NAV

Propentofylline

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

Identification

Generic Name
Propentofylline
DrugBank Accession Number
DB06479
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 306.3602
Monoisotopic: 306.16919059
Chemical Formula
C15H22N4O3
Synonyms
  • Propentofylline
External IDs
  • HWA 285
  • HWA-285
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Pharmacology

Indication

Investigated for use/treatment in alzheimer's disease.

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Contraindications & Blackbox Warnings
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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 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
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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.
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1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Propentofylline.
AbametapirThe serum concentration of Propentofylline can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Propentofylline can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Propentofylline can be increased when it is combined with Abiraterone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Propentofylline.
Food Interactions
Not Available

Products

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International/Other Brands
Viviq

Categories

ATC Codes
N06BC02 — Propentofylline
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Ketone
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5RTA398U4H
CAS number
55242-55-2
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

References

General References
Not Available
ChemSpider
4769
RxNav
34644
ChEBI
32061
ChEMBL
CHEMBL1079905
ZINC
ZINC000001915505
PDBe Ligand
POY
Wikipedia
Propentofylline
PDB Entries
3arx / 3as2

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility2.72 mg/mLALOGPS
logP1.08ALOGPS
logP1.11Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)19.64Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
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
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-066r-0960000000-8f8228bffbb81a8616c4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0079000000-f252790617400fc8548d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0079000000-98a6568dfaa40f2dead9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-059i-0191000000-3e06128f4afa5e64c13d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0079-0590000000-7fb3a11b1345c56b03c6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3950000000-2ed4b2cce3b4bcb0b78d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-4960000000-9f3cdc0e0d9841504b90
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]-184.1747953
predicted
DarkChem Lite v0.1.0
[M-H]-166.87401
predicted
DeepCCS 1.0 (2019)
[M+H]+184.8231953
predicted
DarkChem Lite v0.1.0
[M+H]+169.23201
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.8502953
predicted
DarkChem Lite v0.1.0
[M+Na]+176.28444
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. cAMP-specific 3',5'-cyclic phosphodiesterase 4A
Kind
Protein
Organism
Humans
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

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
This enzyme listing is based on pharmacokinetic data for methylxanthines as a drug class. Methylxanthines are metabolized by CYP1A2. This drug is a methylxanthine and is therefore assumed to be metabolized by this enzyme.
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
References
  1. Thorn CF, Aklillu E, McDonagh EM, Klein TE, Altman RB: PharmGKB summary: caffeine pathway. Pharmacogenet Genomics. 2012 May;22(5):389-95. doi: 10.1097/FPC.0b013e3283505d5e. [Article]
  2. Buters JT, Tang BK, Pineau T, Gelboin HV, Kimura S, Gonzalez FJ: Role of CYP1A2 in caffeine pharmacokinetics and metabolism: studies using mice deficient in CYP1A2. Pharmacogenetics. 1996 Aug;6(4):291-6. [Article]
  3. Hakooz NM: Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities. Curr Drug Metab. 2009 May;10(4):329-38. [Article]
  4. Rasmussen BB, Brosen K: Determination of urinary metabolites of caffeine for the assessment of cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activity in humans. Ther Drug Monit. 1996 Jun;18(3):254-62. [Article]
  5. Theophylline metabolic pathway [Link]
  6. CYP1A2 activity, gender and smoking, as variables influencing the toxicity of caffeine [File]

Drug created at March 19, 2008 16:34 / Updated at February 21, 2021 18:52