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

Identification

Generic Name
Rolofylline
DrugBank Accession Number
DB12670
Background

Rolofylline is under clinical development by pharmaceutical company NovaCardia for the treatment of congestive heart failure.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 356.47
Monoisotopic: 356.221226158
Chemical Formula
C20H28N4O2
Synonyms
  • Rolofylline
External IDs
  • KW 3902
  • KW-3902
  • MK-7418

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Rolofylline is an adenosine A1-receptor antagonist. Plasma adenosine levels are elevated in patients with heart failure and adenosine A1 receptors in the kidney mediate vasoconstriction of afferent arterioles, reabsorption of sodium and water in proximal tubules, and tubuloglomerular feedback in the juxtaglomerular apparatus. Accordingly, inhibition of these receptors would be expected to increase renal blood flow and enhance diuresis. The effects of Rolofylline on renal function are consistent with those obtained with another adenosine A1-receptor antagonist in both experimental and human heart failure.

TargetActionsOrganism
UAdenosine receptor A1Not 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
Adverseeffects
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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.
DrugInteraction
AbacavirRolofylline may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AceclofenacRolofylline may increase the excretion rate of Aceclofenac which could result in a lower serum level and potentially a reduction in efficacy.
AcemetacinThe therapeutic efficacy of Rolofylline can be decreased when used in combination with Acemetacin.
AcetaminophenRolofylline may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Rolofylline which could result in a higher serum level.
AclidiniumRolofylline may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
AcrivastineRolofylline may increase the excretion rate of Acrivastine which could result in a lower serum level and potentially a reduction in efficacy.
AcyclovirRolofylline may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy.
Albutrepenonacog alfaRolofylline may increase the excretion rate of Albutrepenonacog alfa which could result in a lower serum level and potentially a reduction in efficacy.
AlclofenacRolofylline may increase the excretion rate of Alclofenac which could result in a lower serum level and potentially a reduction in efficacy.
Interactions
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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 / Pyrimidones / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organooxygen compounds
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Substituents
6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Lactam / Organic nitrogen compound
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
7805S5HIHX
CAS number
136199-02-5
InChI Key
PJBFVWGQFLYWCB-QUYAXPHCSA-N
InChI
InChI=1S/C20H28N4O2/c1-3-5-23-16-15(17(25)24(6-4-2)19(23)26)21-18(22-16)20-10-12-7-13(11-20)9-14(20)8-12/h12-14H,3-11H2,1-2H3,(H,21,22)/t12-,13+,14?,20?
IUPAC Name
1,3-dipropyl-8-[(1R,5S)-tricyclo[3.3.1.0^{3,7}]nonan-3-yl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CCCN1C2=C(NC(=N2)C23C[C@@H]4CC2C[C@H](C3)C4)C(=O)N(CCC)C1=O

References

General References
Not Available
PubChem Compound
11948288
PubChem Substance
347828874
ChemSpider
10122604
ZINC
ZINC000018207215
Wikipedia
Rolofylline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCongestive Heart Failure (CHF)3
2CompletedTreatmentCongestive Heart Failure (CHF) / Deteriorating renal function1
2CompletedTreatmentHeart Failure1

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 Solubility0.125 mg/mLALOGPS
logP4.11ALOGPS
logP3.27ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.83ChemAxon
pKa (Strongest Basic)-0.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.06 m3·mol-1ChemAxon
Polarizability40.66 Å3ChemAxon
Number of Rings5ChemAxon
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

Targets

Drugtargets2
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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

Drug created at October 20, 2016 23:33 / Updated at February 21, 2021 18:53