Jump to section
IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRolofylline
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Name
- Rolofylline
- Accession Number
- DB12670 (DB05360)
- Type
- Small Molecule
- Groups
- Investigational
- Description
Rolofylline is under clinical development by pharmaceutical company NovaCardia for the treatment of congestive heart failure.
- Structure
Structure for DB12670 (Rolofylline)
- Synonyms
- Not Available
- External IDs
- KW 3902 / KW-3902 / MK-7418
- Categories
- UNII
- 7805S5HIHX
- CAS number
- 136199-02-5
- Weight
- Average: 356.47
Monoisotopic: 356.221226158 - Chemical Formula
- C20H28N4O2
- 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[[email protected]@H]4CC2C[[email protected]](C3)C4)C(=O)N(CCC)C1=O
Pharmacology
- Indication
- Not Available
- Structured Indications
- Not Available
- 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.
Target Actions Organism UAdenosine receptor A1 Not Available Human - 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
Drug Interaction Drug group Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Rolofylline. Approved, Illicit Alphacetylmethadol The risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Rolofylline. Experimental, Illicit Alphaprodine The risk or severity of adverse effects can be increased when Alphaprodine is combined with Rolofylline. Illicit Bezitramide The risk or severity of adverse effects can be increased when Bezitramide is combined with Rolofylline. Experimental, Illicit, Withdrawn Buprenorphine The risk or severity of adverse effects can be increased when Buprenorphine is combined with Rolofylline. Approved, Illicit, Investigational, Vet Approved Butorphanol The risk or severity of adverse effects can be increased when Butorphanol is combined with Rolofylline. Approved, Illicit, Vet Approved Carfentanil The risk or severity of adverse effects can be increased when Carfentanil is combined with Rolofylline. Illicit, Vet Approved Codeine The risk or severity of adverse effects can be increased when Codeine is combined with Rolofylline. Approved, Illicit Dextromoramide The risk or severity of adverse effects can be increased when Dextromoramide is combined with Rolofylline. Experimental, Illicit Dextropropoxyphene The risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Rolofylline. Approved, Illicit, Withdrawn Dezocine The risk or severity of adverse effects can be increased when Dezocine is combined with Rolofylline. Approved Dihydrocodeine The risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Rolofylline. Approved, Illicit Dihydroetorphine The risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Rolofylline. Experimental, Illicit Dihydromorphine The risk or severity of adverse effects can be increased when Dihydromorphine is combined with Rolofylline. Experimental, Illicit Diphenoxylate The risk or severity of adverse effects can be increased when Diphenoxylate is combined with Rolofylline. Approved, Illicit DPDPE The risk or severity of adverse effects can be increased when DPDPE is combined with Rolofylline. Investigational Ethylmorphine The risk or severity of adverse effects can be increased when Ethylmorphine is combined with Rolofylline. Approved, Illicit Etorphine The risk or severity of adverse effects can be increased when Etorphine is combined with Rolofylline. Illicit, Vet Approved Fentanyl The risk or severity of adverse effects can be increased when Fentanyl is combined with Rolofylline. Approved, Illicit, Investigational, Vet Approved Heroin The risk or severity of adverse effects can be increased when Heroin is combined with Rolofylline. Approved, Illicit Hydrocodone The risk or severity of adverse effects can be increased when Hydrocodone is combined with Rolofylline. Approved, Illicit Hydromorphone The risk or severity of adverse effects can be increased when Hydromorphone is combined with Rolofylline. Approved, Illicit Ketobemidone The risk or severity of adverse effects can be increased when Ketobemidone is combined with Rolofylline. Approved Levomethadyl Acetate The risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Rolofylline. Approved Levorphanol The risk or severity of adverse effects can be increased when Levorphanol is combined with Rolofylline. Approved Lofentanil The risk or severity of adverse effects can be increased when Lofentanil is combined with Rolofylline. Illicit Meptazinol The risk or severity of adverse effects can be increased when Meptazinol is combined with Rolofylline. Experimental Methadone The risk or severity of adverse effects can be increased when Methadone is combined with Rolofylline. Approved Methadyl Acetate The risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Rolofylline. Approved, Illicit Morphine The risk or severity of adverse effects can be increased when Morphine is combined with Rolofylline. Approved, Investigational Nalbuphine The risk or severity of adverse effects can be increased when Nalbuphine is combined with Rolofylline. Approved Nicomorphine The risk or severity of adverse effects can be increased when Nicomorphine is combined with Rolofylline. Experimental Normethadone The risk or severity of adverse effects can be increased when Normethadone is combined with Rolofylline. Approved, Illicit Opium The risk or severity of adverse effects can be increased when Opium is combined with Rolofylline. Approved, Illicit Oxycodone The risk or severity of adverse effects can be increased when Oxycodone is combined with Rolofylline. Approved, Illicit, Investigational Oxymorphone The risk or severity of adverse effects can be increased when Oxymorphone is combined with Rolofylline. Approved, Investigational, Vet Approved Pentazocine The risk or severity of adverse effects can be increased when Pentazocine is combined with Rolofylline. Approved, Vet Approved Pethidine The risk or severity of adverse effects can be increased when Pethidine is combined with Rolofylline. Approved Phenazocine The risk or severity of adverse effects can be increased when Phenazocine is combined with Rolofylline. Experimental Phenoperidine The risk or severity of adverse effects can be increased when Phenoperidine is combined with Rolofylline. Experimental Piritramide The risk or severity of adverse effects can be increased when Piritramide is combined with Rolofylline. Investigational Remifentanil The risk or severity of adverse effects can be increased when Remifentanil is combined with Rolofylline. Approved Sodium phosphate Rolofylline may increase the nephrotoxic activities of Sodium phosphate. Approved Sufentanil The risk or severity of adverse effects can be increased when Sufentanil is combined with Rolofylline. Approved, Investigational Tapentadol The risk or severity of adverse effects can be increased when Tapentadol is combined with Rolofylline. Approved Tilidine The risk or severity of adverse effects can be increased when Tilidine is combined with Rolofylline. Experimental Tramadol The risk or severity of adverse effects can be increased when Tramadol is combined with Rolofylline. Approved, Investigational - Food Interactions
- Not Available
References
- Synthesis Reference
- Not Available
- General References
- Not Available
- External Links
- ChemSpider
- 10122604
- ATC Codes
- Not Available
- AHFS Codes
- Not Available
- PDB Entries
- Not Available
- FDA label
- Not Available
- MSDS
- Not Available
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Heart Failure, Unspecified 1 3 Completed Treatment Congestive Heart Failure (CHF) 3
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 0.125 mg/mL ALOGPS logP 4.11 ALOGPS logP 3.27 ChemAxon logS -3.4 ALOGPS pKa (Strongest Acidic) 7.83 ChemAxon pKa (Strongest Basic) -0.72 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 69.3 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 99.06 m3·mol-1 ChemAxon Polarizability 40.66 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No 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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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 / Vinylogous amides / Imidazoles / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organooxygen compounds show 3 more
- Substituents
- Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Human
- 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 on October 20, 2016 17:33 / Updated on September 01, 2017 12:23