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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C8H7O2.Na
Molecular Weight 158.1297
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Sodium phenylacetate

SMILES

[Na+].[O-]C(=O)CC1=CC=CC=C1

InChI

InChIKey=HZOREEUASZHZBI-UHFFFAOYSA-M
InChI=1S/C8H8O2.Na/c9-8(10)6-7-4-2-1-3-5-7;/h1-5H,6H2,(H,9,10);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H7O2
Molecular Weight 135.14
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://clinicaltrials.gov/ct2/show/NCT00003241?term=Phenylacetic+acid&rank=3 https://en.wikipedia.org/wiki/Phenylacetic_acid

Phenylacetic acid (abr. PAA and synonyms are: α-toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid, β-phenylacetic acid) is an organic compound containing a phenyl functional group and acarboxylic acid functional group. Because it is used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China Phenylacetic acid is used in some perfumes, possessing a honey-like odor in low concentrations, and is also used in penicillin G production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then secreted by the patient's body. In Phase 2 of clinical research it investigated in the treatment of Brain and Central Nervous System Tumors.

CNS Activity

Curator's Comment: Known to be CNS penetrant in cat. Human data not available. Labeled phenylacetic acid (14C-PAA) penetrates blood-cerebrospinal fluid (CSF) barrier in cats only under a high gradient of concentration

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMMONUL

Approved Use

Sodium Phenylacetate and Sodium Benzoate Injection, 10%/10% is a nitrogen binding agent indicated as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle.

Launch Date

2005
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2225 μM
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3022 μM
5.5 g/m² single, intravenous
dose: 5.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
281 μM
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
PHENYLACETYLGLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15004 μM × h
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
28156 μM × h
5.5 g/m² single, intravenous
dose: 5.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2047 μM × h
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
PHENYLACETYLGLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.44%
SODIUM PHENYLACETATE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Disc. AE: Metabolic acidosis, Injection site reactions...
AEs leading to
discontinuation/dose reduction:
Metabolic acidosis (< 1%)
Injection site reactions (< 1%)
Bradycardia (0.32%)
Abdominal distension (0.32%)
Injection site extravasation (0.32%)
Hemorrhage injection site (0.32%)
Blister (0.32%)
Subdural hematoma (0.32%)
Hyperammonemia (0.32%)
Hypoglycemia (0.32%)
Clonus (0.32%)
Coma (0.32%)
Increased intracranial pressure (0.32%)
Hypercapnia (0.32%)
Kussmaul respiration (0.32%)
Respiratory distress (0.32%)
Respiratory failure (0.32%)
Pruritis (0.32%)
Maculo-papular rash (0.32%)
Sources:
300 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 300 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 300 mg/kg, 1 times / day
Sources:
unhealthy
Other AEs: Neurotoxicity...
AEs

