General
Preferred name
Phenylbutyric acid
Synonyms
SODIUM PHENYLBUTYRATE ()
4-PHENYLBUTYRIC ACID ()
Sodium 4-Phenylbutyrate ()
Buphenyl ()
PHENYLBUTANOIC ACID ()
Benzenebutyric acid ()
phenylbutyrate ()
4-PBA ()
4-PBA (sodium) ()
4-Phenylbutyric acid (sodium) ()
Benzenebutyric acid (sodium) ()
4-PBA, 4-Phenylbutyric acid, NaPB ()
4-Phenylbutyric acid (4-PBA) ()
Sodium 4-Phenylbutyrate ()
Sodium 4-Phenylbutyrate-d11 ()
Pheburane ()
4-phenylbutyric acid, sodium salt ()
Benzenebutanoic acid, sodium salt ()
NSC-657802 ()
SODIUM PHENYLBUTYRATE COMPONENT OF AMX-0035 ()
SODIUM PHENYLBUTYRATE COMPONENT OF AMX0035 ()
Ambutyrate ()
Sodium phenylbutyrate component of relyvrio ()
ACER-001 ()
Ammonaps ()
Olpruva ()
Sodium phenylbutyrate component of albrioza ()
P&D ID
PD001992
CAS
1716-12-7
1821-12-1
1262970-43-3
1392208-11-5
Tags
available
prodrug
drug
obsolete probe
Approved by
FDA
First approval
1996
Drug indication
Urea cycle disorder
Spinocerebellar ataxia type 3
HIV infection
Spinal muscular atrophy
Drug Status
approved
investigational
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PRICE 29
DESCRIPTION Sodium 4-phenylbutyrate (TriButyrate), a transcriptional regulator, reversibly inhibits class I and II histone deacetylases (HDACs )resulting in a global increase in gene expression, decreased cellular proliferation, increased cell differentiation, and the induction of apoptosis in susceptible tumor cell populations.
ABSORPTION Under fasting condition the Cmax of a single orally ingested 5g tablet and 5g powder after 1 hour are respectively 218mcg/ml and 195mcg/ml. ; The effect of food on phenylbutyrate absorption is still unknown.
METABOLISM The overall disposition of sodium phenylbutyrate and its metabolites has not been characterized fully. However, the drug is known to be metabolized to phenylacetate and subsequently to phenylacetylglutamine.; Metabolism of phenylbutyrate occurs mainly in liver and kidney.;
DESCRIPTION The salt, sodium phenylbutyrate (PubChem CID 5258) is an inhibitor of histone deacetylase (HDAC) activity . (GtoPdb)
TOXICITY Clinical adverse reaction: In females who were menstruating, 23% reported amenorrhea or menstrual dysfunction. In all patients, 4% reported a decreased appetite, and body odor issues, and 3% of patients report a taste aversion. Other adverse events that occurred in less than 2% of patients were abdominal pain, gastritis, nausea and vomiting, constipation, rectal bleeding, peptic ulcer disease, pancreatitis, aplastic anemia, ecchymosis, arrhythmia, edema, renal tubular acidosis, depressions, skin rash, headache, syncope, and weight gain occurring in at least one patient. ; Laboratory adverse events: Changes to baseline laboratory values were also observed. The events include: acidosis (14%), alkalosis and hyperchloremia (7%), hypophosphatemia (6%), hyperuricemia and hyperphosphatemia (2%), hypernatremia and hypokalemia (1%), hypoalbuminemia (11%), decreased total protein (3%), increase alkaline phosphate (6%), increased liver transaminases (4%), hyperbilirubinemia (1%), anemia (9%), leukopenia and leukocytosis (4%), thrombocytopenia (3%) and thrombocytosis (1%).
DESCRIPTION 4-Phenylbutyric acid (4-PBA) is an inhibitor of HDAC and endoplasmic reticulum (ER) stress, used in cancer and infection research.
PRICE 29
DESCRIPTION DNA topoisomerase I inhibitor; antitumor (Tocris Bioactive Compound Library)
DESCRIPTION Histone deacetylase inhibitor (Tocriscreen Plus)
DESCRIPTION Histone deacetylase inhibitor (Tocriscreen Total)
DESCRIPTION 4-Phenylbutyric acid is an agent indicated for the adjunctive therapy for the management of chronic urea cycle disorders due to deficiencies in specific enzymes, including the neonatal-onset deficiency and late-onset disease with a history of hyperammonemic encephalopathy. (Enamine Bioactive Compounds)
DESCRIPTION 4-Phenylbutyric acid (Benzenebutyric acid) is a histone deacetylase (HDAC) inhibitor and an endoplasmic reticulum stress (ERS) inhibitor. 4-Phenylbutyric acid can be used to treat urea cycle disorders. (TargetMol Bioactive Compound Library)
Compound Sets
28
Cayman Chemical Bioactives
11323
22085
ChEMBL Approved Drugs
CHEMBL1746
CHEMBL1469
ChEMBL Drugs
CHEMBL1746
CHEMBL1469
Drug Repurposing Hub
DrugBank
DB06819
DrugBank Approved Drugs
DB06819
DrugCentral
24
DrugCentral Approved Drugs
24
DrugMAP
DMXLBCQ
DMBHPDW
DrugMAP Approved Drugs
DMXLBCQ
DrugMatrix
Enamine Bioactive Compounds
EBC-03322
Enamine BioReference Compounds
Guide to Pharmacology
8480
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1746
CHEMBL1469
MedChem Express Bioactive Compound Library
HY-15654
HY-A0281
NCATS Inxight Approved Drugs
7WY7YBI87E
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Obsolete Compounds
phenylbutyrate
ReFrame library
Selleckchem Bioactive Compound Library
sodium-phenylbutyrate
4-phenylbutyric-acid-4-pba-
TargetMol Bioactive Compound Library
T5886
The Spectrum Collection
Tocris Bioactive Compound Library
2682
Tocriscreen Plus
2682
Tocriscreen Total
External IDs
75
Properties
(calculated by RDKit )
Molecular Weight
164.08
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
1
Rotatable Bonds
4
Ring Count
1
Aromatic Ring Count
1
cLogP
2.09
TPSA
37.3
Fraction CSP3
0.3
Chiral centers
0.0
Largest ring
6.0
QED
0.74
Structural alerts
1
historic compounds (Chemical Probes.org)
Obsolete
Related compounds
Custom attributes
(extracted from source data)
Target Type
Enzymes
Target
HDAC
Virus Protease
HDAC1
Apoptosis
Autophagy
Autophagy,HDAC
Primary Target
Non-selective HDACs
MOA
Inhibitor
Apoptosis Inducers
Histone Deacetylase (HDAC) Inhibitors
HDAC inhibitor
Member status
member
Indication
urea cycle disorders
Pathway
Chromatin/Epigenetic
DNA Damage/DNA Repair
Microbiology/virology
Anti-infection
Cell Cycle/DNA Damage
Epigenetics
Source data