Sodium phenylacetate

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

Structure Search

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

HIDE SMILES / InChI

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

Description
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

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle 3 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205880Orig1s000lbl.pdf	Primary		Approved 8583	AMMONUL Approved Use Sodium 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 Date 2005
Recurrent or progressive brain tumors 3 Sources: https://clinicaltrials.gov/ct2/show/NCT00003241	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

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	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	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	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	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	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	SODIUM BENZOATE	PHENYLACETYLGLUTAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf	unhealthy, 0 - 53 Health Status: unhealthy Age Group: 0 - 53 Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf	Disc. AE: Metabolic acidosis, Injection site reactions... AEs leading to discontinuation/dose reduction: Metabolic acidosis (< 1%) 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%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf	Other AEs: Neurotoxicity... Other AEs: Neurotoxicity Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8 1057 CYP2C19 2057 CYP3A4/5 296 MRP4 290 BCRP 910	UGT 219	CYP1A2 832 CYP3A4/5 133

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23017367/	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	weak
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	weak
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	weak
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	yes [Ki 15000 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=34 Page: 34.0	yes
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	yes
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	yes
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=34 Page: 34.0	yes
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23017367/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/23017367/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=26 Page: 26.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:30745	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:30745
eMolecules	495300	https://www.emolecules.com/cgi-bin/more?vid=495300
ZINC	ZINC000000388462	http://zinc15.docking.org/substances/ZINC000000388462

