Regadenoson

Identification

Name
Regadenoson
Accession Number
DB06213
Description

Regadenoson is an A2A adenosine receptor agonist that causes coronary vasodilation and used for myocardial perfusion imagining. Manufactured by Astellas and FDA approved April 10, 2008.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 390.354
Monoisotopic: 390.140015726
Chemical Formula
C15H18N8O5
Synonyms
  • Regadenoson
  • Regadenoson anhydrous
External IDs
  • CVT-3146

Pharmacology

Indication

Diagnostic agent for radionuclide myocardial perfusion imaging (MPI)

Contraindications & Blackbox Warnings
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Pharmacodynamics

Regadenoson rapidly increases coronary blood flow (CBF) which is sustained for a short duration. Mean average peak velocity increased to greater than twice baseline by 30 seconds and decreased to less than twice the baseline level within 10 minutes. Myocardial uptake of the radiopharmaceutical is proportional to (CBF). Regadenoson increases blood flow in normal coronary arteries but not in stenotic (blocked) arteries. The significance of this finding is that stenotic arteries will take up less of the radiopharmaceutical than normal coronary arteries, resulting in a signal that is less intense in these areas.

Mechanism of action

Regadenoson is an selective low-affinity (Ki= 1.3 µM) A2A receptor agonist that mimics the effects of adenosine in causing coronary vasodilatation and increasing myocardial blood flow. It is a very weak agonist of the A1 adenosine receptor (Ki > 16.5 µM). Furthermore, it has negligible affinity to A2B and A3 adenosine receptors. Regadenoson is undergoing trials for use in pharmacological stress tests. Adenosine slows conduction time through the A-V node, can interrupt the reentry pathways through the A-V node, and can restore normal sinus rhythm in patients with paroxysmal supraventricular tachycardia (PSVT), including PSVT associated with Wolff-Parkinson-White Syndrome.

TargetActionsOrganism
AAdenosine receptor A2a
agonist
Humans
Absorption

The pharmacokinetic profile of regadenoson is best described by a 3-compartment model. T max, injection = 1 to 3 minutes; Onset of pharmacodynamic response = 1 to 3 minutes;
E max 12.3 ng/mL

Volume of distribution

Central compartment: 11.5 L; Steady state: 78.7 L

Protein binding
Not Available
Metabolism

The metabolism of regadenoson is unknown in humans. The cytochrome P450 enzyme system is not likely to be involved with the metabolism of regadenoson.

Route of elimination

58% of total regadenoson eliminate is via renal excretion

Half-life

Initial phase: 2-4 minutes; Intermediate phase: 30 minutes (this phase coincides with a loss of the pharmacodynamic effect); Terminal phase: 2 hours

Clearance

Average plasma renal clearance = 450 mL/min. As this value is larger than the glomerular filtration rate, this suggests occurrence of renal tubular secretion.

Adverse Effects
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Toxicity

The most common (incidence ≥ 5%) adverse reactions to regadenoson are dyspnea, headache, flushing, chest discomfort, dizziness, angina pectoris, chest pain, and nausea. MTD (male, supine position): 20 µg/kg; MTD (male, standing position): 10 µg/kg;

Affected organisms
  • Humans and other mammals
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
AminophyllineAminophylline may decrease effectiveness of Regadenoson as a diagnostic agent.
BromotheophyllineBromotheophylline may decrease effectiveness of Regadenoson as a diagnostic agent.
CaffeineCaffeine may decrease effectiveness of Regadenoson as a diagnostic agent.
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Regadenoson.
DyphyllineDyphylline may decrease effectiveness of Regadenoson as a diagnostic agent.
MercaptopurineMercaptopurine may decrease effectiveness of Regadenoson as a diagnostic agent.
OxtriphyllineOxtriphylline may decrease effectiveness of Regadenoson as a diagnostic agent.
PentoxifyllinePentoxifylline may decrease effectiveness of Regadenoson as a diagnostic agent.
TheophyllineTheophylline may decrease effectiveness of Regadenoson as a diagnostic agent.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Avoid caffeine. Do not consume caffeine for at least 12 hours before the administration of regadenoson as caffeine can reduce the ability to detect ischemic changes.

Products

Product Ingredients
IngredientUNIICASInChI Key
Regadenoson monohydrate2XLN4Y044H875148-45-1CDQVVPUXSPZONN-WPPLYIOHSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LexiscanInjection, solution0.08 mg/1mLIntravenousAstellas Pharma US, Inc.2008-04-10Not applicableUS flag
Lexiscan(r) (regadenoson)Injection, solution0.08 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2019-12-10Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
C01EB21 — Regadenoson
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / Pyrazole-4-carboxamides / Aminopyrimidines and derivatives / Imidolactams / N-substituted imidazoles / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds
show 10 more
Substituents
6-aminopurine / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carboxamide group / Carboxylic acid derivative
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
7AXV542LZ4
CAS number
313348-27-5
InChI Key
LZPZPHGJDAGEJZ-AKAIJSEGSA-N
InChI
InChI=1S/C15H18N8O5/c1-17-13(27)6-2-19-23(3-6)15-20-11(16)8-12(21-15)22(5-18-8)14-10(26)9(25)7(4-24)28-14/h2-3,5,7,9-10,14,24-26H,4H2,1H3,(H,17,27)(H2,16,20,21)/t7-,9-,10-,14-/m1/s1
IUPAC Name
1-{6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-N-methyl-1H-pyrazole-4-carboxamide
SMILES
CNC(=O)C1=CN(N=C1)C1=NC2=C(N=CN2[[email protected]@H]2O[[email protected]](CO)[[email protected]@H](O)[[email protected]]2O)C(N)=N1

