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Also known as: 313348-27-5, Lexiscan, Rapiscan, Cvt-3146, Regadenoson anhydrous, 2-[4-[(methylamino)carbonyl]-1h-pyrazol-1-yl]adenosine
Molecular Formula
C15H18N8O5
Molecular Weight
390.35  g/mol
InChI Key
LZPZPHGJDAGEJZ-AKAIJSEGSA-N
FDA UNII
7AXV542LZ4

Regadenoson Monohydrate
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.
Regadenoson anhydrous is a Pharmacologic Cardiac Stress Test Agent. The mechanism of action of regadenoson anhydrous is as an Adenosine Receptor Agonist.
1 2D Structure

Regadenoson Monohydrate

2 Identification
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
2.1.2 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
2.1.3 InChI Key
LZPZPHGJDAGEJZ-AKAIJSEGSA-N
2.1.4 Canonical SMILES
CNC(=O)C1=CN(N=C1)C2=NC(=C3C(=N2)N(C=N3)C4C(C(C(O4)CO)O)O)N
2.1.5 Isomeric 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
2.2 Other Identifiers
2.2.1 UNII
7AXV542LZ4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cvt 3146

2. Cvt-3146

3. Cvt3146

4. Lexiscan

2.3.2 Depositor-Supplied Synonyms

1. 313348-27-5

2. Lexiscan

3. Rapiscan

4. Cvt-3146

5. Regadenoson Anhydrous

6. 2-[4-[(methylamino)carbonyl]-1h-pyrazol-1-yl]adenosine

7. 7axv542lz4

8. Chembl317052

9. 1-(6-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9h-purin-2-yl)-n-methyl-1h-pyrazole-4-carboxamide

10. Adenosine, 2-[4-[(methylamino)carbonyl]-1h-pyrazol-1-yl]-

11. Regadenoson Monohydrate

12. Lexiscan (tn)

13. Cvt 3146

14. Regadenoson [usan:inn]

15. Unii-7axv542lz4

16. Adenosine, 2-(4-((methylamino)carbonyl)-1h-pyrazol-1-yl)-

17. Regadenoson [mi]

18. Regadenoson [inn]

19. Regadenoson (usan/inn)

20. Regadenoson; Cvt-3146

21. Dsstox_cid_31501

22. Dsstox_rid_97386

23. Regadenoson [mart.]

24. Dsstox_gsid_57712

25. Schembl678893

26. Gtpl5596

27. Dtxsid4057712

28. Chebi:135613

29. Hms3886o21

30. Amy27715

31. Ex-a2148

32. Hy-a0168

33. Tox21_113668

34. Bdbm50119132

35. S5358

36. Zinc13818943

37. Akos026750593

38. Ccg-268525

39. Cs-5612

40. Cv-3146

41. Db06213

42. 1-(6-amino-9-beta-d-ribofuranosyl-9h-purin-2-yl)-n-methyl-1h-pyrazole-4-carboxamide

43. Ncgc00249892-01

44. (1-(9-(3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-6-aminopurin-2-yl)pyrazol-4-yl)-n-methylcarboxamide

45. Ac-35838

46. As-56292

47. B5904

48. Cas-313348-27-5

49. Cvt-3146;cvt3146;cvt 3146

50. D05711

51. 348r275

52. J-018384

53. Q7307897

54. (1-{9-[(4s,2r,3r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-n-methylcarboxamide

55. 1-[6-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9h-purin-2-yl]-1h-pyrazole-4-carboxylic Acid Methylamide

56. 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

57. 6-amino-2-[4-(methylcarbamoyl)-1h-pyrazol-1-yl]purine-9-yl-beta-d-ribofuranoside;1-(6-amino-9-((2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yloxy)-9h-purin-2-yl)-n-methyl-1h-pyrazole-4-carboxamide

2.4 Create Date
2005-08-09
3 Chemical and Physical Properties
Molecular Weight 390.35 g/mol
Molecular Formula C15H18N8O5
XLogP3-1.5
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass390.14001570 g/mol
Monoisotopic Mass390.14001570 g/mol
Topological Polar Surface Area187 Ų
Heavy Atom Count28
Formal Charge0
Complexity587
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameLexiscan
PubMed HealthRegadenoson (Injection)
Drug ClassesDiagnostic Agent, Cardiac Function
Drug LabelRegadenoson is an A2A adenosine receptor agonist that is a coronary vasodilator [see Clinical Pharmacology (12.1)]. Regadenoson is chemically described as adenosine, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]-, monohydrate. Its structural formula...
Active IngredientRegadenoson
Dosage FormSolution
RouteIntravenous
Strength0.4mg/5ml (0.08mg/ml)
Market StatusPrescription
CompanyAstellas

2 of 2  
Drug NameLexiscan
PubMed HealthRegadenoson (Injection)
Drug ClassesDiagnostic Agent, Cardiac Function
Drug LabelRegadenoson is an A2A adenosine receptor agonist that is a coronary vasodilator [see Clinical Pharmacology (12.1)]. Regadenoson is chemically described as adenosine, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]-, monohydrate. Its structural formula...
Active IngredientRegadenoson
Dosage FormSolution
RouteIntravenous
Strength0.4mg/5ml (0.08mg/ml)
Market StatusPrescription
CompanyAstellas

