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
- MOL File:
- 1716-12-7.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/4/10 13:06:19
| 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) |
Sodium 4-phenylbutyrate price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | SML0309 | Sodium phenylbutyrate ≥98% (HPLC) | 1716-12-7 | 100MG | ₹9645.08 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 567616 | Sodium 4-Phenylbutyrate - CAS 1716-12-7 - Calbiochem A novel anti-neoplastic agent and transcriptional regulator. | 1716-12-7 | 100MG | ₹9260 | 2022-06-14 | Buy |
| TCI Chemicals (India) | O0511 | Sodium 4-Phenylbutyrate | 1716-12-7 | 1G | ₹5800 | 2022-05-26 | Buy |
| TCI Chemicals (India) | O0511 | Sodium 4-Phenylbutyrate | 1716-12-7 | 5G | ₹16000 | 2022-05-26 | 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.
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.
Definition
ChEBI: The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders.
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.
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].
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 Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| STELLENCE PHARMSCIENCE PVT TLD | +91-9820778787 +91-9820778787 | Bangalore, India | 25 | 58 | Inquiry |
| Global Calcium Pvt Ltd | +91-8050750904 +91-8040554500 | Karnataka, India | 132 | 58 | Inquiry |
| Narmada Organics | +91-9601758907 +91-9409133000 | Gujarat, India | 19 | 58 | Inquiry |
| Sri Krishna Pharmaceuticals Ltd | +91-4027177825 +91-8886992503 | Telangana, India | 13 | 58 | Inquiry |
| SRI KRISHNA PHARMACEUTICALS LTD | +91-40-2720 1101 | New Delhi, India | 11 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| Stellence Pharmscience Private Limited | 08068970604Ext 488 | Karnataka, India | 22 | 58 | Inquiry |
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