4-フェニル酪酸ナトリウム
4-フェニル酪酸ナトリウム · フェニル酪酸ナトリウム · フェニル酪酸ナトリウム (JAN) · ブフェニール · 4-フェニルブタン酸ナトリウム · ベンゼンブタン酸ナトリウム · ナトリウム 4-フェニルブタノアート · SODIUM PHENYLBUTYRATE
識別子と物理属性
| CAS No. | 1716-12-7 |
|---|---|
| 分子式 | C10H11NaO2 |
| 平均分子量 | 186.18 g/mol |
| 単同位体質量 | 186.06567387 g/mol |
| SMILES | O=C([O-])CCCc1ccccc1.[Na+] |
| InChIKey | VPZRWNZGLKXFOE-UHFFFAOYSA-M |
| PubChem CID | 5258 |
| ChEMBL | CHEMBL1333672 |
| ChEBI | CHEBI:75316 |
| EC No. | 605-612-7 |
| DTXSID | DTXSID7040948 |
| 現地名 | 4-フェニル酪酸ナトリウム |
化学・物理的性質
| 極性表面積 | 40.1 |
|---|---|
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 4 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 142 |
| Human Drugs | Breast FeedingLactationMilk, HumanUrea Cycle DisordersFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| 融点 | 224-226°C (dec.) |
| 貯蔵条件 | room temp |
| 溶解度 | H2O: ≥5mg/mLwater: 10mg/mL |
| 外観・状態 | 白色～わずかに黄色の固体 |
| 色 | 白からベージュ |
| 安定性 | DMSO 溶液または蒸留水で -20°C で最大 3 か月間保存できます。 |
| InChI | InChI=1S/C10H12O2.Na.H/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12) |
| InChIKey | OBKXEAXTFZPCHS-UHFFFAOYSA-N |
| SMILES | C(C1C=CC=CC=1)CCC(=O)O.[NaH] |
| CAS データベース | 1716-12-7(CAS DataBase Reference) |
化学的特性
White or yellowish-white powder.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 2.3% (1 of 44) of reports.WarningH319 (93.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Eye Irrit. 2 (93.2%) |
| Hepatotoxicity | While the urea cycle disorders are caused by deficiencies of hepatic enzymes responsible for the elimination of nitrogen, patients generally present with hyperammonemia without other features or biochemical evidence of hepatic injury. Thus, serum aminotransferase, alkaline phosphatase and bilirubin levels are generally normal or only mildly elevated. Newborns presenting with hyperammonemia may have hepatomegaly but other, non-urea cycle, liver function is normal as is hepatic histology. Phenylbutyrate can help to lower ammonia levels acutely and manage to keep them in the normal or near normal range, but generally does not affect other liver functions. In open label studies, a small proportion of patients (particularly with ornithine transcarbamylase [OTC] deficiency) have had ALT or AST elevations, but these have generally been attributed to the underlying condition or its complications. Phenylbutyrate has not been linked to instances of clinically apparent liver injury with jaundice. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Sodium phenylbutyrateAmbiguous-DILI-concern4Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | CY9057220 |
| 税関コード | 29163990 |
| 危険文句（R） | 36 |
| 危険表示 | Xi |
| 安全措置（S） | 26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
Sodium 4-phenylbutyrate (4-PBA sodium) is an inhibitor of HDAC and endoplasmic reticulum (ER) stress, used in cancer and infection research.Sodium phenylbutyrate stimulates urinary nitrogen excretion. It is a prodrug, which undergoes β-oxidation to phenylacetate. Sodium phenylbutyrate is used to treat urea cycle disorder. It might be associated with menstrual dysfunction, amenorrhea and painful mucositis of the esophagus and stomach.Sodium phenylbutyrate has been used as an endoplasmic reticulum (ER) stress inhibitor to study the role of ER stress in the expression of betatrophin.
使用
ACE inhibitor, antihypertensive, Inhibitor of histone deacetylase (HDAC). Anti-neoplastic agent and transcriptional regulator. Also acts as an inducer of tumor cytostasis and differentiation.Sodium 4-phenylbutyrate is a chemical chaperone that has been shown to rescue the trafficking of misfolded proteins.It also weakly blocks histone deacetylase activity (IC50 = 0.4 mM), which results in cell cycle arrest, differentiation, and/or apoptosis of various tumors.Formulations containing sodium 4-phenylbutyrate have been used for the treatment of urea cycle disorders.
一般的な説明
An antineoplastic agent that demonstrates potent differentiating capacity in multiple hematopoietic and solid tumor cell lines. Acts as an inducer of tumor cytostasis and differentiation as well as of peroxisomal proliferation. A more effective inhibitor of histone deacetylase and inducer of histone acetylation than its structural analogs including 2- and 3-phenylbutyrate. Acts as a transcriptional regulator and improve the targeting of δF508-CFTR (cystic fibrosis transmembrane regulator) for ubiquitination and degradation by reducing the expression of HSC70 in epithelial cells. Also, reported to increase fetal hemoglobin production in vitro and in vivo.