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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 377
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)
- 外見
- 個体
- 酸解離定数(Pka)
- 13.07 · 13.07±0.70(Predicted)
- 色
- 白い
- 水溶解度
- 2 O: · H2O: 5mg/mL, clear (warmed)
- InChI
- InChI=1/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/s3
- InChIKey
- IXOXBSCIXZEQEQ-GCTRTDOSNA-N
- SMILES
- N1(C=NC2C(OC)=NC(N)=NC1=2)[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 |&1:12,13,15,17,r|
- CAS データベース
- 121032 · 121032-29-9(CAS DataBase Reference)
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
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
補足説明
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.
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