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Identification
- Summary
Regadenoson is a coronary vasodilator used in radionuclide myocardial perfusion imaging (MPI).
- Brand Names
- Lexiscan
- Generic Name
- Regadenoson
- DrugBank Accession Number
- DB06213
- Background
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
Structure for Regadenoson (DB06213)
- 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)
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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.
Target Actions Organism AAdenosine receptor A2a agonistHumans - 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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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;
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAminophylline Aminophylline may decrease effectiveness of Regadenoson as a diagnostic agent. Bromotheophylline Bromotheophylline may decrease effectiveness of Regadenoson as a diagnostic agent. Caffeine Caffeine may decrease effectiveness of Regadenoson as a diagnostic agent. Dipyridamole The risk or severity of adverse effects can be increased when Dipyridamole is combined with Regadenoson. Dyphylline Dyphylline may decrease effectiveness of Regadenoson as a diagnostic agent. - 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Regadenoson monohydrate 2XLN4Y044H 875148-45-1 CDQVVPUXSPZONN-WPPLYIOHSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Lexiscan Injection, solution 0.08 mg/1mL Intravenous Astellas Pharma Europe Bv 2008-04-10 Not applicable US 
Lexiscan(r) (regadenoson) Injection, solution 0.08 mg/1mL Intravenous HF Acquisition Co LLC, DBA HealthFirst 2019-12-10 Not applicable US Rapiscan Injection, solution 400 mcg Intravenous Ge Healthcare S.R.L. 2020-12-20 Not applicable EU 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Regadenoson Injection, solution 0.08 mg/1mL Intravenous Almaject, Inc. 2023-07-03 Not applicable US Regadenoson Injection, solution 0.08 mg/1mL Intravenous International Medication Systems, Limited 2023-04-20 Not applicable US Regadenoson Injection, solution 0.08 mg/1mL Intravenous Hospira, Inc. 2023-03-01 Not applicable US Regadenoson Injection, solution 0.08 mg/1mL Intravenous Meitheal Pharmaceuticals Inc. 2022-04-11 Not applicable US Regadenoson Injection, solution 0.08 mg/1mL Intravenous Baxter Healthcare Corporation 2023-05-23 Not applicable US
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
- Affected organisms
- Humans and other mammals
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[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(N)=N1
References
- General References
- Mitka M: New stress test agents reduce adverse effects. JAMA. 2008 May 14;299(18):2140. doi: 10.1001/jama.299.18.2140. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D05711
- PubChem Compound
- 219024
- PubChem Substance
- 175427061
- ChemSpider
- 189859
- BindingDB
- 50119132
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Intravenous 0.08 mg/1mL Injection, solution Intravenous Injection, solution Intravenous 400 mcg Injection Intravenous 0.08 mg/1mL Injection Intravenous 0.4 mg/5mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6403567 No 2002-06-11 2022-04-10 US US6642210 No 2003-11-04 2019-06-22 US US7144872 No 2006-12-05 2019-06-22 US US7183264 No 2007-02-27 2019-06-22 US US7582617 No 2009-09-01 2019-06-22 US US7655636 No 2010-02-02 2019-06-22 US US7655637 No 2010-02-02 2019-06-22 US US7683037 No 2010-03-23 2019-06-22 US US8106029 No 2012-01-31 2019-06-22 US US8183226 No 2012-05-22 2019-06-22 US US8536150 No 2013-09-17 2019-06-22 US US8470801 No 2013-06-25 2019-06-22 US US9289446 No 2016-03-22 2019-06-22 US US8106183 No 2012-01-31 2027-02-02 US US8133879 No 2012-03-13 2019-06-22 US US9085601 No 2015-07-21 2027-02-02 US US9045519 No 2015-06-02 2019-06-22 US USRE47301 No 2019-03-19 2027-02-02 US USRE47351 No 2019-04-16 2019-06-22 US
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.85 mg/mL ALOGPS logP -0.89 ALOGPS logP -2.3 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 12.35 Chemaxon pKa (Strongest Basic) 1.54 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 186.46 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 95.48 m3·mol-1 Chemaxon Polarizability 38.25 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.7551 Caco-2 permeable - 0.7753 P-glycoprotein substrate Non-substrate 0.6036 P-glycoprotein inhibitor I Non-inhibitor 0.9328 P-glycoprotein inhibitor II Non-inhibitor 0.9762 Renal organic cation transporter Non-inhibitor 0.9423 CYP450 2C9 substrate Non-substrate 0.8795 CYP450 2D6 substrate Non-substrate 0.8433 CYP450 3A4 substrate Substrate 0.5052 CYP450 1A2 substrate Non-inhibitor 0.8108 CYP450 2C9 inhibitor Non-inhibitor 0.9275 CYP450 2D6 inhibitor Non-inhibitor 0.9568 CYP450 2C19 inhibitor Non-inhibitor 0.9373 CYP450 3A4 inhibitor Non-inhibitor 0.9626 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9931 Ames test Non AMES toxic 0.6997 Carcinogenicity Non-carcinogens 0.8987 Biodegradation Not ready biodegradable 0.9669 Rat acute toxicity 2.2022 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.964 hERG inhibition (predictor II) Non-inhibitor 0.8999
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-052f-0049000000-8f0ffba4fdeac8518921 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0091000000-67a532d4c38c21f1fe30 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6u-0090000000-34a57b6f96356f421868 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1191000000-af99e0dd12ec91a6e499 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-0090000000-3bd2a55e8b837869153b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0941000000-546efe39367a624217f6 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]- 212.7148006 predictedDarkChem Lite v0.1.0 [M-H]- 180.90288 predictedDeepCCS 1.0 (2019) [M+H]+ 214.9887006 predictedDarkChem Lite v0.1.0 [M+H]+ 183.29843 predictedDeepCCS 1.0 (2019) [M+Na]+ 212.8485006 predictedDarkChem Lite v0.1.0 [M+Na]+ 189.34206 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for adenosine (By similarity). The activity of this receptor is mediated by G proteins which activate adenylyl cyclase (By similarity)
- Specific Function
- alpha-actinin binding
- Gene Name
- ADORA2A
- Uniprot ID
- P29274
- Uniprot Name
- Adenosine receptor A2a
- Molecular Weight
- 44706.925 Da
References
- 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. [Article]
Drug created at March 19, 2008 16:17 / Updated at February 21, 2021 18:52