Sodium Phenylbutyrate

HCID 5258CAS 1716-12-7
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C([O-])CCCc1ccccc1.[Na+]
InChIKey
VPZRWNZGLKXFOE-UHFFFAOYSA-M
Molecular formula
C10H11NaO2
Average molar mass
186.18 g/mol
Monoisotopic mass
186.06567387

Overview

Sodium phenylbutyrate is the organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders. It has a role as a geroprotector, a prodrug, an EC 3.5.1.98 (histone deacetylase) inhibitor, a neuroprotective agent and an orphan drug. It contains a 4-phenylbutyrate.

Names & identifiers

Preferred name
Sodium Phenylbutyrate
IUPAC
sodium 4-phenylbutanoate
English name
Sodium 4-phenylbutyrate
Molecular formula
C10H13NaO2
Molecular weight
188.2

Names & synonyms

Sodium 4-phenylbutyrateSODIUM PHENYLBUTYRATE1716-12-7BuphenylTriButyrateBenzenebutanoic acid, sodium saltAmmonapsPheburane4-phenylbutyric acid, sodium saltOLPRUVADTXSID7040948NT6K61736T
Show more names
PBNA4PBA4-PHENYLBUTYRATENsc6578024PBA SODIUM4-PHENYLBUTYRATE, NASodium 4-Phenylbutyr
ACER-001NSC-657802DTXCID5020948CHEBI:75316RELYVRIO COMPONENT SODIUM PHENYLBUTYRATEAMX0035 COMPONENT SODIUM PHENYLBUTYRATEAmbutyrateRefChem:56033

Database identifiers

CAS
1716-12-7
PubChem CID
5258
DTXSID
DTXSID7040948
ChEMBL
CHEMBL1333672、CHEMBL1746
ChEBI
CHEBI:75316
UNII
NT6K61736T
EC Number
605-612-7
Nikkaji
J783.828J

Properties

Computed structural properties

Topological polar surface area
40.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
13

Experimental & physicochemical properties

Human Drugs · 5 items

Breast Feeding; Lactation; Milk, Human; Urea Cycle Disorders

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point
224 · 224-226°C (dec.)
storage temp.
room temp
solubility
2 O: · H2O: ≥5mg/mL
form
White to slightly yellow solid
color
white to beige
Water Solubility
10 mg/mL · water: 10mg/mL

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 2.3% (1 of 44) of reports.

Warning

H319 (93.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesEye Irrit. 2 (93.2%)

Toxicology

Hepatotoxicity · 1 item

While the urea cycle disorders are caused by deficiencies of hepatic enzymes responsible for the elimination of nitrogen, patients generally present with hyperammonemia without other features or biochemical evidence of hepatic injury. Thus, serum aminotransferase, alkaline phosphatase and bilirubin levels are generally normal or only mildly elevated. Newborns presenting with hyperammonemia may have hepatomegaly but other, non-urea cycle, liver function is normal as is hepatic histology. Phenylbutyrate can help to lower ammonia levels acutely and manage to keep them in the normal or near normal range, but generally does not affect other liver functions. In open label studies, a small proportion of patients (particularly with ornithine transcarbamylase [OTC] deficiency) have had ALT or AST elevations, but these have generally been attributed to the underlying condition or its complications. Phenylbutyrate has not been linked to instances of clinically apparent liver injury with jaundice.

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Sodium phenylbutyrate

Ambiguous-DILI-concern

4

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
rtecs
CY9057220
hs_code
29163990
risk_code
36
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

ATC Code · 2 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

FDA Pharmacological Classification · 4 items

SODIUM PHENYLBUTYRATE

Ammonium Ion Binding Activity [MoA]; Nitrogen Binding Agent [EPC]

SODIUM PHENYLBUTYRATE TABLETS, 500 MG

Ammonium Ion Binding Activity [MoA]; Nitrogen Binding Agent [EPC]

MeSH Pharmacological ClassificationSubstances that inhibit or prevent the proliferation of NEOPLASMS.
Applications · 6 items

DescriptionSodium 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.

DescriptionSodium 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.

UsesACE 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.

UsesSodium 4-Phenylbutyrate is a histone-deacetylase inhibitor.

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

General DescriptionAn 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.

Upstream & downstream products

Suppliers50 total

常州帝通化工有限公司+86-0519-88298848 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Additional notes

DefinitionChEBI: The organic sodium salt of 4-phenylbutyric acid. A prodrug for phenylacetate, it is used to treat urea cycle disorders.

Related reactions

5 records
New reaction record

Linked notes

Loading…