Sodium Phenylbutyrate
SODIUM PHENYLBUTYRATE · PBNA · 4PBA · Tributyrate · 4-PHENYLBUTYRATE · Ammonaps · Nsc657802 · 4PBA SODIUM
Identifikatoren & physikalische Daten
| CAS No. | 1716-12-7 |
|---|---|
| Summenformel | C10H11NaO2 |
| Durchschnittliche Molmasse | 186,18 g/mol |
| Monoisotopische Masse | 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 |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 40,1 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 142 |
| Human Drugs | Breast FeedingLactationMilk, HumanUrea Cycle DisordersFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Schmelzpunkt | 224-226°C (dec.) |
| Lagerbedingungen | room temp |
| Löslichkeit | H2O: ≥5mg/mLwater: 10mg/mL |
| Aggregatzustand | White to slightly yellow solid |
| Farbe | white to beige |
| Stabilität | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months. |
| 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 Datenbank | 1716-12-7(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29163990 |
| RTECS-Nr. | CY9057220 |
| R-Sätze (R) | 36 |
| Gefahrensymbole | Xi |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.