REGADENOSON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H18N8O5.H2O
Molecular Weight	408.3693
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CNC(=O)C1=CN(N=C1)C2=NC3=C(N=CN3[C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O)C(N)=N2

InChI

InChIKey=CDQVVPUXSPZONN-WPPLYIOHSA-N

InChI=1S/C15H18N8O5.H2O/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);1H2/t7-,9-,10-,14-;/m1./s1

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022161lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/001176/WC500097103.pdf | https://ec.europa.eu/health/documents/community-register/2014/20140116127516/anx_127516_en.pdf | https://www.drugs.com/ppa/regadenoson.html

Regadenoson (Lexiscan), a low affinity agonist of the A2A adenosine receptor, increases coronary blood flow (CBF) and mimics the increase in CBF caused by exercise. Myocardial uptake of the radiopharmaceutical is proportional to CBF creating the contrast required to identify stenotic coronary arteries. It is a pharmacologic stress agent indicated for radionuclide myocardial perfusion imaging (MPI) in patients unable to undergo adequate exercise stress. The most common adverse reactions to Lexiscan are dyspnea, headache, flushing, chest discomfort, dizziness, angina pectoris, chest pain, and nausea. Methylxanthines, e.g., caffeine and theophylline, may interfere with the activity of Lexiscan. Aminophylline may be used to attenuate severe and/or persistent adverse reactions to Lexiscan.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A1 receptor 54 Target ID: CHEMBL226 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022161lbl.pdf	Agonist 2752		16.0 µM [Ki]
Adenosine A2a receptor 31 Target ID: CHEMBL251 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022161lbl.pdf	Agonist 2752		1.3 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Radionuclide myocardial perfusion imaging 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022161lbl.pdf	Diagnostic		Approved 8583	LEXISCAN Approved Use Lexiscan® (regadenoson) injection is a pharmacologic stress agent indicated for radionuclide myocardial perfusion imaging (MPI) in patients unable to undergo adequate exercise stress. Lexiscan is a pharmacologic stress agent indicated for radionuclide myocardial perfusion imaging (MPI) in patients unable to undergo adequate exercise stress (1). Launch Date 2008

C_max

Value	Dose	Co-administered	Analyte	Population
13.6 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/20063904/	400 μg single, intravenous dose: 400 μg route of administration: Intravenous experiment type: SINGLE co-administered:		REGADENOSON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
11.7 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/20063904/	400 μg single, intravenous dose: 400 μg route of administration: Intravenous experiment type: SINGLE co-administered:		REGADENOSON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h REVIEW https://pubmed.ncbi.nlm.nih.gov/20063904/	400 μg single, intravenous dose: 400 μg route of administration: Intravenous experiment type: SINGLE co-administered:		REGADENOSON plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 ug/kg single, intravenous Highest studied dose Dose: 30 ug/kg Route: intravenous Route: single Dose: 30 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Chest pain, Palpitation... Other AEs: Chest pain (1 patient) Palpitation (3 patients) Flushing (3 patients) Shortness of breath (4 patients) Nausea and vomiting (5 patients) Change in ECG (1 patient) Headache (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/
10 ug/kg single, intravenous MTD Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Chest pain, Palpitation... Other AEs: Chest pain (1 patient) Palpitation (3 patients) Dizziness (3 patients) Shortness of breath (1 patient) Nausea and vomiting (2 patients) Headache (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/
10 ug/kg single, intravenous MTD Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Palpitation, Dizziness... Other AEs: Palpitation (4 patients) Dizziness (2 patients) Flushing (4 patients) Shortness of breath (2 patients) Change in ECG (1 patient) Headache (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/
20 ug/kg single, intravenous MTD Dose: 20 ug/kg Route: intravenous Route: single Dose: 20 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Chest pain, Palpitation... Other AEs: Chest pain (1 patient) Palpitation (4 patients) Dizziness (3 patients) Flushing (8 patients) Shortness of breath (3 patients) Nausea and vomiting (3 patients) Change in ECG (7 patients) Headache (7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/
20 ug/kg single, intravenous MTD Dose: 20 ug/kg Route: intravenous Route: single Dose: 20 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Chest pain, Palpitation... Other AEs: Chest pain (2 patients) Palpitation (2 patients) Dizziness (3 patients) Flushing (1 patient) Nausea and vomiting (4 patients) Headache (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/
3 ug/kg single, intravenous Recommended Dose: 3 ug/kg Route: intravenous Route: single Dose: 3 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Chest pain, Palpitation... Other AEs: Chest pain (1 patient) Palpitation (2 patients) Dizziness (1 patient) Flushing (3 patients) Shortness of breath (1 patient) Change in ECG (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/
3 ug/kg single, intravenous Recommended Dose: 3 ug/kg Route: intravenous Route: single Dose: 3 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	healthy, 18-50 years Health Status: healthy Age Group: 18-50 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/	Other AEs: Palpitation, Dizziness... Other AEs: Palpitation (2 patients) Dizziness (1 patient) Flushing (1 patient) Change in ECG (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17112296/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8 1057 CYP2C19 2057	CYP 303