References

General References
  1. Mitka M: New stress test agents reduce adverse effects. JAMA. 2008 May 14;299(18):2140. doi: 10.1001/jama.299.18.2140. [PubMed:18477777]
  2. Lieu HD, Shryock JC, von Mering GO, Gordi T, Blackburn B, Olmsted AW, Belardinelli L, Kerensky RA: Regadenoson, a selective A2A adenosine receptor agonist, causes dose-dependent increases in coronary blood flow velocity in humans. J Nucl Cardiol. 2007 Jul;14(4):514-20. [PubMed:17679059]
  3. Zoghbi GJ, Iskandrian AE: Selective adenosine agonists and myocardial perfusion imaging. J Nucl Cardiol. 2012 Feb;19(1):126-41. doi: 10.1007/s12350-011-9474-9. [PubMed:22130964]
KEGG Drug
D05711
PubChem Compound
219024
PubChem Substance
175427061
ChemSpider
189859
BindingDB
50119132
RxNav
1546015
ChEBI
135613
ChEMBL
CHEMBL317052
ZINC
ZINC000013818943
PharmGKB
PA166129536
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Regadenoson
FDA label
Download (176 KB)
MSDS
Download (479 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingDiagnosticIschaemia1
4CompletedDiagnosticAcute Graft Rejection / Cardiac Transplant / Chronic Graft Rejection1
4CompletedDiagnosticAsthma / Chronic Obstructive Pulmonary Disease (COPD) / Coronary Artery Disease (CAD)1
4CompletedDiagnosticCoronary Artery Disease (CAD)2
4CompletedDiagnosticCoronary Artery Disease (CAD) / Kidney Diseases1
4CompletedDiagnosticCoronary Artery Disease (CAD) / Type 1 Diabetes Mellitus1
4CompletedDiagnosticDiastolic Heart Failure / Heart Failure, Diastolic / High Blood Pressure (Hypertension)1
4CompletedDiagnosticIschemic Heart Disease1
4CompletedDiagnosticMyocardial Blood Flow Reserve1
4RecruitingDiagnosticCoronary Artery Disease (CAD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntravenous0.08 mg/1mL
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6403567No2002-06-112022-04-10US flag
US6642210No2003-11-042019-06-22US flag
US7144872No2006-12-052019-06-22US flag
US7183264No2007-02-272019-06-22US flag
US7582617No2009-09-012019-06-22US flag
US7655636No2010-02-022019-06-22US flag
US7655637No2010-02-022019-06-22US flag
US7683037No2010-03-232019-06-22US flag
US8106029No2012-01-312019-06-22US flag
US8183226No2012-05-222019-06-22US flag
US8536150No2013-09-172019-06-22US flag
US8470801No2013-06-252019-06-22US flag
US9289446No2016-03-222019-06-22US flag
US8106183No2012-01-312027-02-02US flag
US8133879No2012-03-132019-06-22US flag
US9085601No2015-07-212027-02-02US flag
US9045519No2015-06-022019-06-22US flag
USRE47301No2019-03-192027-02-02US flag
USRE47351No2019-04-162019-06-22US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Liquid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.85 mg/mLALOGPS
logP-0.89ALOGPS
logP-2.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.37ChemAxon
pKa (Strongest Basic)1.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.46 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.48 m3·mol-1ChemAxon
Polarizability37.48 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7551
Caco-2 permeable-0.7753
P-glycoprotein substrateNon-substrate0.6036
P-glycoprotein inhibitor INon-inhibitor0.9328
P-glycoprotein inhibitor IINon-inhibitor0.9762
Renal organic cation transporterNon-inhibitor0.9423
CYP450 2C9 substrateNon-substrate0.8795
CYP450 2D6 substrateNon-substrate0.8433
CYP450 3A4 substrateSubstrate0.5052
CYP450 1A2 substrateNon-inhibitor0.8108
CYP450 2C9 inhibitorNon-inhibitor0.9275
CYP450 2D6 inhibitorNon-inhibitor0.9568
CYP450 2C19 inhibitorNon-inhibitor0.9373
CYP450 3A4 inhibitorNon-inhibitor0.9626
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9931
Ames testNon AMES toxic0.6997
CarcinogenicityNon-carcinogens0.8987
BiodegradationNot ready biodegradable0.9669
Rat acute toxicity2.2022 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.8999
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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

Details
1. Adenosine receptor A2a
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Identical protein binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2A
Uniprot ID
P29274
Uniprot Name
Adenosine receptor A2a
Molecular Weight
44706.925 Da
References
  1. Zoghbi GJ, Iskandrian AE: Selective adenosine agonists and myocardial perfusion imaging. J Nucl Cardiol. 2012 Feb;19(1):126-41. doi: 10.1007/s12350-011-9474-9. [PubMed:22130964]

Drug created on March 19, 2008 10:17 / Updated on June 12, 2020 10:52

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