페닐부틸산나트륨
페닐부틸산나트륨 · SODIUM PHENYLBUTYRATE · PBNA · 4PBA · Tributyrate · 4-PHENYLBUTYRATE · Ammonaps · Nsc657802
식별자 및 물리적 특성
| CAS No. | 1716-12-7 |
|---|---|
| 분자식 | C10H11NaO2 |
| 평균 분자량 | 186.18 g/mol |
| 단동위원소 질량 | 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 |
| 현지명 | 페닐부틸산나트륨 |
화학 및 물리적 성질
| 극성 표면적 | 40.1 |
|---|---|
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 4 |
| 무거운 원자 수 | 13 |
| 형식 전하 | 0 |
| 복잡도 | 142 |
| Human Drugs | Breast FeedingLactationMilk, HumanUrea Cycle DisordersFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| 녹는점 | 224-226°C (dec.) |
| 저장 조건 | room temp |
| 용해도 | H2O: ≥5mg/mL |
| 물리적 상태 | 흰색 ~ 약간 노란색의 고체 |
| 색상 | 흰색에서 베이지색 |
| 용해도 | water: 10mg/mL |
| 안정성 | 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 증류수에 용해된 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다. |
| 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] |
화학적 성질
White or yellowish-white powder.
안전 및 규제
| GHS 분류 | 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 |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | CY9057220 |
| 관세 코드 | 29163990 |
| 위험 문구(R) | 36 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
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.
일반 설명
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.