基本情報
- CAS
2627-69-2- 標準SMILES
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N- InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N- 分子式
- C9H14N4O5
- 平均分子量
- 258.23 g/mol
- 単同位体質量
- 258.09641955
概要
Acadesine is a 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects. It has a role as an antineoplastic agent and a platelet aggregation inhibitor. It is an aminoimidazole, a 1-ribosylimidazolecarboxamide and a nucleoside analogue.
名称と識別子
- 優先名称
- Acadesine
- IUPAC
- 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
- 現地名
- アカデシン
- 英語名
- AICAR
- 分子式
- C9H14N4O5
- 分子量
- 258.23
名称と別名
ACADESINE2627-69-2AICA-ribosideArasineAICA ribosideAcadesinaAIC-RibosideAcadesinumGP-1-110ProtaraDTXSID50460155-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide
名称をさらに表示
4-アミノ-3-(β-D-リボフラノシル)-3H-イミダゾール-5-カルボアミド1-デオキシ-1-(5-アミノ-4-カルバモイル-1H-イミダゾール-1-イル)-β-D-リボフラノース5-アミノ-1-(β-D-リボフラノシル)-1H-イミダゾール-4-カルボアミドアカデシン1-デオキシ-1-[(4-カルバモイル-5-アミノ-1H-イミダゾール)-1-イル]-β-D-リボフラノースAICA-リボシドアミノイミダゾールカルボキサミドリボフラノシド5-アミノイミダゾール-4-カルボキシアミドリボヌクレオシドAICA-β-D-リボシド5-アミノ-1-β-D-リボフラノシルイミダゾール-4-カルボキサミド5-アミノ-1-β-D-リボフラノシル-1H-イミダゾール-4-カルボアミド1-β-D-リボフラノシル-5-アミノ-1H-イミダゾール-4-カルボアミド1-(β-D-リボフラノシル)-5-アミノ-1H-イミダゾール-4-カルボアミド5-アミノイミダゾール-4-カルボキサミド-1-β-D-リボフラノシドアラシン5-アミノイミダゾール-4-カルボキサミド1-β-D-リボフラノシド5-アミノ-1-(β-D-リボフラノシル)-1H-イミダゾール-4-カルボキサミド5-アミノ-1-Β-D-リボフラノシル-1H-イミダゾール-4-カルボキサミド
物性
構造計算による物性
- XLogP
- -2.2
- 極性表面積
- 157 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 7
- 回転可能結合数
- 3
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 330
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section
170.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
152 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
153.55 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
153 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 214 · 214-215 °C
- 沸点
- 726.3 · 726.3±60.0 °C(Predicted)
- 比重(密度)
- 2.06 · 2.06±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 2 O: · H2O: >10 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 13.27 · 13.27±0.70(Predicted)
- 色
- タン
- 由来生物
- rabbit
- 水溶解度
- 2 mg/mlでDMSOに可溶。水またはエタノールに1mg/ml未満で可溶 · 2mg/mlでDMSOに可溶。水またはエタノールに1mg/ml未満で可溶
- Merck
- 14 · 14,16
- Specific Activity
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 4.4% (2 of 45) of reports.
Warning
H315 (93.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 7 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 CategoriesSkin Irrit. 2 (93.3%)
安全データ
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29349990
- risk_code
- 36/37/38-61
- 化審法
- (9)-119
- hazard_code
- Xi,T
- safety_code
- 26-36-45-53
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein BindingNegligible (approximately 1%)
Pharmacodynamics
Acadesine has been shown to induce cell death apoptosis selectively in B-cells taken from healthy subjects and patients with B-CLL, with little effect on T-cells. As T-cells have an important role in fighting infection, it is anticipated that patients treated with acadesine will have a reduced risk of serious infections compared to those on current chemotherapies.
Mechanism of Action
The mechanism by which acadesine selectively kills B-cells is not yet fully elucidated. The action of acadesine does not require the tumour suppressor protein p53 like other treatments. This is important, as p53 is often missing or defective in cancerous B-cells. Studies have shown acadesine activates AMPK and induces apoptosis in B-cell chronic lymphocytic leukemia cells but not in T lymphocytes.
Biological Half-Life1 week
用途と製造
General Manufacturing Information1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-: ACTIVE
応用分野
使用AICAR is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) hav e been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.
一般的な説明Adenosine monophosphateprotein kinase (AMPK) activator 5-aminoimidazole-4-carboxamideribonucleotide(AICAR)modulates cellular energy. It regulates lipid and glucose metabolism, pro-inflammatory responses,cytokine production,cell proliferation and apoptosis. AICAR improves ischemia or reperfusion injury and kidney fibrosis in rats. It provides protection against acute tubular necrosis.
関連反応
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化合物ノート
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