Identification
NamePhenylacetic acid
Accession NumberDB09269
TypeSmall Molecule
GroupsApproved
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 KeyDetails
Sodium phenylacetate48N6U1781G 114-70-5HZOREEUASZHZBI-UHFFFAOYSA-MDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AmmonulInjection, solution, concentrateIntravenousUcyclyd Pharma Inc.2005-02-17Not applicableUs
SODIUM PHENYLACETATE and SODIUM BENZOATEInjection, solution, concentrateIntravenousTrigen Laboratories, Inc.2016-02-24Not applicableUs
Categories
UNIIER5I1W795A
CAS number103-82-2
WeightAverage: 136.1479
Monoisotopic: 136.0524295
Chemical FormulaC8H8O2
InChI KeyWLJVXDMOQOGPHL-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.

Structured Indications
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distribution

19.2 ± 3.3 L.

Protein bindingNot 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 eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

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

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 16-Bromoepiandrosterone.Investigational
19-norandrostenedioneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 19-norandrostenedione.Experimental, Illicit
5-androstenedioneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 5-androstenedione.Experimental, Illicit
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Phenylacetic acid.Approved
AlclometasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Alclometasone.Approved
AldosteroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Aldosterone.Experimental
AmcinonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Amcinonide.Approved
AndrostenedioneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with 4-Androstenedione.Experimental, Illicit
AnecortaveThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Anecortave.Investigational
Beclomethasone dipropionateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Beclomethasone dipropionate.Approved, Investigational
BetamethasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Betamethasone.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Phenylacetic acid.Approved, Investigational
BudesonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Budesonide.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Phenylacetic acid.Approved
CiclesonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Ciclesonide.Approved, Investigational
ClobetasolThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Clobetasol.Investigational
Clobetasol propionateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Clobetasol propionate.Approved
ClocortoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Clocortolone.Approved
Cortisone acetateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Cortisone acetate.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Phenylacetic acid.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Phenylacetic acid.Approved
DesoximetasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Desoximetasone.Approved
Desoxycorticosterone acetateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Desoxycorticosterone acetate.Approved
Desoxycorticosterone PivalateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Desoxycorticosterone Pivalate.Experimental, Vet Approved
DexamethasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Dexamethasone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Dexamethasone isonicotinate.Vet Approved
DiflorasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Diflorasone.Approved
DifluocortoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Difluocortolone.Approved
DifluprednateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Difluprednate.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Phenylacetic acid.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Phenylacetic acid.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Phenylacetic acid.Approved, Investigational
EquileninThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Equilenin.Experimental
EquilinThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Equilin.Approved
EstroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Estrone.Approved
Estrone sulfateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Estrone sulfate.Approved
fluasteroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with fluasterone.Investigational
FludrocortisoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fludrocortisone.Approved
FlumethasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Flumethasone.Approved, Vet Approved
FlunisolideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Flunisolide.Approved, Investigational
Fluocinolone AcetonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluocinolone Acetonide.Approved, Investigational, Vet Approved
FluocinonideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluocinonide.Approved, Investigational
FluocortoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluocortolone.Approved, Withdrawn
FluorometholoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluorometholone.Approved
FluprednideneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluprednidene.Approved, Withdrawn
FluprednisoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluprednisolone.Approved
FlurandrenolideThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Flurandrenolide.Approved
Fluticasone furoateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluticasone furoate.Approved
Fluticasone propionateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Fluticasone Propionate.Approved
FormestaneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Formestane.Approved, Investigational, Withdrawn
HaloperidolThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Haloperidol.Approved
HE3286The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with HE3286.Investigational
HydrocortisoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Hydrocortisone.Approved, Vet Approved
IstaroximeThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Istaroxime.Investigational
ME-609The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with ME-609.Investigational
MedrysoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Medrysone.Approved
MelengestrolThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Melengestrol.Vet Approved
MethylprednisoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Methylprednisolone.Approved, Vet Approved
MometasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Mometasone.Approved, Vet Approved
NCX 1022The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with NCX 1022.Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Phenylacetic acid.Experimental
Oleoyl-estroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Oleoyl estrone.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Phenylacetic acid.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Phenylacetic acid.Approved, Vet Approved
ParamethasoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Paramethasone.Approved
PrasteroneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Prasterone.Approved, Nutraceutical
Prasterone sulfateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with dehydroepiandrosterone sulfate.Investigational
PrednicarbateThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Prednicarbate.Approved
PrednisoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Prednisolone.Approved, Vet Approved
PrednisoneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Prednisone.Approved, Vet Approved
PregnenoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Pregnenolone.Experimental
ProbenecidThe serum concentration of Phenylacetic acid can be increased when it is combined with Probenecid.Approved
RimexoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Rimexolone.Approved
TixocortolThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Tixocortol.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Phenylacetic acid.Approved, Investigational
TriamcinoloneThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Triamcinolone.Approved, Vet Approved
Valproic AcidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Valproic Acid.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. article [Link]
  2. MSDS [Link]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentAmino Acid Metabolism, Inborn Errors1
2TerminatedTreatmentHepatic Encephalopathy1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injection, solution, concentrateIntravenous
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9700000000-c07461cdad68959aa53fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9100000000-de65c7c0092343a4e599View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0006-9700000000-c07461cdad68959aa53fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0006-9700000000-43e86e45beae2fa6704fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e599View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-9000000000-6ca33b098558bf13801cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f898aafe4cecc87d26f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4cView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative ParentsMonocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsMonocyclic 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 FrameworkAromatic homomonocyclic compounds
External Descriptorsmonocarboxylic 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 acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity,...
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 September 01, 2017 12:04