Propentofylline

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

Identification

Name
Propentofylline
Accession Number
DB06479
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
HWA 285 / HWA-285
International/Other Brands
Viviq
Categories
UNII
5RTA398U4H
CAS number
55242-55-2
Weight
Average: 306.3602
Monoisotopic: 306.16919059
Chemical Formula
C15H22N4O3
InChI Key
RBQOQRRFDPXAGN-UHFFFAOYSA-N
InChI
InChI=1S/C15H22N4O3/c1-4-8-18-10-16-13-12(18)14(21)19(15(22)17(13)3)9-6-5-7-11(2)20/h10H,4-9H2,1-3H3
IUPAC Name
3-methyl-1-(5-oxohexyl)-7-propyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CCCN1C=NC2=C1C(=O)N(CCCCC(C)=O)C(=O)N2C

Pharmacology

Indication

Investigated for use/treatment in alzheimer's disease.

Pharmacodynamics
Not Available
Mechanism of action

Propentofylline is a xanthine derivative and phosphodiesterase inhibitor with purported neuroprotective effects. It inhibits both phosphodiesterase and adenosine uptake. Phosphodiesterase has shown to associated with age-related memory impairment and Alzheimer's disease. β-Amyloid protein 1–42 (β42) can induce apoptosis in the cultured hippocampal neurons, suggesting that it plays an important role in causing neurodegeneration in Alzheimer's disease. Propentofylline is also capable of activating a cAMP–PKA system, depressing the caspase cascade and modifying Bcl-2 family proteins. Propentofylline blocked both the apoptotic features induced by β42 and further induced an anti-apoptotic protein, Bcl-2. It suggests that the protection of propentofylline on the β42-induced neurotoxicity is caused by enhancing anti-apoptotic action through cAMP–PKA system.

TargetActionsOrganism
UcAMP-specific 3',5'-cyclic phosphodiesterase 4ANot AvailableHuman
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
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Propentofylline.
AcenocoumarolThe serum concentration of Propentofylline can be increased when it is combined with Acenocoumarol.
AcetaminophenThe serum concentration of Propentofylline can be increased when it is combined with Acetaminophen.
AdalimumabThe serum concentration of Propentofylline can be decreased when it is combined with Adalimumab.
AdenosineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Propentofylline.
AlprazolamThe therapeutic efficacy of Alprazolam can be decreased when used in combination with Propentofylline.
AmitriptylineThe serum concentration of Propentofylline can be increased when it is combined with Amitriptyline.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Propentofylline.
AnagrelideThe serum concentration of Propentofylline can be increased when it is combined with Anagrelide.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Propentofylline.
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
4769
ChEBI
32061
ChEMBL
CHEMBL1079905
HET
POY
Wikipedia
Propentofylline
ATC Codes
N06BC02 — Propentofylline
PDB Entries
3arx / 3as2

Clinical Trials

Clinical Trials
Not Available

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 Solubility2.72 mg/mLALOGPS
logP1.08ALOGPS
logP1.11ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area75.51 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity82.79 m3·mol-1ChemAxon
Polarizability33.18 Å3ChemAxon
Number of Rings2ChemAxon
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 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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Ketones / Azacyclic compounds
show 4 more
Substituents
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4A
Uniprot ID
P27815
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Molecular Weight
98142.155 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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 March 19, 2008 10:34 / Updated on August 18, 2018 14:48