ネララビン

2-(2-Amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

HCID 248862

基本情報

CAS
121032-29-9
標準SMILES
COc1nc(N)nc2c1ncn2C1OC(CO)C(O)C1O
InChIKey
IXOXBSCIXZEQEQ-UHFFFAOYSA-N
分子式
C11H15N5O5
平均分子量
297.27 g/mol

名称と識別子

優先名称
2-(2-Amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
IUPAC
2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
現地名
ネララビン
英語名
Nelarabine
分子式
C11H15N5O5
分子量
297.27

名称と別名

34793-34-5MFCD01723912S12132-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolCHEMBL1513356SCHEMBL13657986SCHEMBL29401939(2R,3R,4R,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolHMS3654B03HMS5079I17(2R,3R,4S,5R)-2-(2-amino-6-methoxy-9H-purin-9-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diolNSC66381
名称をさらに表示
ネララビンネルザラビンネララビン (JAN)アラノンジー2-アミノ-6-メトキシプリンアラビノシド6-メトキシ-9-β-D-アラビノフラノシル-9H-プリン-2-アミン(2R)-2β-(2-アミノ-6-メトキシ-9H-プリン-9-イル)-5β-(ヒドロキシメチル)テトラヒドロフラン-3β,4α-ジオール(2R,3S,4S,5R)-2-(2-アミノ-6-メトキシ-9H-プリン-9-イル)-5-(ヒドロキシメチル)オキソラン-3,4-ジオール9-(β-D-アラビノフラノシル)-6-メトキシ-9H-プリン-2-アミンMAYArranonNELARABINNelzarabine506u506U78CS-1953GW 506U78NELARABINENelarabine D4
Arranon (TN) (Glaxo Smith Kline)NSC-66381NSC132361NSC-132361SB19492DB-226463AB01273946-012-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

データベース識別子

CAS
121032-29-9、34793-34-5、7803-88-5
PubChem CID
248862
ChEMBL
CHEMBL1513356

物性

構造計算による物性

XLogP
-0.7
極性表面積
149 Ų
水素結合供与体数
4
水素結合受容体数
9
回転可能結合数
3
重原子数
21

物理化学的性質

融点
209 · 209-217°
比旋光度
20 · D20 +55.9° (c = 0.27 in DMF)
沸点
721 · 721.0±70.0 °C(Predicted)
比重(密度)
1.98 · 1.98±0.1 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C(protect from light)
溶解性
DMSO(わずかに)、メタノール(わずかに、加熱)、水(わずかに、超音波処理)

安全と法規制

安全データ

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

化学と産業

応用分野 · 3 件

用途DNA 合成阻害作用を示します。

説明Nelarabine is a new member of the purine nucleoside antimetabolite class of drugs. It was launched as an intravenous infusion for treating relapsed or refractory T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL) after at least two prior chemotherapy regimens. Nelarabine is a pro-drug of 9-b-D-arabinofuranosylguanine (ara-G), a deoxyguanosine derivative with a high level of T-cell selective cytotoxicity. Although Ara-G has been known since the 1960s, it has not been used in clinical studies due to its poor solubility. Nelarabine is the O-methyl derivative of ara-G with approximately 10 times greater aqueous solubility. It is demethylated in vivo by adenosine deaminase to produce ara-G, which is subsequently converted to the active 5’-triphosphate, ara-GTP. Accumulation of ara-GTP in leukemic blasts allows for incorporation into DNA, leading to inhibition of DNA synthesis and cell death.

使用A chemotherapy drug used in the treatment of relapsed/refractory T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL).

サプライヤー100 社

北京华美互利生物化工010-56205725 · [email protected]
上海策嵘生物科技有限公司[email protected]
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温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
補足説明 · 1 件

定義ChEBI: Nelarabine is a purine nucleoside in which O-methylguanine is attached to arabinofuranose via a beta-N(9)-glycosidic bond. Inhibits DNA synthesis and causes cell death; a prodrug of 9-beta-D-arabinofuranosylguanine (ara-G). It has a role as an antineoplastic agent, a DNA synthesis inhibitor and a prodrug. It is a purine nucleoside, a beta-D-arabinoside and a monosaccharide derivative. It is functionally related to a guanine and a 9-beta-D-arabinofuranosylguanine.

関連反応

1 件

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