CAS 313348-27-5 Regadenoson (HCID 219024)

Overview

Regadenoson is a purine nucleoside.

Names & identifiers

Preferred name: Regadenoson
IUPAC: 1-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-N-methylpyrazole-4-carboxamide
English name: REGADENOSON
Molecular formula: C15H18N8O5
Molecular weight: 390.35

Names & synonyms

Regadenoson313348-27-5RapiscanCVT-3146CVT 3146Adenosine, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]-(1-(9-(3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-6-aminopurin-2-yl)pyrazol-4-yl)-N-methylcarboxamide1-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-N-methylpyrazole-4-carboxamideAdenosine, 2-(4-((methylamino)carbonyl)-1H-pyrazol-1-yl)-CHEMBL39896951-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)purin-2-yl)-N-methylpyrazole-4-carboxamideRefChem:426699

Show more names

CS-1874RigadsonRigadasonCVT-3146|||LexiscanREGADENOSON，98% minRegadenoson ImpurityRegadenoson(CVT-3146)

690-885-52XLN4Y044HADENOSINE, 2-(4-((METHYLAMINO)CARBONYL)-1H-PYRAZOL-1-YL)-, MONOHYDRATECVT3146Regadenoson monohydrateLexiscanRegadenoson anhydrous2-[4-[(Methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine

Database identifiers

CAS: 313348-27-5
PubChem CID: 219024
DTXSID: DTXSID4057712
ChEMBL: CHEMBL317052、CHEMBL3989695
ChEBI: CHEBI:135613
UNII: 7AXV542LZ4
EC Number: 690-885-5
Nikkaji: J1.806.399I

Properties

Computed structural properties

XLogP: -1.5
Topological polar surface area: 186 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 10
Rotatable bonds: 4
Heavy atoms: 28
Formal charge: 0
Complexity: 587

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 4 items

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

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point: 158 · 158-160°C
Density: 1.98 · 1.98±0.1 g/cm3(Predicted)
storage temp.: 2 · Keep in dark place,Sealed in dry,2-8°C
solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
form: Solid
pka: 13.07 · 13.07±0.70(Predicted)
color: Off-White to Pale Brown
InChIKey: LZPZPHGJDAGEJZ-AKAIJSEGSA-N
SMILES: OC[C@H]1O[C@@H](N2C3C(=C(N=C(N4C=C(C(NC)=O)C=N4)N=3)N)N=C2)[C@H](O)[C@@H]1O
CAS DataBase Reference: 313348 · 313348-27-5
FDA UNII: 7 AXV542LZ4 · 7AXV542LZ4
NCI Drug Dictionary: regadenoson
ATC code: 1 EB21 · C01EB21
UNSPSC Code: 12352211 · 12352211
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 300 · H300-H330-H310
Precautionary statements: 260 · P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
WGK Germany: 3 · WGK 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H300 (66.7%): Fatal if swallowed [Danger Acute toxicity, oral]

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, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

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

Hazard information

Hazard Classes and CategoriesAcute Tox. 1 (66.7%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Regadenoson

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk: WGK 3
Signal word: Danger
Symbol(GHS): GHS06
Storage Class: 11 - Combustible Solids
Hazard statements: H300-H330-H310
Precautionary statements: P260-P271-P284-P304+P340-P310-P320-P403+P233-P405-P501-P262-P264-P270-P280-P302+P350-P310-P322-P361-P363-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501

Chemistry & industry

Pharmacology

ATC Code · 3 items

C01EB21

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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

Biological Half-LifeInitial phase: 2-4 minutes; Intermediate phase: 30 minutes (this phase coincides with a loss of the pharmacodynamic effect); Terminal phase: 2 hours

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

FDA Pharmacological Classification · 6 items

2XLN4Y044H

REGADENOSON

Established Pharmacologic Class [EPC] - Adenosine Receptor Agonist

Mechanisms of Action [MoA] - Adenosine Receptor Agonists

Regadenoson is an Adenosine Receptor Agonist. The mechanism of action of regadenoson is as an Adenosine Receptor Agonist.

7AXV542LZ4

Applications · 4 items

DescriptionLexiscan ™(regadenoson) is an injectable adenosine A2A receptor agonist for use as a pharmacologic stress agent in myocardial perfusion imaging (MPI) studies in patients unable to undergo adequate exercise induced stress. Regadenoson is the first adenosine A2A receptor agonist shown to be safe and effective as a pharmacologic stress agent in MPI studies. It is delivered as a rapid bolus (approximately 10 seconds) with no dose adjustment required for body weight. The product was developed under a license and collaboration agreement between CV Therapeutics and Astellas, and was launched by Astellas in June of 2008.

UsesA selective A2A adenosine receptor agonist in myocardial imaging

UsesRegadenoson 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 (increased blood flow), 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.

UsesRegadenoson is a selective and potent A2A adenosine receptor agonist (1). The adenosine A2A receptor is a G-protein-coupled receptor and a key therapeutic target for oncologic, inflammatory, Parkinson''s and cardiovascular diseases (2). In rodent studies, it has been shown that co-administration of Regadenoson with Temozolomide (T017775) can increase Temozolomide concentration in the brain (3).