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Sodium 4-phenylbutyrate

CAS No.
1716-12-7
Chemical Name:
Sodium 4-phenylbutyrate
Synonyms
SODIUM PHENYLBUTYRATE;PBNA;4PBA;Tributyrate;Ammonaps;Nsc657802;4PBA SODIUM;4-PHENYLBUTYRATE;4-PHENYLBUTYRATE, NA;Sodium 4-Phenylbutyr
CBNumber:
CB5213148
Molecular Formula:
C10H13NaO2
Molecular Weight:
188.2
MDL Number:
MFCD00800247
MOL File:
1716-12-7.mol
MSDS File:
SDS
Last updated:2024-01-18 17:02:57

Sodium 4-phenylbutyrate 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)
FDA UNII NT6K61736T
NCI Drug Dictionary sodium phenylbutyrate
ATC code A16AX03

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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
NFPA 704
0
2 0

Sodium 4-phenylbutyrate price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR3237 Sodium Phenylbutyrate pharmaceutical secondary standard, certified reference material 1716-12-7 500MG $230 2024-03-01 Buy
Sigma-Aldrich 567616 Sodium 4-Phenylbutyrate 1716-12-7 100mg $82.8 2024-03-01 Buy
Sigma-Aldrich 1614512 Sodium phenylbutyrate United States Pharmacopeia (USP) Reference Standard 1716-12-7 200mg $436 2024-03-01 Buy
TCI Chemical O0511 Sodium 4-Phenylbutyrate 1716-12-7 1G $94 2024-03-01 Buy
TCI Chemical O0511 Sodium 4-Phenylbutyrate 1716-12-7 5G $321 2024-03-01 Buy
Product number Packaging Price Buy
PHR3237 500MG $230 Buy
567616 100mg $82.8 Buy
1614512 200mg $436 Buy
O0511 1G $94 Buy
O0511 5G $321 Buy

Sodium 4-phenylbutyrate Chemical Properties,Uses,Production

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

Sodium 4-Phenylbutyrate is a histone-deacetylase inhibitor.

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 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).

1821-12-1
1716-12-7
Synthesis of Sodium 4-phenylbutyrate from 4-Phenylbutyric acid

Sodium 4-phenylbutyrate Preparation Products And Raw materials

Global( 280)Suppliers
Supplier Tel Email Country ProdList Advantage
Jiangsu shring Biopharma Co., Ltd.
+8613372282299 sales@shringchem.com China 3545 58
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+undefined13585446801 sales@uniringchem.com China 68 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886 info@dakenam.com China 14770 58
Henan Tianfu Chemical Co.,Ltd.
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Hangzhou FandaChem Co.,Ltd.
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Changzhou Ditong Chemical Co.,Ltd
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View Lastest Price from Sodium 4-phenylbutyrate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
 Sodium 4-phenylbutyrate  pictures 2023-06-15 Sodium 4-phenylbutyrate
1716-12-7
US $705.00 / KG 1KG 98% 1-10mt Baoji Guokang Bio-Technology Co., Ltd.
Sodium 4-phenylbutyrate pictures 2023-03-29 Sodium 4-phenylbutyrate
1716-12-7
US $80.00 / kg 1kg 99% 20 tons Hebei Duling International Trade Co. LTD
Sodium 4-phenylbutyrate pictures 2023-03-29 Sodium 4-phenylbutyrate
1716-12-7
US $100.00 / kg 1kg 99% 20 tons Hebei Duling International Trade Co. LTD

Sodium 4-phenylbutyrate Spectrum

SODIUM 4-PHENYLBUTYRATE PHENYL N-BUTYRATE SODIUM SALT 4-PHENYLBUTYRATE, NA 4-PHENYLBUTYRIC ACID SODIUM 4-PHENYLBUTYRIC ACID SODIUM SALT 4PBA SODIUM Nsc657802 SodiuM 4-Phenylbutanoate 4-PHENYLBUTYRATE Benzenebutanoic acid,sodiuM salt (1:1) Sodium Phenylbutyrate (200 mg) Sodium phenylbutyrate, >=98% Sodium phenylbutyrate, 98%, a histone deacetylase inhibitor Sodium 4-Phenylbutyrate - CAS 1716-12-7 - Calbiochem Benzenebutyric acid sodium Sodium phenylbutyrate CRS Sodium 4-phenylbutyrate USP/EP/BP Sodium 4-Phenylbutyr Ammonaps Sodium Phenylbutyrate (4-PBA sodium) Sodium Phenylbutyrate (1614512) SODIUM PHENYLBUTYRATE PBNA 4PBA Tributyrate 1716-12-7 716-12-7 C10H11O2Na C10H11NaO2 VASOTEC 1716-12-7