Sodium 4-phenylbutyrate Chemical Properties

Melting point:

224-226°C (dec.)

storage temp. 

room temp

solubility 

H2O: ≥5mg/mL

form 

White to slightly yellow solid

color 

white to beige

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 Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

RTECS 

CY9057220

HS Code 

29163990

Sodium 4-phenylbutyrate Usage And Synthesis

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. 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.

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.

Uses

Sodium phenylbutyrate has been used as an endoplasmic reticulum (ER) stress inhibitor to study the role of ER stress in the expression of betatrophin.

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).

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.
[2] Salvatore Villani. “Quantification of the Chemical Chaperone 4-Phenylbutyric Acid (4-PBA) in Cell Culture Media via LC-HRMS: Applications in Fields of Neurodegeneration and Cancer.” Pharmaceuticals 16 2 (2023).

Sodium 4-phenylbutyrate(1716-12-7)Related Product Information

• Sodium benzoate
• 3-BENZOYLPROPIONIC ACID
• Hydrocortisone-17-butyrate
• Indole-3-butyric acid
• Butyric Acid
• Sodium sulfate
• Trisodium phosphate
• Sodium chloride
• Sodium chlorite
• Diclofenac sodium
• MCPA SODIUM
• Sodium acetate
• 4-Aminobutyric acid
• Sodium bicarbonate
• 4-Phenylbutyric acid
• Sodium hydroxide
• Sodium Butyrate
• 1-Tetralone