Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H7O2.Na |
Molecular Weight | 158.1297 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[O-]C(=O)CC1=CC=CC=C1
InChI
InChIKey=HZOREEUASZHZBI-UHFFFAOYSA-M
InChI=1S/C8H8O2.Na/c9-8(10)6-7-4-2-1-3-5-7;/h1-5H,6H2,(H,9,10);/q;+1/p-1
Molecular Formula | Na |
Molecular Weight | 22.98976928 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C8H7O2 |
Molecular Weight | 135.14 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB09269Curator's Comment: description was created based on several sources, including:
https://clinicaltrials.gov/ct2/show/NCT00003241?term=Phenylacetic+acid&rank=3
https://en.wikipedia.org/wiki/Phenylacetic_acid
Sources: http://www.drugbank.ca/drugs/DB09269
Curator's Comment: description was created based on several sources, including:
https://clinicaltrials.gov/ct2/show/NCT00003241?term=Phenylacetic+acid&rank=3
https://en.wikipedia.org/wiki/Phenylacetic_acid
Phenylacetic acid (abr. PAA and synonyms are: α-toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid, β-phenylacetic acid) is an organic compound containing a phenyl functional group and acarboxylic acid functional group. 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 Phenylacetic acid is used in some perfumes, possessing a honey-like odor in low concentrations, and is also used in penicillin G production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then secreted by the patient's body. In Phase 2 of clinical research it investigated in the treatment of Brain and Central Nervous System Tumors.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=935645
Curator's Comment: Known to be CNS penetrant in cat. Human data not available.
Labeled phenylacetic acid (14C-PAA) penetrates blood-cerebrospinal fluid (CSF) barrier in cats only under a high gradient of concentration
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMMONUL Approved UseSodium Phenylacetate and Sodium Benzoate Injection, 10%/10% is a nitrogen binding agent indicated as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle. Launch Date2005 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2225 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15050977/ |
3.75 g/m² single, intravenous dose: 3.75 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: SODIUM BENZOATE |
PHENYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3022 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15050977/ |
5.5 g/m² single, intravenous dose: 5.5 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: SODIUM BENZOATE |
PHENYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
281 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15050977/ |
3.75 g/m² single, intravenous dose: 3.75 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: SODIUM BENZOATE |
PHENYLACETYLGLUTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15004 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15050977/ |
3.75 g/m² single, intravenous dose: 3.75 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: SODIUM BENZOATE |
PHENYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
28156 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15050977/ |
5.5 g/m² single, intravenous dose: 5.5 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: SODIUM BENZOATE |
PHENYLACETIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2047 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15050977/ |
3.75 g/m² single, intravenous dose: 3.75 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: SODIUM BENZOATE |
PHENYLACETYLGLUTAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.44% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8946671/ |
SODIUM PHENYLACETATE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Disc. AE: Metabolic acidosis, Injection site reactions... AEs leading to discontinuation/dose reduction: Metabolic acidosis (< 1%) Sources: Injection site reactions (< 1%) Bradycardia (0.32%) Abdominal distension (0.32%) Injection site extravasation (0.32%) Hemorrhage injection site (0.32%) Blister (0.32%) Subdural hematoma (0.32%) Hyperammonemia (0.32%) Hypoglycemia (0.32%) Clonus (0.32%) Coma (0.32%) Increased intracranial pressure (0.32%) Hypercapnia (0.32%) Kussmaul respiration (0.32%) Respiratory distress (0.32%) Respiratory failure (0.32%) Pruritis (0.32%) Maculo-papular rash (0.32%) |
300 mg/kg 1 times / day multiple, intravenous Recommended Dose: 300 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Neurotoxicity... Other AEs: Neurotoxicity Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal distension | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Blister | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Bradycardia | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Clonus | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Coma | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Hemorrhage injection site | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Hyperammonemia | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Hypercapnia | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Hypoglycemia | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Increased intracranial pressure | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Injection site extravasation | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Kussmaul respiration | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Maculo-papular rash | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Pruritis | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Respiratory distress | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Respiratory failure | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Subdural hematoma | 0.32% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Injection site reactions | < 1% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Metabolic acidosis | < 1% Disc. AE |
5.5 g/m2 1 times / day multiple, intravenous Recommended Dose: 5.5 g/m2, 1 times / day Route: intravenous Route: multiple Dose: 5.5 g/m2, 1 times / day Sources: |
unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: |
Neurotoxicity | 300 mg/kg 1 times / day multiple, intravenous Recommended Dose: 300 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg/kg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=26 Page: 26.0 |
PubMed
Title | Date | PubMed |
---|---|---|
The glutathione metabolism of the beta-lactam producer filamentous fungus Penicillium chrysogenum. | 2001 |
|
Penicillin productivity and glutathione-dependent detoxification of phenylacetic and phenoxyacetic acids in Penicillium chrysogenum. | 2001 |
|
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries. | 2001 |
|
Magnetic resonance pharmacoangiography to detect and predict chemotherapy delivery to solid tumors. | 2001 Apr 1 |
|
Differential gene regulation in human versus rodent hepatocytes by peroxisome proliferator-activated receptor (PPAR) alpha. PPAR alpha fails to induce peroxisome proliferation-associated genes in human cells independently of the level of receptor expresson. | 2001 Aug 24 |
|
New bitter-tasting hemiterpene glycosides from the Japanese fern Hymenophyllum barbatum. | 2001 Dec |
|
Modulation of the multidrug-resistance phenotype by new tropane alkaloid aromatic esters from Erythroxylum pervillei. | 2001 Dec |
|
[Determination of degraded products of penicillin by high performance liquid chromatography]. | 2001 Jan |
|
Alternative pathway therapy for urea cycle disorders: twenty years later. | 2001 Jan |
|
Current strategies for the management of neonatal urea cycle disorders. | 2001 Jan |
|
Effects of 5' regulatory-region polymorphisms on paraoxonase-gene (PON1) expression. | 2001 Jun |
|
Lovastatin and phenylacetate induce apoptosis, but not differentiation, in human malignant glioma cells. | 2001 Mar |
|
The phenylacetyl-CoA catabolon: a complex catabolic unit with broad biotechnological applications. | 2001 Mar |
|
Could 99mTc-MIBI be used to visualize the apoptotic MCF7 human breast cancer cells? | 2001 May |
|
Differentiation of human neuroblastoma by phenylacetate is mediated by peroxisome proliferator-activated receptor gamma. | 2001 May 15 |
|
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines. | 2001 Oct |
|
Clean-chemistry synthesis of 2-tetralones in a single-stage acylation-cycloalkylation process. | 2001 Oct 19 |
|
Aromatic amino acid biosynthesis and production of related compounds from p-hydroxyphenylpyruvic acid by rumen bacteria, protozoa and their mixture. | 2002 |
|
Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism. | 2002 Dec 30 |
|
Volatile flavor components of stored nonfat dry milk. | 2002 Jan 16 |
|
Paraoxonase Gln-Arg(192) and Leu-Met(55) gene polymorphisms and enzyme activity in a population with a low rate of coronary heart disease. | 2002 May |
|
Metabolic physiology of aroma-producing Kluyveromyces marxianus. | 2002 Nov |
|
Arginine 165/arginine 277 pair in (S)-mandelate dehydrogenase from Pseudomonas putida: role in catalysis and substrate binding. | 2002 Oct 15 |
|
beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats. | 2002 Oct 18 |
|
Development and substantiation of a liquid chromatographic method for monitoring organic reactions involved in synthesis of 4-methoxyphenylacetic acid. | 2002 Oct 4 |
|
[Treatment of methicillin-resistant Staphylococcus aureus (MRSA) as part of biosurgical management of a chronic leg ulcer]. | 2002 Sep |
|
Potent sigma 1-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine provides ischemic neuroprotection without altering dopamine accumulation in vivo in rats. | 2003 Feb |
|
Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages. | 2003 Jan 27 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:16:17 GMT 2025
by
admin
on
Mon Mar 31 18:16:17 GMT 2025
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Record UNII |
48N6U1781G
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
197804
Created by
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DEA NO. |
8791
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EU-Orphan Drug |
EU/3/19/2166
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NCI_THESAURUS |
C78275
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DTXSID8059427
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48N6U1781G
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56510
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DBSALT001277
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AA-69
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5581
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23690424
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SUB15315MIG
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C66723
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204-052-7
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48N6U1781G
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3039
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CHEMBL1200358
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100000078120
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114-70-5
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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