PubMed

Title	Date	PubMed
Serum paraoxonase: effect of the apolipoprotein composition of HDL and the acute phase response.	2003-04	12562837
Environmental effects caused by olive mill wastewaters: toxicity comparison of low-molecular-weight phenol components.	2003-02-12	12568563
Structure-activity relationships of novel anti-malarial agents: part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides.	2003-02-10	12565929
Paraoxonase and susceptibility to organophosphorus poisoning in farmers dipping sheep.	2003-02	12563177
Potent sigma 1-receptor ligand 4-phenyl-1-(4-phenylbutyl) piperidine provides ischemic neuroprotection without altering dopamine accumulation in vivo in rats.	2003-02	12538208
A new phenylacetate-bisphosphonate inhibits breast cancer cell growth by proapoptotic and antiangiogenic effects.	2003-01-30	12553014
Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages.	2003-01-27	12569517
Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism.	2002-12-30	12507404
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.	2002-12-05	12213291
Genomic analysis of the aromatic catabolic pathways from Pseudomonas putida KT2440.	2002-12	12534466
Metabolic physiology of aroma-producing Kluyveromyces marxianus.	2002-11	12402244
beta-Cell adaptation to insulin resistance. Increased pyruvate carboxylase and malate-pyruvate shuttle activity in islets of nondiabetic Zucker fatty rats.	2002-10-18	12147706
Arginine 165/arginine 277 pair in (S)-mandelate dehydrogenase from Pseudomonas putida: role in catalysis and substrate binding.	2002-10-15	12369819
Development and substantiation of a liquid chromatographic method for monitoring organic reactions involved in synthesis of 4-methoxyphenylacetic acid.	2002-10-04	12416886
Successful treatment of severe hyperammonemia using sodium phenylacetate powder prepared in hospital pharmacy.	2002-09	12230130
[Treatment of methicillin-resistant Staphylococcus aureus (MRSA) as part of biosurgical management of a chronic leg ulcer].	2002-09	12207265
Aerobic metabolism of phenylacetic acids in Azoarcus evansii.	2002-09	12189419
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.	2002-08-15	12182763
Characterization of tropane alkaloid aromatic esters that reverse the multidrug-resistance phenotype.	2002-08-10	12168815
Application of molecular genetics to the diagnosis of lymphoid-rich effusions: study of 95 cases with concomitant immunophenotyping.	2002-08	12203875
Correlation between microbial enzyme activities in the rumen fluid of sheep under different treatments.	2002-07-20	12126297
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry.	2002-07-01	12062658
The cefT gene of Acremonium chrysogenum C10 encodes a putative multidrug efflux pump protein that significantly increases cephalosporin C production.	2002-07	12172807
Molecular analysis of aerobic phenylacetate degradation in Azoarcus evansii.	2002-07	12172805
Polarization IR spectra of the hydrogen bond in phenylacetic acid crystals: H/D isotopic effects temperature and polarization effects.	2002-07	12164486
Identification of phenylbutyrylglutamine, a new metabolite of phenylbutyrate metabolism in humans.	2002-06	12112740
Immunosuppressant-like effects of phenylbutyrate on growth inhibition of Saccharomyces cerevisiae.	2002-06	12111095
Paraoxonase Gln-Arg(192) and Leu-Met(55) gene polymorphisms and enzyme activity in a population with a low rate of coronary heart disease.	2002-05	12074827
Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.	2002-05	11988514
Fermentation of cottonseed and other feedstuffs in cattle rumen fluid.	2002-04-10	11929282
Serum paraoxonase activity changes in patients with Alzheimer's disease and vascular dementia.	2002-04	12111338
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.	2002-04	11985586
New glycosides from the Japanese fern Hymenophyllum barbatum.	2002-04	11963999
Aponecrotic, antiangiogenic and antiproliferative effects of a novel dextran derivative on breast cancer growth in vitro and in vivo.	2002-04	11959788
Effects of cryopreservation and phenylacetate on biological characters of adherent LAK cells from patients with hepatocellular carcinoma.	2002-04	11925598
Induction and repression of the sty operon in Pseudomonas putida CA-3 during growth on phenylacetic acid under organic and inorganic nutrient-limiting continuous culture conditions.	2002-03-05	11959447
[Up regulation of phenylacetate to glioma homeobox gene expression].	2002-03	12015031
Emended descriptions of the genus Micrococcus, Micrococcus luteus (Cohn 1872) and Micrococcus lylae (Kloos et al. 1974).	2002-03	11931177
Structure-activity relationships of novel anti-malarial agents. Part 3: N-(4-acylamino-3-benzoylphenyl)-4-propoxycinnamic acid amides.	2002-02-25	11844668
Atorvastatin preferentially reduces LDL-associated platelet-activating factor acetylhydrolase activity in dyslipidemias of type IIA and type IIB.	2002-02-01	11834533
Pheromone components of the wheat stem sawfly: identification, electrophysiology, and field bioassay.	2002-02	11925076
Studies on a soft glycopyrrolate analog, SG-1.	2002-02	11878191
Investigations into tumor accumulation and peroxisome proliferator activated receptor binding by F-18 and C-11 fatty acids.	2002-02	11823126
Growth inhibition of human melanoma tumor cells by the combination of sodium phenylacetate (NaPA) and substituted dextrans and one NaPA-dextran conjugate.	2002-01	11914639
[Penicillin G acylase--synthesis, regulation, production].	2002-01	11910744
Aromatic amino acid biosynthesis and production of related compounds from p-hydroxyphenylpyruvic acid by rumen bacteria, protozoa and their mixture.	2002	12395184
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	12058401
[Determination of organic acids in cigarette smoke].	2001-07	12545508
[Studies on the immobilized penicillin acylase on polymer beads].	2001-04	12549027
[Determination of degraded products of penicillin by high performance liquid chromatography].	2001-01	12541856

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:16:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:16:17 GMT 2025`
Record UNII	48N6U1781G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-3039

Preferred Name

English

Sodium phenylacetate

Official Name

English

SODIUM PHENYLACETATE [MART.]

Common Name

English

UCEPHAN COMPONENT SODIUM PHENYLACETATE

Common Name

English

SODIUM PHENYLACETATE [JAN]

Common Name

English

SODIUM PHENYLACETATE [HSDB]

Common Name

English

AMMONUL COMPONENT SODIUM PHENYLACETATE

Common Name

English

SODIUM PHENYLACETATE [USAN]

Common Name

English

SODIUM PHENYLACETATE [ORANGE BOOK]

Common Name

English

SODIUM PHENYLACETIC ACID

Common Name

English

Sodium phenylacetate [WHO-DD]

Common Name

English

SODIUM PHENYLACETATE [VANDF]

Common Name

English

SODIUM BENZENEACETATE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

197804