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Lexiscan

PubChem CID
44154280
Structure
Lexiscan_small.png
Lexiscan_3D_Structure.png
Molecular Formula
Synonyms
  • Regadenoson hydrate
  • Lexiscan
  • 875148-45-1
  • Regadenoson monohydrate
  • UNII-2XLN4Y044H
Molecular Weight
408.37 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2009-08-20
  • Modify:
    2025-01-18
Description
Regadenoson is an Adenosine Receptor Agonist. The mechanism of action of regadenoson is as an Adenosine Receptor Agonist.
Regadenoson is an adenosine derivative and selective A2A adenosine receptor agonist with coronary vasodilating activity. Upon administration, regadenoson selectively binds to and activates the A2A adenosine receptor, which induces coronary vasodilation. This leads to an increase in coronary blood flow and enhances myocardial perfusion. Compared to adenosine, regadenoson has a longer half-life and shows higher selectivity towards the A2A adenosine receptor. This agent is a very weak agonist for the A1 adenosine receptor and has negligible affinity for the A2B and A3 adenosine receptors.
REGADENOSON is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 2008 and is indicated for cardiovascular disease.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Lexiscan.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-N-methylpyrazole-4-carboxamide;hydrate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

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
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

CDQVVPUXSPZONN-WPPLYIOHSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CNC(=O)C1=CN(N=C1)C2=NC(=C3C(=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)N.O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H20N8O6
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

875148-45-1

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 NCI Thesaurus Code

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • CVT 3146
  • CVT-3146
  • CVT3146
  • Lexiscan
  • regadenoson

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
408.37 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
408.15058039 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
408.15058039 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
187 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
29
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
587
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Breast Feeding; Lactation; Adenosine A2 Receptor Agonists; Diagnostic Agents; Purines; Pyrazoles;
Human drug -> Prescription
Human drugs -> Cardiac therapy -> Human pharmacotherapeutic group -> EMA Drug Category

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

This medicinal product is for diagnostic use only. Rapiscan is a selective coronary vasodilator for use as a pharmacological stress agent for radionuclide myocardial perfusion imaging (MPI) in adult patients unable to undergo adequate exercise stress.

6.2 Drug Classes

Breast Feeding; Lactation; Adenosine A2 Receptor Agonists; Diagnostic Agents; Purines; Pyrazoles;

6.3 Clinical Trials

6.3.1 ClinicalTrials.gov

6.3.2 EU Clinical Trials Register

6.4 EMA Drug Information

Medicine
Category
Human drugs
Therapeutic area
Myocardial Perfusion Imaging
Active Substance
regadenoson
INN/Common name
regadenoson
Pharmacotherapeutic Classes
Cardiac therapy
Status
This medicine is authorized for use in the European Union
Company
GE Healthcare AS 
Market Date
2010-09-06

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Adenosine A2 Receptor Agonists
Compounds that selectively bind to and activate ADENOSINE A2 RECEPTORS. (See all compounds classified as Adenosine A2 Receptor Agonists.)

7.2 FDA Pharmacological Classification

FDA UNII
2XLN4Y044H
Active Moiety
REGADENOSON
Pharmacological Classes
Established Pharmacologic Class [EPC] - Adenosine Receptor Agonist
Pharmacological Classes
Mechanisms of Action [MoA] - Adenosine Receptor Agonists
FDA Pharmacology Summary
Regadenoson is an Adenosine Receptor Agonist. The mechanism of action of regadenoson is as an Adenosine Receptor Agonist.

7.3 ATC Code

C01EB21

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

Human drugs -> Cardiac therapy -> Human pharmacotherapeutic group -> EMA Drug Category

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

H310 (50%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H330 (50%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (25%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H370 (25%): Causes damage to organs [Danger Specific target organ toxicity, single exposure]

Precautionary Statement Codes

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P308+P316, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 2 (50%)

Acute Tox. 4 (50%)

Acute Tox. 1 (50%)

Acute Tox. 4 (50%)

Skin Irrit. 2 (50%)

Eye Irrit. 2 (50%)

Acute Tox. 2 (50%)

Acute Tox. 4 (50%)

STOT SE 3 (25%)

STOT SE 1 (25%)

10 Toxicity

10.1 Toxicological Information

10.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the use of regadenoson during breastfeeding. To avoid exposure of the infant to regadenoson, nursing mothers should avoid breastfeeding for 10 hours after drug administration.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Chemical Co-Occurrences in Literature

12.4 Chemical-Gene Co-Occurrences in Literature

12.5 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 Chemical Co-Occurrences in Patents

13.3 Chemical-Disease Co-Occurrences in Patents

13.4 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 KEGG: ATC

15.4 KEGG: Target-based Classification of Drugs

15.5 FDA Pharm Classes

15.6 ChemIDplus

15.7 UN GHS Classification

15.8 EPA DSSTox Classification

15.9 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    1-(6-Amino-9-beta-D-ribofuranosyl-9H-purin-2-yl)-N-methyl-1H-pyrazole-4-carboxamide, monohydrate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.224.514
    1-(6-Amino-9-beta-D-ribofuranosyl-9H-purin-2-yl)-N-methyl-1H-pyrazole-4-carboxamide, monohydrate (EC: 695-796-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/230637
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  7. Drugs and Lactation Database (LactMed)
  8. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  10. EU Clinical Trials Register
  11. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  12. FDA Pharm Classes
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  13. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  14. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  15. Wikidata
  16. PubChem
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Adenosine A2 Receptor Agonists
    https://www.ncbi.nlm.nih.gov/mesh/68058908
  18. GHS Classification (UNECE)
  19. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS