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MedKoo Cat#: 318655 | Name: Regadenoson (free base)
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Regadenoson is an A2A adenosine receptor agonist that is a coronary vasodilator that is commonly used in pharmacologic stress testing. It produces hyperemia quickly and maintains it for a duration that is useful for radionuclide myocardial perfusion imaging. The selective nature of the drug makes it preferable to other stress agents such as adenosine, which are less selective and therefore cause more side-effects.

Chemical Structure

Regadenoson (free base)
Regadenoson (free base)
CAS#313348-27-5 (free)

Theoretical Analysis

MedKoo Cat#: 318655

Name: Regadenoson (free base)

CAS#: 313348-27-5 (free)

Chemical Formula: C15H18N8O5

Exact Mass: 390.1400

Molecular Weight: 390.35

Elemental Analysis: C, 46.15; H, 4.65; N, 28.71; O, 20.49

Price and Availability

Size Price Availability Quantity
5mg USD 290.00
10mg USD 490.00
25mg USD 990.00
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Related CAS #
313348-27-5 (free) 875148-45-1 (hydrate)
Synonym
Regadenoson; CVT-3146; CVT 3146; CVT3146; Lexiscan.
IUPAC/Chemical Name
1-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-N-methylpyrazole-4-carboxamide
InChi Key
LZPZPHGJDAGEJZ-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CNC(=O)C1=CN(N=C1)C2=NC3=C(C(=N2)N)N=CN3C4C(C(C(O4)CO)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Regadenoson is a selective, short-acting adenosine A2A receptor agonist (Ki = 1.1 nM for pig striatum A2A receptor). It increases coronary blood flow 3.4- to 3.8-fold with a half-time to reversal of 1.9-2.6 minutes in open-chest anesthetized pigs. Regadenoson is used to induce hyperemia, particularly in the context of myocardial perfusion imaging. It has also been found to increase the delivery of compounds to the central nervous system through the blood-brain barrier in animals.
In vitro activity:
Hemodialysis enhances the clearance of regadenoson independent of hemodialyzer permeability and blood/dialysate flow rate. This clearance is modest relative to total body clearance and is unlikely to produce a clinically significant outcome. Reference: J Nucl Cardiol. 2018 Feb;25(1):234-239. https://pubmed.ncbi.nlm.nih.gov/27632986/
In vivo activity:
Results from this study indicate that low-affinity A2A receptor agonists, one being regadenoson, can produce a response that is of equivalent magnitude but more rapid in termination than a high-affinity agonist. Therefore, regadenoson may prove to be superior to high-affinity agonists as coronary vasodilators during myocardial imaging with radionuclide agents. Reference: J Pharmacol Exp Ther. 2001 Jul;298(1):209-18. https://pubmed.ncbi.nlm.nih.gov/11408544/
Solvent mg/mL mM
Solubility
DMF 10.0 25.62
DMSO 14.0 35.87
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 390.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Gharibian KN, Murthy VL, Mueller BA. Influence of hemodialysis on regadenoson clearance in an in vitro hemodialysis model. J Nucl Cardiol. 2018 Feb;25(1):234-239. doi: 10.1007/s12350-016-0667-0. Epub 2016 Sep 15. PMID: 27632986. 2. Pak RW, Kang J, Valentine H, Loew LM, Thorek DLJ, Boctor EM, Wong DF, Kang JU. Voltage-sensitive dye delivery through the blood brain barrier using adenosine receptor agonist regadenoson. Biomed Opt Express. 2018 Jul 30;9(8):3915-3922. doi: 10.1364/BOE.9.003915. PMID: 30338164; PMCID: PMC6191611. 3. Gao Z, Li Z, Baker SP, Lasley RD, Meyer S, Elzein E, Palle V, Zablocki JA, Blackburn B, Belardinelli L. Novel short-acting A2A adenosine receptor agonists for coronary vasodilation: inverse relationship between affinity and duration of action of A2A agonists. J Pharmacol Exp Ther. 2001 Jul;298(1):209-18. PMID: 11408544.
In vitro protocol:
1. Gharibian KN, Murthy VL, Mueller BA. Influence of hemodialysis on regadenoson clearance in an in vitro hemodialysis model. J Nucl Cardiol. 2018 Feb;25(1):234-239. doi: 10.1007/s12350-016-0667-0. Epub 2016 Sep 15. PMID: 27632986.
In vivo protocol:
1. Pak RW, Kang J, Valentine H, Loew LM, Thorek DLJ, Boctor EM, Wong DF, Kang JU. Voltage-sensitive dye delivery through the blood brain barrier using adenosine receptor agonist regadenoson. Biomed Opt Express. 2018 Jul 30;9(8):3915-3922. doi: 10.1364/BOE.9.003915. PMID: 30338164; PMCID: PMC6191611. 2. Gao Z, Li Z, Baker SP, Lasley RD, Meyer S, Elzein E, Palle V, Zablocki JA, Blackburn B, Belardinelli L. Novel short-acting A2A adenosine receptor agonists for coronary vasodilation: inverse relationship between affinity and duration of action of A2A agonists. J Pharmacol Exp Ther. 2001 Jul;298(1):209-18. PMID: 11408544.
1: Strok A, Dolenc Novak M, Guzic Salobir B, Stalc M, Zaletel K. The Effect of Monitored Walking on Extracardiac Intestinal Activity in Myocardial Perfusion Imaging. J Nucl Med Technol. 2024 Sep 17:jnmt.124.267917. doi: 10.2967/jnmt.124.267917. Epub ahead of print. PMID: 39288972. 2: Androulakis E, Georgiopoulos G, Azzu A, Surkova E, Bakula A, Papagkikas P, Briasoulis A, De Silva R, Kellman P, Pennell DJ, Alpendurada F. Reduced response to regadenoson with increased weight: an artificial intelligence based quantitative myocardial perfusion study. J Cardiovasc Magn Reson. 2024 Jul 25:101066. doi: 10.1016/j.jocmr.2024.101066. Epub ahead of print. PMID: 39067701. 3: Wisniewski AM, Chancellor WZ, Young A, Money D, Beller JP, Charlton J, Lunardi N, Yang Z, Laubach VE, Mehaffey JH, Kron IL, Roeser ME. Adenosine 2A Receptor Agonism Improves Survival in Extracorporeal Cardiopulmonary Resuscitation. J Surg Res. 2024 Jul 18;301:404-412. doi: 10.1016/j.jss.2024.06.033. Epub ahead of print. PMID: 39029264. 4: Valenta I, Upadhyaya A, Jain S, Schindler TH. PET/CT Assessment of Flow- Mediated Epicardial Vasodilation in Obesity and Severe Obesity. JACC Adv. 2024 Apr 9;3(5):100936. doi: 10.1016/j.jacadv.2024.100936. PMID: 38939628; PMCID: PMC11198679. 5: Hosten B, Goutal S, Leterrier S, Corvo C, Breuil L, Barret O, Specklin S, Truillet C, Tournier N. Brain delivery enabled by transient blood-brain barrier disruption induced by regadenoson: a PET imaging study. Expert Opin Drug Deliv. 2024 May;21(5):797-807. doi: 10.1080/17425247.2024.2369765. Epub 2024 Jun 20. PMID: 38881261. 6: Chen H, Xing G, Xu W, Chen Y, Xia L, Huang H, Huang J, Hong Q, Luo T, Wang H, Wu Q. The adenosine A2A receptor in human sperm: its role in sperm motility and association with in vitro fertilization outcomes. Front Endocrinol (Lausanne). 2024 May 30;15:1410370. doi: 10.3389/fendo.2024.1410370. PMID: 38872963; PMCID: PMC11169588. 7: Lin KS, Kurnick A, Goel R, Gorbut I, Friedman A, Schrem E, McFarlane SI, Bukharovich I. Myocardial Bridging of Mid-left Anterior Descending Artery (LAD) Presenting As Transient Left Bundle Branch Block During Nuclear Stress Test. Cureus. 2024 Feb 21;16(2):e54654. doi: 10.7759/cureus.54654. PMID: 38523980; PMCID: PMC10959828. 8: Lim P, Agarwal V, Patel KK. How to assess nonresponsiveness to vasodilator stress. J Nucl Cardiol. 2024 Jun;36:101850. doi: 10.1016/j.nuclcard.2024.101850. Epub 2024 Mar 20. PMID: 38518887; PMCID: PMC11180564. 9: Moutzoukis G, Lorenz MK, Schroeder T, Schulte-Steinberg B, Chow K, Kellman P, Bekeredjian R, Schmid N, Mahrholdt H, Seitz A. Systematic underestimation of myocardial perfusion reserve by regadenoson stress perfusion CMR-when haste makes waste. Clin Res Cardiol. 2024 Mar 11. doi: 10.1007/s00392-024-02405-6. Epub ahead of print. PMID: 38466348. 10: Kattapuram N, Shadman S, Morgan EE, Benton C, Awojoodu S, Kim DY, Ramos J, Barac A, Bandettini WP, Kellman P, Weissman G, Carlsson M. Timing of Regadenoson-induced Peak Hyperemia and the Effects on Coronary Flow Reserve. medRxiv [Preprint]. 2024 Jan 16:2024.01.15.23300449. doi: 10.1101/2024.01.15.23300449. PMID: 38410488; PMCID: PMC10896412. 11: Kuronuma K, Miller RJH, Wei CC, Singh A, Lemley MH, Van Kriekinge SD, Kavanagh PB, Gransar H, Han D, Hayes SW, Thomson L, Dey D, Friedman JD, Berman DS, Slomka PJ. Downward myocardial creep during stress PET imaging is inversely associated with mortality. Eur J Nucl Med Mol Imaging. 2024 May;51(6):1622-1631. doi: 10.1007/s00259-024-06611-2. Epub 2024 Jan 23. PMID: 38253908; PMCID: PMC11042981. 12: Park CS, Nadeem A. Advanced Heart Block and Asystole After Regadenoson Infusion: When Cautionary Tales Become Reality. Cureus. 2023 Dec 19;15(12):e50787. doi: 10.7759/cureus.50787. PMID: 38239541; PMCID: PMC10795854. 13: Salgado-Garcia C, Moreno-Ballesteros A, Guardia-Jimena P, Sanchez-de-Mora E, Rebollo-Aguirre AC, Ramirez-Navarro A, Santos-Bueno A, Jimenez-Heffernan A. Role of the clinical radiopharmacist in patient safety during myocardial perfusion imaging with vasodilator stress agents. Rev Esp Med Nucl Imagen Mol (Engl Ed). 2024 Mar-Apr;43(2):84-90. doi: 10.1016/j.remnie.2023.12.005. Epub 2024 Jan 4. PMID: 38184070. 14: Nagy FT, Olajos D, Vattay B, Borzsák S, Boussoussou M, Deák M, Vecsey-Nagy M, Sipos B, Jermendy ÁL, Tóth GG, Nemes B, Merkely B, Szili-Török T, Ruzsa Z, Szilveszter B. Dynamic Perfusion Computed Tomography for the Assessment of Concomitant Coronary Artery Disease in Patients with a History of Percutaneous Transluminal Angioplasty for Chronic Limb-Threatening Ischemia-A Pilot Study. J Cardiovasc Dev Dis. 2023 Oct 25;10(11):443. doi: 10.3390/jcdd10110443. PMID: 37998501; PMCID: PMC10671941. 15: Arai AE, Schulz-Menger J, Shah DJ, Han Y, Bandettini WP, Abraham A, Woodard PK, Selvanayagam JB, Hamilton-Craig C, Tan RS, Carr J, Teo L, Kramer CM, Wintersperger BJ, Harisinghani MG, Flamm SD, Friedrich MG, Klem I, Raman SV, Haverstock D, Liu Z, Brueggenwerth G, Santiuste M, Berman DS, Pennell DJ. Stress Perfusion Cardiac Magnetic Resonance vs SPECT Imaging for Detection of Coronary Artery Disease. J Am Coll Cardiol. 2023 Nov 7;82(19):1828-1838. doi: 10.1016/j.jacc.2023.08.046. PMID: 37914512. 16: Moreno-Caballero M, Moratalla-Aranda E, Villena-García AC. Ventricular tachycardia in myocardial perfusion with regadenoson. Rev Esp Cardiol (Engl Ed). 2024 Feb;77(2):186. English, Spanish. doi: 10.1016/j.rec.2023.07.010. Epub 2023 Oct 12. PMID: 37838183. 17: Weiner J, Heinisch C, Oeri S, Kujawski T, Szucs-Farkas Z, Zbinden R, Guensch DP, Fischer K. Focal and diffuse myocardial fibrosis both contribute to regional hypoperfusion assessed by post-processing quantitative-perfusion MRI techniques. Front Cardiovasc Med. 2023 Sep 19;10:1260156. doi: 10.3389/fcvm.2023.1260156. PMID: 37795480; PMCID: PMC10546174. 18: Jacobson KA, Suresh RR, Oliva P. A2A adenosine receptor agonists, antagonists, inverse agonists and partial agonists. Int Rev Neurobiol. 2023;170:1-27. doi: 10.1016/bs.irn.2023.08.001. Epub 2023 Aug 25. PMID: 37741687; PMCID: PMC10775762. 19: Parizher G, Dugan E, Jaber WA. What is this image? 2023 image 2 results: In vivo demonstration of regadenoson-induced severe ischemia on PET myocardial perfusion imaging in a patient with hypertrophic obstructive cardiomyopathy and nonobstructive coronary artery disease. J Nucl Cardiol. 2023 Oct;30(5):1757-1760. doi: 10.1007/s12350-023-03366-5. PMID: 37603191. 20: Patel JJ, Alzahrani T. Myocardial Perfusion Scan. 2023 Aug 14. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2024 Jan–. PMID: 30969594.