Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H7O2.H4N |
| Molecular Weight | 153.1784 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[NH4+].[O-]C(=O)CC1=CC=CC=C1
InChI
InChIKey=PQILKFQDIYPBKI-UHFFFAOYSA-N
InChI=1S/C8H8O2.H3N/c9-8(10)6-7-4-2-1-3-5-7;/h1-5H,6H2,(H,9,10);1H3
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.
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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
Disc. AE: Metabolic acidosis, Injection site reactions... AEs leading to discontinuation/dose reduction: Metabolic acidosis (< 1%) Sources: Page: p.11Injection 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 (max) Recommended Dose: 300 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg/kg, 1 times / day Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.8Arginine HCl, i.v(200-600 mg/kg) |
unhealthy Health Status: unhealthy Condition: Cancer Sources: Page: p.8 |
Other AEs: Neurotoxicity... Other AEs: Neurotoxicity Sources: Page: p.8 |
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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| 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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.11Arginine HCl, i.v(200-600 mg/kg) |
unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: Page: p.11 |
| Neurotoxicity | 300 mg/kg 1 times / day multiple, intravenous (max) Recommended Dose: 300 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 300 mg/kg, 1 times / day Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Sources: Page: p.8Arginine HCl, i.v(200-600 mg/kg) |
unhealthy Health Status: unhealthy Condition: Cancer Sources: Page: p.8 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| weak | ||||
| weak | ||||
| weak | ||||
| yes [Ki 15000 uM] | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Diagnosis and follow-up of cystinuria: use of proton magnetic resonance spectroscopy. | 2000 |
|
| Pharmacokinetics of chlorambucil in patients with chronic lymphocytic leukaemia: comparison of different days, cycles and doses. | 2000 Nov |
|
| Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries. | 2001 |
|
| Decreased stability of the M54 isoform of paraoxonase as a contributory factor to variations in human serum paraoxonase concentrations. | 2001 Apr |
|
| Transcriptional regulation of styrene degradation in Pseudomonas putida CA-3. | 2001 Apr |
|
| A phase I dose escalation and bioavailability study of oral sodium phenylbutyrate in patients with refractory solid tumor malignancies. | 2001 Aug |
|
| New bitter-tasting hemiterpene glycosides from the Japanese fern Hymenophyllum barbatum. | 2001 Dec |
|
| Expression and purification of extracellular penicillin G acylase in Bacillus subtilis. | 2001 Feb |
|
| Effects of 5' regulatory-region polymorphisms on paraoxonase-gene (PON1) expression. | 2001 Jun |
|
| The differentiation inducers phenylacetate and phenylbutyrate modulate camptothecin sensitivity in colon carcinoma cells in vitro by intracellular acidification. | 2001 Nov |
|
| Correlation between microbial enzyme activities in the rumen fluid of sheep under different treatments. | 2001 Nov-Dec |
|
| Inhibition of estrogen-dependent breast cell responses with phenylacetate. | 2001 Sep 1 |
|
| Sodium phenylacetate enhances the inhibitory effect of dextran derivative on breast cancer cell growth in vitro and in nude mice. | 2001 Sep 14 |
|
| Evaluation of strains derived from Escherichia coli W as hosts for the expression of penicillin G-acylase-encoding gene cloned on the recombinant plasmid pKA18. | 2002 |
|
| Serum paraoxonase activity changes in patients with Alzheimer's disease and vascular dementia. | 2002 Apr |
|
| Effects of cryopreservation and phenylacetate on biological characters of adherent LAK cells from patients with hepatocellular carcinoma. | 2002 Apr |
|
| Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism. | 2002 Dec 30 |
|
| 4-Fluoro-N-butylphenylacetamide: a synthetic phenylacetate derivative that upregulates Bcl-X(S), activates caspase cascade and induces apoptosis in human squamous lung cancer CH27 cells. | 2002 Dec 5 |
|
| Investigations into tumor accumulation and peroxisome proliferator activated receptor binding by F-18 and C-11 fatty acids. | 2002 Feb |
|
| Volatile flavor components of stored nonfat dry milk. | 2002 Jan 16 |
|
| beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats. | 2002 Oct 18 |
|
| Paraoxonase and susceptibility to organophosphorus poisoning in farmers dipping sheep. | 2003 Feb |
|
| Environmental effects caused by olive mill wastewaters: toxicity comparison of low-molecular-weight phenol components. | 2003 Feb 12 |
|
| Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages. | 2003 Jan 27 |
Patents
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
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Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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81607
Created by
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PX9XBC6PGQ
Created by
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230-551-4
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7188-16-1
Created by
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DTXSID1064588
Created by
admin on Sat Dec 16 13:08:42 GMT 2023 , Edited by admin on Sat Dec 16 13:08:42 GMT 2023
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SUBSTANCE RECORD