AEs

AESignificanceDosePopulation
Abdominal distension 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Blister 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Bradycardia 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Clonus 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Coma 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Hemorrhage injection site 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Hyperammonemia 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Hypercapnia 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Hypoglycemia 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Increased intracranial pressure 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Injection site extravasation 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Kussmaul respiration 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Maculo-papular rash 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Pruritis 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Respiratory distress 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Respiratory failure 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Subdural hematoma 0.32%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Injection site reactions < 1%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Metabolic acidosis < 1%
Disc. AE
5.5 g/m2 1 times / day multiple, intravenous
Recommended
Dose: 5.5 g/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.5 g/m2, 1 times / day
Sources:
unhealthy, 0 - 53
Health Status: unhealthy
Age Group: 0 - 53
Sex: M+F
Sources:
Neurotoxicity
300 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 300 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 300 mg/kg, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
The glutathione metabolism of the beta-lactam producer filamentous fungus Penicillium chrysogenum.
2001
Penicillin productivity and glutathione-dependent detoxification of phenylacetic and phenoxyacetic acids in Penicillium chrysogenum.
2001
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.
2001
Magnetic resonance pharmacoangiography to detect and predict chemotherapy delivery to solid tumors.
2001 Apr 1
Differential gene regulation in human versus rodent hepatocytes by peroxisome proliferator-activated receptor (PPAR) alpha. PPAR alpha fails to induce peroxisome proliferation-associated genes in human cells independently of the level of receptor expresson.
2001 Aug 24
New bitter-tasting hemiterpene glycosides from the Japanese fern Hymenophyllum barbatum.
2001 Dec
Modulation of the multidrug-resistance phenotype by new tropane alkaloid aromatic esters from Erythroxylum pervillei.
2001 Dec
[Determination of degraded products of penicillin by high performance liquid chromatography].
2001 Jan
Alternative pathway therapy for urea cycle disorders: twenty years later.
2001 Jan
Current strategies for the management of neonatal urea cycle disorders.
2001 Jan
Effects of 5' regulatory-region polymorphisms on paraoxonase-gene (PON1) expression.
2001 Jun
Lovastatin and phenylacetate induce apoptosis, but not differentiation, in human malignant glioma cells.
2001 Mar
The phenylacetyl-CoA catabolon: a complex catabolic unit with broad biotechnological applications.
2001 Mar
Could 99mTc-MIBI be used to visualize the apoptotic MCF7 human breast cancer cells?
2001 May
Differentiation of human neuroblastoma by phenylacetate is mediated by peroxisome proliferator-activated receptor gamma.
2001 May 15
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines.
2001 Oct
Clean-chemistry synthesis of 2-tetralones in a single-stage acylation-cycloalkylation process.
2001 Oct 19
Aromatic amino acid biosynthesis and production of related compounds from p-hydroxyphenylpyruvic acid by rumen bacteria, protozoa and their mixture.
2002
Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism.
2002 Dec 30
Volatile flavor components of stored nonfat dry milk.
2002 Jan 16
Paraoxonase Gln-Arg(192) and Leu-Met(55) gene polymorphisms and enzyme activity in a population with a low rate of coronary heart disease.
2002 May
Metabolic physiology of aroma-producing Kluyveromyces marxianus.
2002 Nov
Arginine 165/arginine 277 pair in (S)-mandelate dehydrogenase from Pseudomonas putida: role in catalysis and substrate binding.
2002 Oct 15
beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats.
2002 Oct 18
Development and substantiation of a liquid chromatographic method for monitoring organic reactions involved in synthesis of 4-methoxyphenylacetic acid.
2002 Oct 4
[Treatment of methicillin-resistant Staphylococcus aureus (MRSA) as part of biosurgical management of a chronic leg ulcer].
2002 Sep
Potent sigma 1-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine provides ischemic neuroprotection without altering dopamine accumulation in vivo in rats.
2003 Feb
Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages.
2003 Jan 27
Patents

Sample Use Guides

Unknown
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:16:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:16:17 GMT 2025
Record UNII
48N6U1781G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-3039
Preferred Name English
Sodium phenylacetate
HSDB   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
SODIUM PHENYLACETATE [MART.]
Common Name English
UCEPHAN COMPONENT SODIUM PHENYLACETATE
Common Name English
SODIUM PHENYLACETATE [JAN]
Common Name English
SODIUM PHENYLACETATE [HSDB]
Common Name English
AMMONUL COMPONENT SODIUM PHENYLACETATE
Common Name English
SODIUM PHENYLACETATE [USAN]
Common Name English
SODIUM PHENYLACETATE [ORANGE BOOK]
Common Name English
SODIUM PHENYLACETIC ACID
Common Name English
Sodium phenylacetate [WHO-DD]
Common Name English
SODIUM PHENYLACETATE [VANDF]
Common Name English
SODIUM BENZENEACETATE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 197804
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
DEA NO. 8791
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
EU-Orphan Drug EU/3/19/2166
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
NCI_THESAURUS C78275
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID8059427
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
DAILYMED
48N6U1781G
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
RXCUI
56510
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY RxNorm
DRUG BANK
DBSALT001277
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
USAN
AA-69
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
HSDB
5581
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
PUBCHEM
23690424
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
EVMPD
SUB15315MIG
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
NCI_THESAURUS
C66723
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-052-7
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
FDA UNII
48N6U1781G
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
NSC
3039
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200358
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
SMS_ID
100000078120
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
CAS
114-70-5
Created by admin on Mon Mar 31 18:16:17 GMT 2025 , Edited by admin on Mon Mar 31 18:16:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY