c600c9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-3fb85e00369081c6ca8c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-7190000000-9f0b96959b12798712e5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2390000000-48732dc37e79b1a48aec
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02na-2290000000-8126bdc3de910de2e32e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-1900000000-95bf34e2ed59e7af93d5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-5900000000-3addab8467e239b0b92a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-3fb85e00369081c6ca8c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2390000000-48732dc37e79b1a48aec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fr-7190000000-9f0b96959b12798712e5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-1900000000-95bf34e2ed59e7af93d5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02na-2290000000-8126bdc3de910de2e32e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-5900000000-3addab8467e239b0b92a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.7657678
predicted
DarkChem Lite v0.1.0
[M-H]-148.81084
predicted
DeepCCS 1.0 (2019)
[M-H]-169.7657678
predicted
DarkChem Lite v0.1.0
[M-H]-148.81084
predicted
DeepCCS 1.0 (2019)
[M+H]+169.9257678
predicted
DarkChem Lite v0.1.0
[M+H]+151.18913
predicted
DeepCCS 1.0 (2019)
[M+H]+169.9257678
predicted
DarkChem Lite v0.1.0
[M+H]+151.18913
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.5503678
predicted
DarkChem Lite v0.1.0
[M+Na]+157.26198
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.5503678
predicted
DarkChem Lite v0.1.0
[M+Na]+157.26198
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA polymerase/reverse transcriptase
Kind
Protein
Organism
HBV-D
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Multifunctional enzyme that converts the viral RNA genome into dsDNA in viral cytoplasmic capsids. This enzyme displays a DNA polymerase activity that can copy either DNA or RNA templates, and a ri...
Gene Name
P
Uniprot ID
P24024
Uniprot Name
Protein P
Molecular Weight
93588.765 Da
References
  1. Kock J, Baumert TF, Delaney WE 4th, Blum HE, von Weizsacker F: Inhibitory effect of adefovir and lamivudine on the initiation of hepatitis B virus infection in primary tupaia hepatocytes. Hepatology. 2003 Dec;38(6):1410-8. [Article]

Drug created at July 07, 2017 02:58 / Updated at May 29, 2021 18:15