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Regadenoson

Regadenoson

Synopsis, Chemistry

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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 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

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 Formula	C₁₅H₁₈N₈O₅
Molecular Weight	390.35 g/mol
XLogP3	-1.5
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	4
Exact Mass	390.14001570 g/mol
Monoisotopic Mass	390.14001570 g/mol
Topological Polar Surface Area	187 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	587
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Lexiscan
PubMed Health	Regadenoson (Injection)
Drug Classes	Diagnostic Agent, Cardiac Function
Drug Label	Regadenoson 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 Ingredient	Regadenoson
Dosage Form	Solution
Route	Intravenous
Strength	0.4mg/5ml (0.08mg/ml)
Market Status	Prescription
Company	Astellas

2 of 2
Drug Name	Lexiscan
PubMed Health	Regadenoson (Injection)
Drug Classes	Diagnostic Agent, Cardiac Function
Drug Label	Regadenoson 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 Ingredient	Regadenoson
Dosage Form	Solution
Route	Intravenous
Strength	0.4mg/5ml (0.08mg/ml)
Market Status	Prescription
Company	Astellas

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

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.