Phenylacetic acid

Identification

Summary

Phenylacetic acid is an agent used as an adjunct to treat acute hyperammonemia and associated encephalopathy in adult and pediatric patients with deficiencies in enzymes of the urea cycle.

Brand Names
Ammonul
Generic Name
Phenylacetic acid
DrugBank Accession Number
DB09269
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 136.1479
Monoisotopic: 136.0524295
Chemical Formula
C8H8O2
Synonyms
  • benzeneacetic acid
  • α-toluic acid
  • ω-phenylacetic acid
External IDs
  • FEMA NO. 2878
  • NSC-125718

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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Beclomethasone dipropionateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Beclomethasone dipropionate.
BetamethasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Betamethasone.
Betamethasone phosphateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Betamethasone phosphate.
BudesonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Budesonide.
CiclesonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Ciclesonide.
Clobetasol propionateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Clobetasol propionate.
CorticotropinThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Corticotropin.
Cortisone acetateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Cortisone acetate.
DeflazacortThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Deflazacort.
DesoximetasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Desoximetasone.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Sodium phenylacetate48N6U1781G114-70-5HZOREEUASZHZBI-UHFFFAOYSA-M
Active Moieties
NameKindUNIICASInChI Key
Sodium cationionicLYR4M0NH3717341-25-2FKNQFGJONOIPTF-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AmmonulSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousCangene Bio Pharma2005-02-012010-02-18US flag
AmmonulSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousBausch Health US LLC2005-02-17Not applicableUS flag
AmmonulSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousUcyclyd Pharma Inc.2005-02-17Not applicableUS flag
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)InjectionIntravenousMAIA PHARMACEUTICALS2021-07-01Not applicableUS flag
SODIUM PHENYLACETATE and SODIUM BENZOATESodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousAilex Pharmaceuticals, Llc2016-02-24Not applicableUS flag
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousZydus Pharmaceuticals USA Inc.2021-02-08Not applicableUS flag
SODIUM PHENYLACETATE and SODIUM BENZOATESodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousWoodward Pharma Services Llc2021-05-15Not applicableUS flag
Sodium Phenylacetate and sodium benzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousNavinta Llc2021-03-04Not applicableUS flag
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousMylan Institutional LLC2017-05-23Not applicableUS flag
Sodium Phenylacetate and Sodium BenzoateSodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL)Injection, solution, concentrateIntravenousMaia Pharmaceuticals, Inc2017-05-22Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / Organic oxide / Organic oxygen compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid, benzenes (CHEBI:30745)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
ER5I1W795A
CAS number
103-82-2
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

References

General References
  1. article [Link]
  2. MSDS [Link]
Human Metabolome Database
HMDB0000209
KEGG Compound
C07086
PubChem Compound
999
PubChem Substance
310265164
ChemSpider
10181341
BindingDB
16419
RxNav
33332
ChEBI
30745
ChEMBL
CHEMBL1044
ZINC
ZINC000000388462
PDBe Ligand
PAC
Wikipedia
Phenylacetic_acid
PDB Entries
1fxh / 1k5q / 1pnl / 2ine / 2isf / 2y4n / 3ixl / 4yfb / 5zmq / 6a0m

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAmino Acid Metabolism, Inborn Errors1
2TerminatedTreatmentHepatic Encephalopathy (HE)1
1CompletedTreatmentHealthy Subjects (HS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solution, concentrateIntravenous
InjectionIntravenous
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

Enzymes

Kind
Protein
Organism
Humans
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 28, 2015 03:42 / Updated on May 07, 2021 21:40