U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H8O2
Molecular Weight 136.1479
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLACETIC ACID

SMILES

OC(=O)CC1=CC=CC=C1

InChI

InChIKey=WLJVXDMOQOGPHL-UHFFFAOYSA-N
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

HIDE SMILES / InChI
Molecular Formula C8H8O2
Molecular Weight 136.1479
Charge 0
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

CNS Penetrant
2554
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

1987
111
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2225 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15050977/
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
SODIUM BENZOATE
 PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3022 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15050977/
5.5 g/m² single, intravenous
dose: 5.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
SODIUM BENZOATE
 PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
281 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15050977/
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
SODIUM BENZOATE
 PHENYLACETYLGLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15004 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15050977/
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
SODIUM BENZOATE
 PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
28156 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15050977/
5.5 g/m² single, intravenous
dose: 5.5 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
SODIUM BENZOATE
 PHENYLACETIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2047 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15050977/
3.75 g/m² single, intravenous
dose: 3.75 g/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered: SODIUM BENZOATE
SODIUM BENZOATE
 PHENYLACETYLGLUTAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.44%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8946671/
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
300 mg/kg 1 times / day multiple, intravenous (max)
Recommended
Dose: 300 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 300 mg/kg, 1 times / day
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.8
unhealthy
Health Status: unhealthy
Condition: Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.8
Other AEs: Neurotoxicity...
Other AEs:
Neurotoxicity
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.8
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
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
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
unhealthy, 0 - 53
n = 316
Health Status: unhealthy
Condition: Hyperammonemia
Age Group: 0 - 53
Sex: M+F
Population Size: 316
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.11
Neurotoxicity
300 mg/kg 1 times / day multiple, intravenous (max)
Recommended
Dose: 300 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 300 mg/kg, 1 times / day
Co-administed with::
Sodium Benzoate, i.v(5.5 g/m2)
Arginine HCl, i.v(200-600 mg/kg)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.8
unhealthy
Health Status: unhealthy
Condition: Cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
Page: p.8
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C8
911

CYP2C19
1478

CYP3A4/5
278

MRP4
204

BCRP
699
UGT
192
CYP1A2
701

CYP3A4/5
124
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BCRP
773
 no
CYP2C19
1553
 weak
CYP2D6
1891
 weak
CYP3A4/5
335
 weak
CYP2C9
1819
 yes [Ki 15000 uM]
CYP1A2
1692
 yes
CYP1A2
1692
 yes
CYP2C8
965
 yes
CYP3A4/5
335
 yes
MRP4
238
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT
192
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:30745
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30745
ZINC
ZINC000000388462
http://zinc15.docking.org/substances/ZINC000000388462
eMolecules
495300
https://www.emolecules.com/cgi-bin/more?vid=495300
PubMed

