Regadenoson (HCID 219024)

개요

Regadenoson is a purine nucleoside.

이름 및 식별자

우선 이름: 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
현지명: 레가데노손
영어명: REGADENOSON
분자식: C15H18N8O5
분자량: 390.35

이름 및 동의어

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

이름 더 보기

레가데노손CS-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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -1.5
극성 표면적: 186 Å²
수소 결합 공여자 수: 5
수소 결합 수용자 수: 10
회전 가능 결합 수: 4
무거운 원자 수: 28
형식 전하: 0
복잡도: 587

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 4건

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

물리화학적 성질

녹는점: 158 · 158-160°C
밀도: 1.98 · 1.98±0.1 g/cm3(Predicted)
저장 조건: 2 · Keep in dark place,Sealed in dry,2-8°C
용해도: DMSO(약간 용해됨), 메탄올(약간 용해됨, 초음파처리)
물리적 상태: 고체
산도 계수 (pKa): 13.07 · 13.07±0.70(Predicted)
색상: 미색부터 옅은 갈색까지
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

화학적 성질

Off-White Solid

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 1 (66.7%)

독성 정보

Drug Induced Liver Injury · 6건

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

안전 데이터

wgk: WGK 3
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 3건

C01EB21

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1건

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 · 1건

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 · 6건

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

응용 분야 · 2건

개요Lexiscan ™(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.

용도Regadenoson 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.