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022161s013lbl.pdf Page: 8.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022161s013lbl.pdf Page: 8.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022161s013lbl.pdf Page: 8.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022161s013lbl.pdf Page: 8.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022161s013lbl.pdf Page: 8.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022161s013lbl.pdf Page: 8.0	no
P-gp 1932	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/27043281/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022161s000_LEXISCAN_CLINPHARM&BIOPHARMR.pdf Page: 18.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022161s000_LEXISCAN_PHARMR.pdf Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00C6IU	https://www.aablocks.com/goods/Goods/detail?id=AA00C6IU
Aaron Chemicals	AR00C7AM	http://www.aaronchem.com/313348-27-5
AbMole Bioscience	M5924	http://www.abmole.com/products/regadenoson.html
Acadechem	ACDS-063067	http://www.acadechemical.com/product/137766
Ambinter	Amb24123241	http://www.ambinter.com/reference/24123241
ApexBio Technology	B5904	http://www.apexbt.com/regadenoson.html
BioCrick	BCC6438	http://www.biocrick.com/Regadenoson-BCC6438.html
BioSynth	J-018384	https://www.biosynth.com/en/products/all-products/products/J-018384.html
BLD Pharm	BD305754	http://www.bldpharm.com/products/313348-27-5.html
Chem Scene	CS-5612	http://www.chemscene.com/313348-27-5.html
ChemMol	49419376	http://www.chemmol.com/chemmol/49419376.html
Chemspace	CSSB00020618037	https://chem-space.com/CSSB00020618037
CSNpharm	CSN15960	https://www.csnpharm.com/products/regadenoson.html
eNovation Chemicals	D501812	http://www.enovationchem.com/productDetails.asp?productID=D501812
eNovation Chemicals	D634242	https://www.enovationchem.com/ProductDetails.asp?ProductID=D634242
eNovation Chemicals	Y0973996	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0973996
Excenen	EX-A2148	https://www.excenen.com/searchresultlist.php?id=313348-27-5
Glentham Life Sciences	GP4974	http://www.glentham.com/products/product/GP4974/
Hairui	HR121254	http://www.hairuichem.com/en/product/313348-27-5.html
iChemical	EBD21504	http://www.ichemical.com/chemicals/cas-313348-27-5
Lab Network	LN02195827	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02195827
MedChem Express	HY-A0168	https://www.medchemexpress.com/Regadenoson.html
OChem	30700	http://www.ocheminc.com/index.php?act=psearch&pid=348R275
Sinfoo Biotech	S047410	http://www.sinfoobiotech.com/product/1050808
Smolecule	S572215	https://www.smolecule.com/products/s572215
THE BioTek	bt-305914	https://www.thebiotek.com/product/others/bt-305914
Wuhan Atomole Chemicals Co., Ltd.	AT-36942	http://www.atomole.com/en/products-view.asp?id=122825
Yuhao Chemical	RT18257	http://www.chemyuhao.com/313348-27-5.html

PubMed

Title	Date	PubMed
Selective adenosine agonists and myocardial perfusion imaging.	2012-02	22130964
New stress test agents reduce adverse effects.	2008-05-14	18477777
Regadenoson, a selective A2A adenosine receptor agonist, causes dose-dependent increases in coronary blood flow velocity in humans.	2007-07	17679059
Adenosine receptors as therapeutic targets.	2006-03	16518376

Patents

Sample Use Guides

In Vivo Use Guide

5 mL (0.4 mg) by rapid injection; followed immediately by saline flush and radiopharmaceutical.

Route of Administration: Intravenous

In Vitro Use Guide

10 nM CVT-3146 decreased coronary perfusion pressure by 23 mm Hg in rat isolated perfused heart.

Name

Type

Language

REGADENOSON

Official Name

English

REGADENOSON MONOHYDRATE

Preferred Name

English

Regadenoson [WHO-DD]

Common Name

English

REGADENOSON MONOHYDRATE [MI]

Common Name

English

RAPISCAN

Brand Name

English

REGADENOSON [VANDF]

Common Name

English

REGADENOSON MONOHYDRATE [MART.]

Common Name

English

REGADENOSON [USAN]

Common Name

English

REGADENOSON HYDRATE [JAN]

Common Name

English

REGADENOSON [ORANGE BOOK]

Common Name

English

ADENOSINE, 2-(4-((METHYLAMINO)CARBONYL)-1H-PYRAZOL-1-YL)-, MONOHYDRATE

Systematic Name

English

REGADENOSON HYDRATE

Common Name

English

LEXISCAN

Brand Name

English

REGADENOSON [EMA EPAR]

Common Name

English

1-(6-AMINO-9-.BETA.-D-RIBOFURANOSYL-9H-PURIN-2-YL)-N-METHYL-1H-PYRAZOLE-4-CARBOXAMIDE, MONOHYDRATE

Common Name

English

CVT-3146

Code

English

Classification Tree Code System Code

NDF-RT

N0000175788