Sodium 4-phenylbutyrate

Bezeichnung:Sodium 4-phenylbutyrate

CAS-Nr1716-12-7

Englisch Name:Sodium 4-phenylbutyrate

CBNumberCB5213148

SummenformelC10H13NaO2

Molgewicht188.2

MOL-Datei1716-12-7.mol

Sodium 4-phenylbutyrate physikalisch-chemischer Eigenschaften

Schmelzpunkt	224-226°C (dec.)
storage temp.	room temp
Löslichkeit	H2O: ≥5mg/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

Kennzeichnung gefährlicher	Xi
R-Sätze:	36
S-Sätze:	26
WGK Germany	3
RTECS-Nr.	CY9057220
HS Code	29163990

Gefahreninformationscode (GHS)

Sodium 4-phenylbutyrate Chemische Eigenschaften,Einsatz,Produktion Methoden

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.
Beschreibung
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.
Chemische Eigenschaften
White or yellowish-white powder.
Verwenden
Sodium 4-Phenylbutyrate is a histone-deacetylase inhibitor.
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.
Verwenden
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.
Trademarks
Buphenyl (Medicis).
Allgemeine Beschreibung
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.
Biologische Aktivität
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.
Nebenwirkungen
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).
Stoffwechsel
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].
Lager
Desiccate at -20°C
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

Sodium 4-phenylbutyrate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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