Sodium Phenylbutyrate (4-PBA sodium)

Alias:

4-PBA sodium; Sodium 4-phenylbutyrate; Sodium phenylbutyrate; 4-phenylbutyrate (4-PBA); 4-phenylbutyric acid; Buphenyl

Cat No.:V0284 Purity: ≥98%

COA Product Data Instructions for use SDS

Sodium Phenylbutyrate (4-PBA sodium) Chemical Structure CAS No.: 1716-12-7
Product category: HDAC

This product is for research use only, not for human use. We do not sell to patients.

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Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Sodium phenylbutyrate (4-Phenylbutyric acid sodium; 4-PBA sodium), an orphan drug marketed by Ucyclyd Pharma, is a novel and potent histone deacetylase (HDAC) inhibitor used as an as adjunctive therapy for chronic treatment of urea cycle disorders involving deficiencies of argininosuccinic acid synthetase (AS), ornithine transcarbamylase (OTC), or carbamylphosphate synthetase (CPS). Because metabolites of sodium phenylbutyrate offer an alternative pathway to the urea cycle for the excretion of excess nitrogen. It has strong anti-cancer properties as well.

Biological Activity I Assay Protocols (From Reference)

Targets

HDAC

ln Vitro

In vitro activity: Phenylbutyrate is a well-known HDAC inhibitor that has neuroprotective properties in addition to increasing the transcription of several genes. In the substantia nigra, phenylbutyrate significantly reduces the effects of MPTP-induced striatal dopamine depletion and tyrosine hydroxylase-positive neuronal loss.[1] In prostate cancer cells, phenylbutyrate reduces the expression of the pro-angiogenic vascular endothelial growth factor, the pro-angiogenic vascular endothelial growth factor, the prostate progression marker caveolin-1, and the double-strand break repair protein DNA-dependent protein kinase. It is discovered that phenylbutyrate and ionizing radiation work together to cause prostate cancer cells to undergo apoptosis.[2]

ln Vivo

Phenylbutyrate greatly increases survival and improves both the clinical and neuropathological phenotypes in G93A transgenic ALS mice. Administration of phenylbutyrate reduces the expression of cytochrome c and caspase, but ameliorates the histone hypoacetylation seen in G93A mice and induces the expression of nuclear factor-kappaB (NF-kappaB) p50, the phosphorylated inhibitory subunit of NF-kappaB (pIkappaB), and beta cell lymphoma 2 (bcl-2). Phenylbutyrate either directly acetylates NF-kappaB p50 or phosphorylates IkappaB, causing NF-kappaB p50 to be translocated to the nucleus.[3] Phenylbutyrate increases brain histone acetylation and decreases histone methylation levels as determined by immunocytochemistry and Western blots. in a transgenic mousemodel of Huntington's disease (HD). Phenylbutyrate down-regulated caspases linked to apoptotic cell death, increased mRNA for ubiquitin-proteosomal pathway components, and increased caspase 3 immunoreactivity in the striatum.[4]

Cell Assay

In brief, viable cells are seeded at a density of 4 × 10⁴ cells/mL in 60-mm dishes in RPMI 1640 with 10% fetal bovine serum and 0.35% agarose on a base layer of 0.7% agarose. Viable cells are determined by trypan blue dye exclusion. Additions of DMSO, TSA, or PB are made to the upper and lower agarose layers. Colonies are counted after 10–14 days, and assays are run in triplicate at least three times.

Animal Protocol

Mice: 10-week-old female IRC's pathogen-free animal facility is home to C57BL/6J mice. The animals are divided into four groups at random: LPS (n=6), vehicle+Benzenebutyric acid (n=6), vehicle control (n=5), and LPS+Benzenebutyric acid (n=6). For three weeks, mice are given 200 μL of phosphate-buffered saline (PBS) once a week at a dose of 5 mg/kg intraperitoneally. Mice are given a daily intraperitoneal injection of 200 μL PBS (or PBS as a vehicle) containing 240 mg/kg of sodium 4-phenylbutyrate (Benzenebutyric acid) solution, which is made by titrating equimolecular amounts of Benzenebutyric acid and sodium hydroxide to reach pH 7.4. The injections last for three weeks. Mice are killed by asphyxia with CO₂. The right femur is scanned in order to ascertain the long bone's microarchitecture and bone mineral density (BMD). A 6.9 μm effective detector pixel size and a 77–255 mg/cc threshold are used for the scans. A region of 1.6 mm in length, situated 0.1 mm below the distal femur growth plate, is the subject of analysis for trabecular bone.