4.2 Drug Indication

Diagnostic agent for radionuclide myocardial perfusion imaging (MPI)


FDA Label


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.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
REGADENOSON ANHYDROUS
5.3.2 FDA UNII
7AXV542LZ4
5.3.3 Pharmacological Classes
Adenosine Receptor Agonists [MoA]; Pharmacologic Cardiac Stress Test Agent [EPC]; Adenosine Receptor Agonist [EPC]; Adenosine Receptor Agonists [MoA]
5.4 ATC Code

C01EB21


C01EB21

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C01 - Cardiac therapy

C01E - Other cardiac preparations

C01EB - Other cardiac preparations

C01EB21 - Regadenoson


5.5 Absorption, Distribution and Excretion

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


Route of Elimination

58% of total regadenoson eliminate is via renal excretion


Volume of Distribution

Central compartment: 11.5 L; Steady state: 78.7 L


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.


5.6 Metabolism/Metabolites

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


5.7 Biological 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


5.8 Mechanism of Action

Regadenoson is an selective low-affinity (Ki= 1.3 M) 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 M). 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.


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[{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q1","strtotime":1611513000,"product":"REGADENOSON ANHYDROUS TEST LIC NO: TL\/AZ\/19\/001900 DT. 23.12.2019 (R&D) (10.05 GRAM \/ 4250\/GRAM USD)","address":"CLARIS CORPORATE HEAD QUARTERS, NR.PARIMAL RAILWAY CROSSING,","city":"ELLISBRIDGE,AHMEDABD,GUJARAT,INDIA","supplier":"ARCHIMICA","supplierCountry":"UNITED STATES","foreign_port":"NEW YORK - JOHN F. K","customer":"BAXTER HEALTHCARE CORPORATION","customerCountry":"INDIA","quantity":"0.01","actualQuantity":"0.01","unit":"KGS","unitRateFc":"4271250","totalValueFC":"43129","currency":"USD","unitRateINR":"315431813","date":"25-Jan-2021","totalValueINR":"3154318.13","totalValueInUsd":"43129","indian_port":"AHMEDABAD AIR","hs_no":"29349990","bill_no":"2485192","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"NEW YORK - JOHN F. K","supplierAddress":"","customerAddress":"CLARIS CORPORATE HEAD QUARTERS, NR.PARIMAL RAILWAY CROSSING,"},{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q2","strtotime":1621017000,"product":"REGADENOSON ANHYDROUS-US19600219","address":"FLAT NO 7536 2ND WING 7TH BLOCK,JA NAPRIYA APARTMENTS ERRAGADDA","city":"HYDERABAD,TELANGANA","supplier":"CURIA","supplierCountry":"UNITED STATES","foreign_port":"LOS ANGELES","customer":"EXTROVIS AG","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"1","unit":"GMS","unitRateFc":"5200","totalValueFC":"5306.5","currency":"USD","unitRateINR":"388700","date":"15-May-2021","totalValueINR":"388700","totalValueInUsd":"5306.5","indian_port":"HYDERABAD AIR","hs_no":"29349990","bill_no":"3961299","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"LOS ANGELES","supplierAddress":"","customerAddress":"FLAT NO 7536 2ND WING 7TH BLOCK,JA NAPRIYA APARTMENTS ERRAGADDA"},{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q4","strtotime":1637865000,"product":"REGADENOSON ANHYDROUS(QTY:34GMS,VALUE:USD 153000)","address":"H.NO. 8-2-337, BESIDE TV9 OFFICE, ROAD NO.3, BANJARA HILLS, Contact N","city":"HYDERABAD","supplier":"CURIA","supplierCountry":"UNITED STATES","foreign_port":"NA","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"0.03","actualQuantity":"0.034","unit":"KGS","unitRateFc":"4500000","totalValueFC":"154291.7","currency":"USD","unitRateINR":"337950000","date":"26-Nov-2021","totalValueINR":"11490300","totalValueInUsd":"154291.7","indian_port":"HYDERABAD AIR","hs_no":"29349990","bill_no":"6421010","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"H.NO. 8-2-337, BESIDE TV9 OFFICE, ROAD NO.3, BANJARA HILLS, Contact N"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1702837800,"product":"REGADENOSON (QTY:123GMS, VALUE: USD 553500)","address":"H.NO. 8-2-337,BESIDE TV9 OFFICE","city":"HYDERABAD ANDHRA PRADESH","supplier":"CURIA","supplierCountry":"UNITED STATES","foreign_port":"CHICAGO O\\'HARE INT\\'L","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"0.12","actualQuantity":"0.123","unit":"KGS","unitRateFc":"4500000","totalValueFC":"560527.2","currency":"USD","unitRateINR":"379350000","date":"18-Dec-2023","totalValueINR":"46660050","totalValueInUsd":"560527.2","indian_port":"Hyderabad Air","hs_no":"29349990","bill_no":"9288765","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"CHICAGO O\\'HARE INT\\'L","supplierAddress":"2460 W BENNETT STREET SPRINGFIELD,MISSOURI 65807 USA United States United States United States United States","customerAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE"}]
25-Jan-2021
18-Dec-2023
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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Average Price
(USD/KGS)
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