Identification

Name
Phenylacetic acid
Accession Number
DB09269
Type
Small Molecule
Groups
Approved
Description

Phenylacetic acid is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a disagreeable odor. 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.

Structure
Thumb
Synonyms
  • benzeneacetic acid
  • α-toluic acid
  • ω-phenylacetic acid
External IDs
FEMA NO. 2878 / NSC-125718
Product Ingredients
IngredientUNIICASInChI Key
Sodium phenylacetate48N6U1781G114-70-5HZOREEUASZHZBI-UHFFFAOYSA-M
Active Moieties
NameKindUNIICASInChI Key
Sodium cationionicLYR4M0NH3717341-25-2FKNQFGJONOIPTF-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AmmonulSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousCangene Bio Pharma2005-02-012010-02-18Us
AmmonulSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousUcyclyd Pharma Inc.2005-02-17Not applicableUs
AmmonulSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousValeant Pharmaceuticals North America2005-02-17Not applicableUs
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousMylan Institutional2017-05-23Not applicableUs
SODIUM PHENYLACETATE and SODIUM BENZOATESodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousAilex Pharmaceuticals, Llc2016-02-24Not applicableUs
SODIUM PHENYLACETATE and SODIUM BENZOATESodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousTrigen Laboratories, Inc.2016-02-24Not applicableUs
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousOceanside Pharmaceuticals2017-03-15Not applicableUs
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousMaia Pharmaceuticals, Inc2017-05-22Not applicableUs
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousZydus Pharmaceuticals Usa, Inc.2016-09-01Not applicableUs
Categories
UNII
ER5I1W795A
CAS number
103-82-2
Weight
Average: 136.1479
Monoisotopic: 136.0524295
Chemical Formula
C8H8O2
InChI Key
WLJVXDMOQOGPHL-UHFFFAOYSA-N
InChI
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
IUPAC Name
2-phenylacetic acid
SMILES
OC(=O)CC1=CC=CC=C1

Pharmacology

Indication

For use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution

19.2 ± 3.3 L.

Protein binding
Not Available
Metabolism

Phenylacetate esterases found in the human liver cytosol. Human plasma esterase also hydrolyze phenylacetate. Phenylacetate hydrolysis involved arylesterase in plasma, both arylesterase and carboxylesterase in liver microsomes and carboxylesterase in liver cytosol. Plasma hydrolysis is less important and overall esterase activity is lower in humans than in the rat.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Acute oral toxicity (LD50): 2250 mg/kg [Mouse].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
16-BromoepiandrosteroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 16-Bromoepiandrosterone.
19-norandrostenedioneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 19-norandrostenedione.
5-androstenedioneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 5-androstenedione.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Phenylacetic acid.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Phenylacetic acid.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Phenylacetic acid.
AlclometasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Alclometasone.
AldosteroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Aldosterone.
AlfentanilThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Alfentanil.
AmantadineThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Amantadine.
Food Interactions
Not Available

References

General References
  1. article [Link]
  2. MSDS [Link]
External Links
Human Metabolome Database
HMDB0000209
KEGG Compound
C07086
PubChem Compound
999
PubChem Substance
310265164
ChemSpider
10181341
BindingDB
16419
ChEBI
30745
ChEMBL
CHEMBL1044
HET
PAC
Wikipedia
Phenylacetic_acid
PDB Entries
1fxh / 1k5q / 1pnl / 2ine / 2isf / 2y4n / 3ixl / 4yfb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentAmino Acid Metabolism, Inborn Errors1
2TerminatedTreatmentHepatic Encephalopathy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solution, concentrateIntravenous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.61 mg/mLALOGPS
logP1.72ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.37 m3·mol-1ChemAxon
Polarizability13.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0006-9700000000-c07461cdad68959aa53f
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9100000000-de65c7c0092343a4e599
GC-MS Spectrum - GC-MSGC-MSsplash10-0006-9700000000-c07461cdad68959aa53f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-9700000000-43e86e45beae2fa6704f
Mass Spectrum (Electron Ionization)MSsplash10-0006-9100000000-1e23fd8e6ce900cd8e4c
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0006-9100000000-de65c7c0092343a4e599
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-0006-9000000000-6ca33b098558bf13801c
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000i-0900000000-f898aafe4cecc87d26f1
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Monocyclic benzene moiety / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid, benzenes (CHEBI:30745)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da

Drug created on October 27, 2015 21:42 / Updated on October 01, 2018 16:36