References

[1]. Neuromolecular Med . 2004;5(3):235-41.

[2]. Neoplasia . 2001 Jul-Aug;3(4):331-8.

[3]. J Neurochem . 2005 Jun;93(5):1087-98.

[4]. J Biol Chem . 2005 Jan 7;280(1):556-63.

[5]. Cell Death Dis . 2021 Oct 29;12(11):1016.

[6]. 2017 Jun 9:8:256.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C10H11O2.NA

Molecular Weight

186.18

Exact Mass

186.07

Elemental Analysis

C, 64.51; H, 5.96; Na, 12.35; O, 17.19

CAS #

1716-12-7

Related CAS #

1716-12-7

Appearance

Solid powder

SMILES

C1=CC=C(C=C1)CCCC(=O)[O-].[Na+]

InChi Key

VPZRWNZGLKXFOE-UHFFFAOYSA-M

InChi Code

InChI=1S/C10H12O2.Na/c11-10(12)8-4-7-9-5-2-1-3-6-9;/h1-3,5-6H,4,7-8H2,(H,11,12);/q;+1/p-1

Chemical Name

sodium;4-phenylbutanoate

Synonyms

4-PBA sodium; Sodium 4-phenylbutyrate; Sodium phenylbutyrate; 4-phenylbutyrate (4-PBA); 4-phenylbutyric acid; Buphenyl

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: ~30 mg/mL (~161.1 mM)

Water: <1 mg/mL

Ethanol: ~8 mg/mL (~43.0 mM)

Solubility (In Vivo)

Chemical Name:sodium 4-phenylbutanoate

InChi Key:VPZRWNZGLKXFOE-UHFFFAOYSA-M

InChi Code:InChI=1S/C10H12O2.Na/c11-10(12)8-4-7-9-5-2-1-3-6-9;/h1-3,5-6H,4,7-8H2,(H,11,12);/q;+1/p-1

SMILES Code:O=C([O-])CCCC1=CC=CC=C1.[Na+]

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.3711 mL	26.8557 mL	53.7115 mL
	5 mM	1.0742 mL	5.3711 mL	10.7423 mL
	10 mM	0.5371 mL	2.6856 mL	5.3711 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
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See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

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Concentration (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT06069375	Recruiting	Drug: Sodium phenylbutyrate	Medium-chain Acyl-CoA Dehydrogenase Deficiency	Jerry Vockley, MD, PhD	December 2023	Phase 2
NCT02111200	Completed	Drug: Sodium Phenylbutyrate Drug: Sodium Benzoate	Urea Cycle Disorders, Inborn	Baylor College of Medicine	September 2014	Not Applicable
NCT01529060	Completed	Drug: Phenylbutyrate Drug: Placebo powder	Maple Syrup Urine Disease	Brendan Lee	February 2013	Phase 2 Phase 3
NCT00107770	Completed	Drug: sodium phenylbutyrate	Amyotrophic Lateral Sclerosis	US Department of Veterans Affairs	April 2005	Phase 1 Phase 2

Biological Data

Effects of administration of phenylbutyrate starting at 75 days of age on survival in the N171-82Q transgenic mouse model of HD.J Biol Chem.2005 Jan 7;280(1):556-63.

Sodium Phenylbutyrate — Western blots showing the effects of phenylbutyrate treatment (100 mg/kg intraperitoneal) on histone acetylation in the brain of N171-82Q at 0, 1, 2, 3, and 4 h after administration.J Biol Chem.2005 Jan 7;280(1):556-63.