Tonapofylline
Identification
- Generic Name
- Tonapofylline
- DrugBank Accession Number
- DB12569
- Background
Tonapofylline has been used in trials studying the treatment of Heart Failure, Renal Insufficiency, and Congestive Heart Failure.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 416.522
Monoisotopic: 416.242355526 - Chemical Formula
- C22H32N4O4
- Synonyms
- Tonapofylline
- External IDs
- BG-9928
- BG9928
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Stimulation of A1 adenosine receptors in the kidney reduces glomerular filtration rate (GFR) via tubuloglomerular feedback and increases sodium reabsorption. Blocking A1 adenosine receptors would therefore maintain GFR and cause natriuresis. Tonapofylline is a xanthine derivative that binds with high affinity to A1 adenosine receptors from several species including human and acts as a competitive antagonist at these receptors.
Target Actions Organism UAdenosine receptor A1 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.Not Available
- Food Interactions
- Not Available
Categories
- 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 / Carbocyclic fatty acids / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds show 7 more
- Substituents
- 6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbocyclic fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acyl show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 83VNU4U44T
- CAS number
- 340021-17-2
- InChI Key
- ZWTVVWUOTJRXKM-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H32N4O4/c1-3-13-25-17-16(18(29)26(14-4-2)20(25)30)23-19(24-17)22-10-7-21(8-11-22,9-12-22)6-5-15(27)28/h3-14H2,1-2H3,(H,23,24)(H,27,28)
- IUPAC Name
- 3-[4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl]propanoic acid
- SMILES
- CCCN1C2=C(NC(=N2)C23CCC(CCC(O)=O)(CC2)CC3)C(=O)N(CCC)C1=O
References
- General References
- Doggrell SA: BG-9928 (Biogen Idec). Curr Opin Investig Drugs. 2005 Sep;6(9):962-8. [Article]
- External Links
- PubChem Compound
- 216466
- PubChem Substance
- 347828791
- ChemSpider
- 187607
- BindingDB
- 50199293
- ChEMBL
- CHEMBL414157
- ZINC
- ZINC000000603777
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Congestive Heart Failure (CHF) / Impaired Renal Function 1 2 Terminated Treatment Heart Failure / Impaired Renal Function 1 1 Completed Not Available Hepatic Impairment 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
Property Value Source Water Solubility 0.118 mg/mL ALOGPS logP 2.74 ALOGPS logP 3.47 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 4.13 Chemaxon pKa (Strongest Basic) -0.69 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 106.6 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 111.71 m3·mol-1 Chemaxon Polarizability 47.37 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001j-0009000000-ae04ad5d3e647816efbe Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0000900000-47e1911b47603ef77739 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0009000000-e48f985a98f5589255d6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01c0-0009500000-f4a514a3607eba90bed0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05cr-0119000000-8b3e0927c0b6d4b539c0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fsr-0219000000-5efa0b8231cba2d99c10 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 219.8659602 predictedDarkChem Lite v0.1.0 [M-H]- 196.71861 predictedDeepCCS 1.0 (2019) [M+H]+ 220.3630602 predictedDarkChem Lite v0.1.0 [M+H]+ 199.07663 predictedDeepCCS 1.0 (2019) [M+Na]+ 219.8725602 predictedDarkChem Lite v0.1.0 [M+Na]+ 205.78679 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Purine nucleoside binding
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- ADORA1
- Uniprot ID
- P30542
- Uniprot Name
- Adenosine receptor A1
- Molecular Weight
- 36511.325 Da
References
- Greenberg B, Thomas I, Banish D, Goldman S, Havranek E, Massie BM, Zhu Y, Ticho B, Abraham WT: Effects of multiple oral doses of an A1 adenosine antagonist, BG9928, in patients with heart failure: results of a placebo-controlled, dose-escalation study. J Am Coll Cardiol. 2007 Aug 14;50(7):600-6. Epub 2007 Jul 30. [Article]
- Vu CB, Kiesman WF, Conlon PR, Lin KC, Tam M, Petter RC, Smits G, Lutterodt F, Jin X, Chen L, Zhang J: Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists. J Med Chem. 2006 Nov 30;49(24):7132-9. [Article]
Drug created at October 20, 2016 22:56 / Updated at February 21, 2021 18:53