PubMed

TitleDatePubMed
[Studies on the immobilized penicillin acylase on polymer beads].
2001 Apr
[Determination of degraded products of penicillin by high performance liquid chromatography].
2001 Jan
[Determination of organic acids in cigarette smoke].
2001 Jul
Correlation between microbial enzyme activities in the rumen fluid of sheep under different treatments.
2001 Nov-Dec
Aromatic amino acid biosynthesis and production of related compounds from p-hydroxyphenylpyruvic acid by rumen bacteria, protozoa and their mixture.
2002
Evaluation of strains derived from Escherichia coli W as hosts for the expression of penicillin G-acylase-encoding gene cloned on the recombinant plasmid pKA18.
2002
Serum paraoxonase activity changes in patients with Alzheimer's disease and vascular dementia.
2002 Apr
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.
2002 Apr
New glycosides from the Japanese fern Hymenophyllum barbatum.
2002 Apr
Aponecrotic, antiangiogenic and antiproliferative effects of a novel dextran derivative on breast cancer growth in vitro and in vivo.
2002 Apr
Effects of cryopreservation and phenylacetate on biological characters of adherent LAK cells from patients with hepatocellular carcinoma.
2002 Apr
Fermentation of cottonseed and other feedstuffs in cattle rumen fluid.
2002 Apr 10
Application of molecular genetics to the diagnosis of lymphoid-rich effusions: study of 95 cases with concomitant immunophenotyping.
2002 Aug
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.
2002 Aug 15
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440.
2002 Dec
Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism.
2002 Dec 30
4-Fluoro-N-butylphenylacetamide: a synthetic phenylacetate derivative that upregulates Bcl-X(S), activates caspase cascade and induces apoptosis in human squamous lung cancer CH27 cells.
2002 Dec 5
Pheromone components of the wheat stem sawfly: identification, electrophysiology, and field bioassay.
2002 Feb
Studies on a soft glycopyrrolate analog, SG-1.
2002 Feb
Investigations into tumor accumulation and peroxisome proliferator activated receptor binding by F-18 and C-11 fatty acids.
2002 Feb
Atorvastatin preferentially reduces LDL-associated platelet-activating factor acetylhydrolase activity in dyslipidemias of type IIA and type IIB.
2002 Feb 1
Structure-activity relationships of novel anti-malarial agents. Part 3: N-(4-acylamino-3-benzoylphenyl)-4-propoxycinnamic acid amides.
2002 Feb 25
Growth inhibition of human melanoma tumor cells by the combination of sodium phenylacetate (NaPA) and substituted dextrans and one NaPA-dextran conjugate.
2002 Jan
[Penicillin G acylase--synthesis, regulation, production].
2002 Jan
The cefT gene of Acremonium chrysogenum C10 encodes a putative multidrug efflux pump protein that significantly increases cephalosporin C production.
2002 Jul
Molecular analysis of aerobic phenylacetate degradation in Azoarcus evansii.
2002 Jul
Polarization IR spectra of the hydrogen bond in phenylacetic acid crystals: H/D isotopic effects temperature and polarization effects.
2002 Jul
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry.
2002 Jul 1
Identification of phenylbutyrylglutamine, a new metabolite of phenylbutyrate metabolism in humans.
2002 Jun
Immunosuppressant-like effects of phenylbutyrate on growth inhibition of Saccharomyces cerevisiae.
2002 Jun
[Up regulation of phenylacetate to glioma homeobox gene expression].
2002 Mar
Emended descriptions of the genus Micrococcus, Micrococcus luteus (Cohn 1872) and Micrococcus lylae (Kloos et al. 1974).
2002 Mar
Induction and repression of the sty operon in Pseudomonas putida CA-3 during growth on phenylacetic acid under organic and inorganic nutrient-limiting continuous culture conditions.
2002 Mar 5
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
Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.
2002 May
Characterization of tropane alkaloid aromatic esters that reverse the multidrug-resistance phenotype.
2002 May-Jun
Metabolic physiology of aroma-producing Kluyveromyces marxianus.
2002 Nov
A new phenylacetate-bisphosphonate inhibits breast cancer cell growth by proapoptotic and antiangiogenic effects.
2002 Nov-Dec
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
Successful treatment of severe hyperammonemia using sodium phenylacetate powder prepared in hospital pharmacy.
2002 Sep
[Treatment of methicillin-resistant Staphylococcus aureus (MRSA) as part of biosurgical management of a chronic leg ulcer].
2002 Sep
Aerobic metabolism of phenylacetic acids in Azoarcus evansii.
2002 Sep
Serum paraoxonase: effect of the apolipoprotein composition of HDL and the acute phase response.
2003 Apr
Paraoxonase and susceptibility to organophosphorus poisoning in farmers dipping sheep.
2003 Feb
Potent sigma 1-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine provides ischemic neuroprotection without altering dopamine accumulation in vivo in rats.
2003 Feb
Structure-activity relationships of novel anti-malarial agents: part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides.
2003 Feb 10
Environmental effects caused by olive mill wastewaters: toxicity comparison of low-molecular-weight phenol components.
2003 Feb 12
Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages.
2003 Jan 27
Patents

Patents

04065623
3
04455164
4
04481369
4
04532255
5
04587047
4
04797435
3
05238958
3
05382593
3
05399564
3
05405851
8
05474995
4
05616620
13
JP2000186067A
3
JP2000217586A
3
JP2000327622A
3
JP2001139535A
3
JP2002193924A
3
JP2002503209A
3
JP2005500272A
3
JP2006169122A
3
JP2007511203A
5
JP2009051777A
3
JP2011525180A
180
JP4833468B2
3
JPH01175962A
3
JPH01233221A
4
JPH02225470A
3
JPH026434A
3
JPH03223263A
3
JPH03246280A
3
JPH05279425A
3
JPH06116218A
3
JPH06247916A
3
JPH07223995A
3
JPS05735543A
3
JPS51136645A
3
JPS53127444A
3
JPS54157538A
3
JPS5436226A
3
JPS5463041A
3
JPS55111441A
3
JPS5562050A
3
JPS5629542A
3
JPS5640678A
3
JPS5714554A
3
JPS5716840A
3
JPS58206542A
3
JPS5843943A
4
JPS60136516A
3
JPS61286349A
3
JPS63126600A
3

