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
Structure for Phenylacetic acid (DB09269)
- Weight
- Average: 136.1479
Monoisotopic: 136.0524295 - Chemical Formula
- C8H8O2
- Synonyms
- .ALPHA.-TOLUIC ACID
- .OMEGA.-PHENYLACETIC ACID
- 2-PHENYLACETIC ACID
- ACETIC ACID, PHENYL-
- ANTINEOPLASTON AS 2-1 COMPONENT PHENYLACETIC ACID
- ANTINEOPLASTON AS2-1 COMPONENT PHENYLACETIC ACID
- ASTUGENAL COMPONENT PHENYLACETIC ACID
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Hyperammonemia Combination Product in combination with: Benzoic acid (DB03793) •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The acute oral LD50 in rats has been documented to be >5000 mg/kg.3
- 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 Integrate drug-drug
interactions in your softwareBeclomethasone 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. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Ucyclyd Pharma Inc. 2005-02-17 Not applicable US 
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 SODIUM PHENYLACETATE and SODIUM BENZOATE Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Woodward Pharma Services Llc 2021-12-15 Not applicable US SODIUM PHENYLACETATE and SODIUM BENZOATE Sodium phenylacetate (100 mg/1mL) + Sodium benzoate (100 mg/1mL) Injection, solution, concentrate Intravenous Woodward Pharma Services Llc 2021-05-15 Not applicable US
Categories
- ATC Codes
- A16AX30 — Sodium benzoate and sodium phenylacetate
- 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
- 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 (HV) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution, concentrate Intravenous Injection 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 128.059747 predictedDarkChem Lite v0.1.0 [M-H]- 128.199847 predictedDarkChem Lite v0.1.0 [M-H]- 128.175847 predictedDarkChem Lite v0.1.0 [M-H]- 123.85602 predictedDeepCCS 1.0 (2019) [M-H]- 128.059747 predictedDarkChem Lite v0.1.0 [M-H]- 128.199847 predictedDarkChem Lite v0.1.0 [M-H]- 128.175847 predictedDarkChem Lite v0.1.0 [M-H]- 123.85602 predictedDeepCCS 1.0 (2019) [M+H]+ 127.02646 predictedDeepCCS 1.0 (2019) [M+H]+ 127.02646 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.09921 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.09921 predictedDeepCCS 1.0 (2019)
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 at October 28, 2015 03:42 / Updated at March 27, 2024 05:12