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4-phenylbutyric acid is a monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the gamma-globin gene and affects hPPARgamma activation. It has a role as an EC 3.5.1.98 (histone deacetylase) inhibitor, an antineoplastic agent, an apoptosis inducer and a prodrug. It derives from a butyric acid. It is a conjugate acid of a 4-phenylbutyrate.|A monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the γ-globin gene and affects hPPARγ activation.|Phenylbutyric acid is a Nitrogen Binding Agent. The mechanism of action of phenylbutyric acid is as an Ammonium Ion Binding Activity.|Phenylbutyrate and sodium benzoate are orphan drugs approved for the treatment of hyperammonemia in patients with urea cycle disorders, a series of at least 8 rare genetic enzyme deficiencies. The urea cycle is the major pathway of elimination of excess nitrogen including ammonia, and absence of one of the urea cycle enzymes often causes elevations in serum ammonia which can be severe, life-threatening and result in permanent neurologic damage and cognitive deficiencies. Both phenylbutyrate and sodium benzoate act by promoting an alternative pathway of nitrogen elimination. Neither phenylbutyrate nor sodium benzoate have been linked to cases of liver injury either in the form of serum enzyme elevations during therapy or clinically apparent acute liver injury.
4-Phenylbutyric acid is white to slightly yellowish crystalline powder. It is slightly soluble in chloroform and methanol. Its solubility in water is 5.3 g/l (at 40 °C).
4-Phenylbutyric acid (4-PBA) is a small-molecular-weight fatty acid with a terminal aromatic group, and its sodium salt (sodium 4-phenyl butyrate) has been used for the treatment of urea cycle disorders. This molecule is also used for the treatment of sickle cell diseases and thalassemia owing to its ability to activate β-globin transcription. Moreover, 4-PBA is employed as an orally bioavailable agent for the treatment of spinal muscular atrophy (SMA) and tumors.Neuroprotective Effects of 4-phenylbutyric Acid and Its Derivatives: Possible Therapeutics for Neurodegenerative Diseases
Crystallise the acid from pet ether (b 40-60o). [Beilstein 9 IV 1811.]