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:18:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:18:30 GMT 2023
Record UNII
ER5I1W795A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENYLACETIC ACID
FCC   FHFI   MI  
Systematic Name English
PHENYLACETIC ACID [MI]
Common Name English
TROPICAMIDE IMPURITY D [EP IMPURITY]
Common Name English
PHENYLACETIC ACID [HSDB]
Common Name English
NSC-125718
Code English
.ALPHA.-TOLUIC ACID
Systematic Name English
FEMA NO. 2878
Code English
BENZYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY B { EP IMPURITY]
Common Name English
PROCAINE BENZYLPENICILLIN IMPURITY E [EP IMPURITY]
Common Name English
.OMEGA.-PHENYLACETIC ACID
Common Name English
PHENYLACETIC ACID [FCC]
Common Name English
BENZYLPENICILLIN SODIUM IMPURITY B [EP IMPURITY]
Common Name English
TROPICAMIDE RELATED COMPOUND D [USP IMPURITY]
Common Name English
ACETIC ACID, PHENYL-
Systematic Name English
2-PHENYLACETIC ACID
Systematic Name English
BENZYLPENICILLIN POTASSIUM IMPURITY B [EP IMPURITY]
Common Name English
ASTUGENAL COMPONENT PHENYLACETIC ACID
Common Name English
PHENYLACETIC ACID [FHFI]
Common Name English
TROPICAMIDE RELATED COMPOUND D [USP-RS]
Common Name English
ANTINEOPLASTON AS2-1 COMPONENT PHENYLACETIC ACID
Common Name English
ANTINEOPLASTON AS 2-1 COMPONENT PHENYLACETIC ACID
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
DEA NO. 8791
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
NDF-RT N0000175807
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
FDA ORPHAN DRUG 267408
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
NDF-RT N0000175806
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
JECFA EVALUATION PHENYLACETIC ACID
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
DEA NO. 8791
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
FDA ORPHAN DRUG 189804
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C77487
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
HSDB
5010
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
WIKIPEDIA
PHENYLACETIC ACID
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
SMS_ID
100000172583
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
MESH
C025136
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1699049
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
CAS
103-82-2
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
DRUG BANK
DB09269
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
DAILYMED
ER5I1W795A
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
CHEBI
30745
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
203-148-6
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
PUBCHEM
999
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
CONCEPT Industrial Aid
FDA UNII
ER5I1W795A
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
DRUG CENTRAL
4624
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID2021656
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
RXCUI
33332
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C1613
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
ALTERNATIVE
MERCK INDEX
m8650
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY Merck Index
JECFA MONOGRAPH
940
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
NSC
125718
Created by admin on Fri Dec 15 15:18:31 GMT 2023 , Edited by admin on Fri Dec 15 15:18:31 GMT 2023
PRIMARY
Related Record Type Details
Structure of Sodium phenylacetate
SALT/SOLVATE -> PARENT
Structure of ORNITHINE PHENYLACETATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of PHENYLBUTYRIC ACID
PRODRUG -> METABOLITE ACTIVE
The active molecule that combines with glutamine (an amino acid with two nitrogen molecules) to form phenylacetylglutamine which is rapidly excreted by the kidneys and does not require metabolism via the urea cycle. Phenylbutyrate thus provides an “ammonia sink”, an alternative pathway for excretion of excess nitrogen and ammonia. The active metabolite phenylacetate is also effective therapeutically, but has a disagreeable odor and taste that affect compliance and acceptability.
Structure of LISDEXAMFETAMINE
PARENT -> METABOLITE
Structure of AMPHETAMINE
PARENT -> METABOLITE
Related Record Type Details
Structure of PENICILLIN G BENZATHINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of TROPICAMIDE
PARENT -> IMPURITY
impurity D at 210 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHYLPHENIDATE HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of PENICILLIN G POTASSIUM
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PENICILLIN G SODIUM
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of TROPICAMIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of PHENYLACETIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966