Phenylacetic acid
Identification
- Name
- Phenylacetic acid
- Accession Number
- DB09269
- 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Phenylacetic acid (DB09269)
- 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- 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
- 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.
Drug Interaction Unlock Additional DataBeclomethasone dipropionate The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Beclomethasone dipropionate. Betamethasone The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Betamethasone. Betamethasone phosphate The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Betamethasone phosphate. Budesonide The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Budesonide. Ciclesonide The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Ciclesonide. Clobetasol The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Clobetasol. Clobetasol propionate The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Clobetasol propionate. Corticotropin The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Corticotropin. Cortisone acetate The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Cortisone acetate. Deflazacort The therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Deflazacort. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Sodium phenylacetate 48N6U1781G 114-70-5 HZOREEUASZHZBI-UHFFFAOYSA-M - Active Moieties
Name Kind UNII CAS InChI Key Sodium cation ionic LYR4M0NH37 17341-25-2 FKNQFGJONOIPTF-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ammonul Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Cangene Bio Pharma 2005-02-01 2010-02-18 US 
Ammonul Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Bausch Health US LLC 2005-02-17 Not applicable US Ammonul Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Ucyclyd Pharma Inc. 2005-02-17 Not applicable US SODIUM PHENYLACETATE and SODIUM BENZOATE Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Ailex Pharmaceuticals, Llc 2016-02-24 Not applicable US Sodium Phenylacetate and Sodium Benzoate Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Zydus Pharmaceuticals Usa, Inc. 2016-09-01 Not applicable US Sodium Phenylacetate and sodium benzoate Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Navinta Llc 2019-05-07 Not applicable US Sodium Phenylacetate and Sodium Benzoate Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Mylan Institutional LLC 2017-05-23 Not applicable US Sodium Phenylacetate and Sodium Benzoate Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Maia Pharmaceuticals, Inc 2017-05-22 Not applicable US Sodium Phenylacetate and Sodium Benzoate Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Oceanside Pharmaceuticals 2017-03-15 Not applicable US SODIUM PHENYLACETATE and SODIUM BENZOATE Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Trigen Laboratories, LLC 2016-02-24 Not applicable US
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)
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
- External Links
- Human Metabolome Database
- HMDB0000209
- KEGG Compound
- C07086
- PubChem Compound
- 999
- PubChem Substance
- 310265164
- ChemSpider
- 10181341
- BindingDB
- 16419
- 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
Phase Status Purpose Conditions Count 2 Completed Treatment Amino Acid Metabolism, Inborn Errors 1 2 Terminated Treatment Hepatic Encephalopathy (HE) 1 1 Completed Treatment Healthy Volunteers 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution, concentrate Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 3.61 mg/mL ALOGPS logP 1.72 ALOGPS logP 1.61 ChemAxon logS -1.6 ALOGPS pKa (Strongest Acidic) 4.55 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 37.37 m3·mol-1 ChemAxon Polarizability 13.85 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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 27, 2015 21:42 / Updated on June 12, 2020 10:52
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