Regadenoson (HCID 219024)

概要

Regadenoson is a purine nucleoside.

名称と識別子

優先名称: 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
現地名: レガデノソン
英語名: REGADENOSON
分子式: C15H18N8O5
分子量: 390.35

名称と別名

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

名称をさらに表示

レガデノソン1-{6-アミノ-9-[(2R,3R,4S,5R)-3,4-ジヒドロキシ-5-(ヒドロキシメチル)オキソラン-2-イル]-9H-プリン-2-イル}-N-メチル-1H-ピラゾール-4-カルボキサミド2-[4-(メチルカルバモイル)-1H-ピラゾール-1-イル]アデノシンN-メチル-1-(アデノシン-2-イル)-1H-ピラゾール-4-カルボアミド2-[4-(メチルアミノカルボニル)-1H-ピラゾール-1-イル]アデノシン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

データベース識別子

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

物性

構造計算による物性

XLogP: -1.5
極性表面積: 186 Å²
水素結合供与体数: 5
水素結合受容体数: 10
回転可能結合数: 4
重原子数: 28
形式電荷: 0
複雑度: 587

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 4 件

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

物理化学的性質

融点: 158 · 158-160°C
比重(密度): 1.98 · 1.98±0.1 g/cm3(Predicted)
貯蔵温度: 2 · Keep in dark place,Sealed in dry,2-8°C
溶解性: DMSO（わずかに）、メタノール（わずかに、超音波処理）
外見: 個体
酸解離定数(Pka): 13.07 · 13.07±0.70(Predicted)
色: オフホワイトからペールブラウン
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 データベース: 313348 · 313348-27-5

化学的性質

化学的特性Off-White Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 1 (66.7%)

毒性情報

Drug Induced Liver Injury · 6 件

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

安全データ

wgk: WGK 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 3 件

C01EB21

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 件

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 件

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 件

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

応用分野 · 2 件

説明Lexiscan ™(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.

使用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 (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.