Regadenoson

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Regadenoson (DB06213)

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Weight

Average: 390.354
Monoisotopic: 390.140015726

Chemical Formula

C₁₅H₁₈N₈O₅

Synonyms

• Regadenoson
• Regadenoson anhydrous

External IDs

• CVT-3146

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Pharmacology

Indication

Diagnostic agent for radionuclide myocardial perfusion imaging (MPI)

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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.

Target	Actions	Organism
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;

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Aminophylline	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.

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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 US, Inc.	2008-04-10	Not applicable
Lexiscan(r) (regadenoson)	Injection, solution	0.08 mg/1mL	Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2019-12-10	Not applicable
Rapiscan	Injection, solution	400 mcg	Intravenous	Ge Healthcare As	2020-12-20	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Regadenoson	Injection, solution	0.08 mg/1mL	Intravenous	Hikma Pharmaceuticals USA Inc.	2023-04-03	Not applicable
Regadenoson	Injection	0.08 mg/1mL	Intravenous	Eugia US LLC	2022-10-26	Not applicable
Regadenoson	Injection	0.4 mg/5mL	Intravenous	Mylan Institutional LLC	2023-09-21	Not applicable
Regadenoson	Injection	0.08 mg/1mL	Intravenous	Dr. Reddy's Laboratories Inc.	2023-04-23	Not applicable
Regadenoson	Injection, solution	0.08 mg/1mL	Intravenous	Apotex Corp.	2023-03-10	Not applicable

Categories

ATC Codes

C01EB21 — Regadenoson

• C01EB — Other cardiac preparations
• C01E — OTHER CARDIAC PREPARATIONS
• C01 — CARDIAC THERAPY
• C — CARDIOVASCULAR SYSTEM

Drug Categories

• Adenosine A receptor agonists
• Adenosine A2 Receptor Agonists
• Cardiac Therapy
• Heterocyclic Compounds, Fused-Ring
• Neurotransmitter Agents
• Pharmacologic Cardiac Stress Test Agent
• Purinergic Agents
• Purinergic Agonists
• Purinergic P1 Receptor Agonists

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 / Secondary alcohols / Amino acids and derivatives / Secondary carboxylic acid amides / Azacyclic compounds / Oxacyclic compounds / Organic oxides / Primary amines / Hydrocarbon derivatives / Organopnictogen compounds / Primary alcohols

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Substituents

6-aminopurine / Alcohol / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carboxamide group / Carboxylic acid derivative / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazopyrimidine / Imidolactam / Monosaccharide / N-glycosyl compound / N-substituted imidazole / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Pentose monosaccharide / Primary alcohol / Primary amine / Purine / Purine nucleoside / Pyrazole / Pyrazole-4-carboxamide / Pyrimidine / Secondary alcohol / Secondary carboxylic acid amide / Tetrahydrofuran / Vinylogous amide

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

1. Mitka M: New stress test agents reduce adverse effects. JAMA. 2008 May 14;299(18):2140. doi: 10.1001/jama.299.18.2140. [Article]
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. [Article]
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. [Article]

External Links

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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Diagnostic	Ischaemia	1
4	Completed	Diagnostic	Acute Graft Rejection / Cardiac Transplant / Chronic Graft Rejection	1
4	Completed	Diagnostic	Asthma / Chronic Obstructive Pulmonary Disease (COPD) / Coronary Artery Disease (CAD)	1
4	Completed	Diagnostic	Coronary Artery Disease (CAD)	2
4	Completed	Diagnostic	Coronary Artery Disease (CAD) / Kidney Diseases	1

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
US6642210	No	2003-11-04	2019-06-22
US7144872	No	2006-12-05	2019-06-22
US7183264	No	2007-02-27	2019-06-22
US7582617	No	2009-09-01	2019-06-22
US7655636	No	2010-02-02	2019-06-22
US7655637	No	2010-02-02	2019-06-22
US7683037	No	2010-03-23	2019-06-22
US8106029	No	2012-01-31	2019-06-22
US8183226	No	2012-05-22	2019-06-22
US8536150	No	2013-09-17	2019-06-22
US8470801	No	2013-06-25	2019-06-22
US9289446	No	2016-03-22	2019-06-22
US8106183	No	2012-01-31	2027-02-02
US8133879	No	2012-03-13	2019-06-22
US9085601	No	2015-07-21	2027-02-02
US9045519	No	2015-06-02	2019-06-22
USRE47301	No	2019-03-19	2027-02-02
USRE47351	No	2019-04-16	2019-06-22

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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	predicted	DarkChem Lite v0.1.0
[M-H]-	180.90288	predicted	DeepCCS 1.0 (2019)
[M+H]+	214.9887006	predicted	DarkChem Lite v0.1.0
[M+H]+	183.29843	predicted	DeepCCS 1.0 (2019)
[M+Na]+	212.8485006	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.34206	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1269000	N/A	N/A	A30584
Ki (nM)	1120	N/A	N/A	A30584
Ki (nM)	290	N/A	N/A	A28716

Details

Binding Properties1. 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. [Article]

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Drug created at March 19, 2008 16:17 / Updated at February 21, 2021 18:52