| Identification | More | [Name]
Sodium 4-phenylbutyrate | [CAS]
1716-12-7 | [Synonyms]
4PBA
4PBA SODIUM
4-PHENYLBUTYRATE, NA
4-PHENYLBUTYRIC ACID SODIUM
4-PHENYLBUTYRIC ACID SODIUM SALT
PBNA
PHENYL N-BUTYRATE SODIUM SALT
SODIUM 4-PHENYLBUTYRATE
SODIUM PHENYLBUTYRATE
SPB
Tributyrate
4-PHENYLBUTYRATE | [EINECS(EC#)]
605-612-7 | [Molecular Formula]
C10H11NaO2 | [MDL Number]
MFCD00800247 | [Molecular Weight]
186.18 | [MOL File]
1716-12-7.mol |
| Chemical Properties | Back Directory | [Appearance]
White or yellowish-white powder. | [Melting point ]
224-226°C (dec.) | [storage temp. ]
room temp | [solubility ]
H2O: ≥5mg/mL | [form ]
White to slightly yellow solid | [color ]
white to beige | [Water Solubility ]
water: 10mg/mL | [Stability:]
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 DataBase Reference]
1716-12-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319 | [Precautionary statements ]
P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
36 | [Safety Statements ]
26 | [WGK Germany ]
3 | [RTECS ]
CY9057220 | [HS Code ]
29163990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Description]
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. | [Description]
Sodium 4-phenylbutyrate is a chemical chaperone that has been shown to rescue the trafficking of misfolded proteins.1,2 It also weakly blocks histone deacetylase activity (IC50 = 0.4 mM), which results in cell cycle arrest, differentiation, and/or apoptosis of various tumors.3,4 Formulations containing sodium 4-phenylbutyrate have been used for the treatment of urea cycle disorders.5 | [Chemical Properties]
White or yellowish-white powder. | [Uses]
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. | [Uses]
Sodium 4-Phenylbutyrate is a histone-deacetylase inhibitor. | [Definition]
ChEBI: The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders. | [Brand name]
Buphenyl (Medicis). | [General Description]
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. | [Biological Activity]
Sodium 4-Phenylbutyrate is a histone deacetylase inhibitor that displays anticancer activity. Inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. Also inhibits protein isoprenylation, depletes plasma glutamine, increases production of fetal hemoglobin through transcriptional activation of the γ-globin gene and affects hPPARγ activation. | [Biochem/physiol Actions]
Sodium phenylbutyrate is a histone deacetylase inhibitor. | [Side effects]
Loss of appetite or menstrual changes (delayed/irregular/absent periods) may occur.
Serious side effects including: drowsiness/lightheadedness, easy bruising/bleeding, fast/pounding heartbeat, mental/mood changes, tiredness, signs of metabolic imbalance (such as rapid breathing, muscle twitching/spasms).
| [Synthesis]
0.40 g (2.436 mmol) of 4-phenylbutyric acid was suspended in 30 mL of water, followed by the addition of 0.097 g (2.436 mmol) of sodium hydroxide. After complete dissolution of the acid, the reaction solution was concentrated by rotary evaporator and azeotropically dehydrated twice with toluene. Finally, 0.44 g (96.0% yield) of solid sodium 4-phenylbutyrate was obtained. | [Metabolism]
Sodium phenylbutyrate (4-PBA sodium salt; Sodium 4-phenylbutyrate) is a prodrug approved by the FDA and indicated as adjunctive therapy in urea cycle disorders. 4-PBA is rapidly metabolized to phenylacetate, an active metabolite, that conjugates with glutamine via acetylation to form phenylacetylglutamine, which is finally excreted by kidneys[2]. | [storage]
Desiccate at -20°C | [References]
1) Engelhard et al. (1998), Inhibitory effects of phenylbutyrate on the proliferation, morphology, migration and invasiveness of malignant glioma cells; J. Neuro-Oncol., 37 97
2) Appelskog et al. (2004), Histone deacetylase inhibitor 4-phenylbutyrate suppresses GAPDH mRNA expression in glioma cells; Int. J. Oncol., 24 1419 |
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| Company Name: |
Rushpharm Co.,Ltd. Gold
|
| Telephone: |
025-66042949 15161141411 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList30642/0_EN.htm |
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|