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	22.9898
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 2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205880Orig1s000lbl.pdf	Primary		Approved 8360	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 1.10851195E12
Recurrent or progressive brain tumors 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00003241	Primary		Phase II 1144	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 Co-administed with:: Sodium Benzoate, i.v(5.5 g/m2) Arginine HCl, i.v(200-600 mg/kg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf Page: p.11	unhealthy, 0 - 53 n = 316 Health Status: unhealthy Condition: Hyperammonemia Age Group: 0 - 53 Sex: M+F Population Size: 316 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf Page: p.11	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 Page: p.11
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) Arginine HCl, i.v(200-600 mg/kg) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf Page: p.8	unhealthy Health Status: unhealthy Condition: Cancer Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf Page: p.8	Other AEs: Neurotoxicity... Other AEs: Neurotoxicity Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/020645lbl.pdf Page: p.8

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1752	inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1509 CYP2C8 901 CYP2C19 1463 CYP3A4/5 273 MRP4 203 BCRP 691	UGT 187	CYP1A2 689 CYP3A4/5 120

Drug as perpetrator

Target	Modality	Activity
BCRP 765	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23017367/	no
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	weak
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	weak
CYP3A4/5 330	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	weak
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	yes [Ki 15000 uM]
CYP1A2 1673	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=34 Page: 34.0	yes
CYP1A2 1673	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	yes
CYP2C8 955	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=35 Page: 35.0	yes
CYP3A4/5 330	inducer 1542 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203284Orig1s000PharmR.pdf#page=34 Page: 34.0	yes
MRP4 237	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/23017367/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGT 187	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/23017367/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 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
ZINC	ZINC000000388462	http://zinc15.docking.org/substances/ZINC000000388462
eMolecules	495300	https://www.emolecules.com/cgi-bin/more?vid=495300

PubMed

Title	Date	PubMed
The glutathione metabolism of the beta-lactam producer filamentous fungus Penicillium chrysogenum.	2001	11791340
Aceclofenac: a reappraisal of its use in the management of pain and rheumatic disease.	2001	11511027
Penicillin productivity and glutathione-dependent detoxification of phenylacetic and phenoxyacetic acids in Penicillium chrysogenum.	2001	11441461
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
Prostate cancer prevention strategies using antiproliferative or differentiating agents.	2001 Apr	11295601
Decreased stability of the M54 isoform of paraoxonase as a contributory factor to variations in human serum paraoxonase concentrations.	2001 Apr	11290824
Magnetic resonance pharmacoangiography to detect and predict chemotherapy delivery to solid tumors.	2001 Apr 1	11306485
A phase I dose escalation and bioavailability study of oral sodium phenylbutyrate in patients with refractory solid tumor malignancies.	2001 Aug	11489804
Expression and purification of extracellular penicillin G acylase in Bacillus subtilis.	2001 Feb	11162387
[Determination of degraded products of penicillin by high performance liquid chromatography].	2001 Jan	12541856
Current strategies for the management of neonatal urea cycle disorders.	2001 Jan	11148547
[Determination of organic acids in cigarette smoke].	2001 Jul	12545508
Aroma-active components of nonfat dry milk.	2001 Jun	11409991
Effects of 5' regulatory-region polymorphisms on paraoxonase-gene (PON1) expression.	2001 Jun	11335891
Decrease of breast cancer cell invasiveness by sodium phenylacetate (NaPa) is associated with an increased expression of adhesive molecules.	2001 Mar 23	11259095
Could 99mTc-MIBI be used to visualize the apoptotic MCF7 human breast cancer cells?	2001 May	11441954
Differentiation of human neuroblastoma by phenylacetate is mediated by peroxisome proliferator-activated receptor gamma.	2001 May 15	11358817
Phenylethylamine, a possible link to the antidepressant effects of exercise?	2001 Oct	11579070
Inhibitors of histone deacetylase as new anticancer agents.	2001 Oct	11562279
Oxygen dependency of monoamine oxidase activity in the intact lung.	2001 Oct	11557601
Clean-chemistry synthesis of 2-tetralones in a single-stage acylation-cycloalkylation process.	2001 Oct 19	11597238
A chemostat culture as a tool for the improvement of a recombinant E. coli strain over-producing penicillin G acylase.	2001 Oct 5	11536126
Inhibition of estrogen-dependent breast cell responses with phenylacetate.	2001 Sep 1	11477579
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
Serum paraoxonase activity changes in patients with Alzheimer's disease and vascular dementia.	2002 Apr	12111338
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.	2002 Apr	11985586
Effects of cryopreservation and phenylacetate on biological characters of adherent LAK cells from patients with hepatocellular carcinoma.	2002 Apr	11925598
Fermentation of cottonseed and other feedstuffs in cattle rumen fluid.	2002 Apr 10	11929282
Application of molecular genetics to the diagnosis of lymphoid-rich effusions: study of 95 cases with concomitant immunophenotyping.	2002 Aug	12203875
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.	2002 Aug 15	12182763
Neonatal presentation of ventricular tachycardia and a Reye-like syndrome episode associated with disturbed mitochondrial energy metabolism.	2002 Dec 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 Dec 5	12213291
Pheromone components of the wheat stem sawfly: identification, electrophysiology, and field bioassay.	2002 Feb	11925076
Investigations into tumor accumulation and peroxisome proliferator activated receptor binding by F-18 and C-11 fatty acids.	2002 Feb	11823126
Structure-activity relationships of novel anti-malarial agents. Part 3: N-(4-acylamino-3-benzoylphenyl)-4-propoxycinnamic acid amides.	2002 Feb 25	11844668
Monitoring of enzymatic hydrolysis of penicillin G by pyrolysis-negative ion mass spectrometry.	2002 Jul 1	12062658
Immunosuppressant-like effects of phenylbutyrate on growth inhibition of Saccharomyces cerevisiae.	2002 Jun	12111095
[Up regulation of phenylacetate to glioma homeobox gene expression].	2002 Mar	12015031
Emended descriptions of the genus Micrococcus, Micrococcus luteus (Cohn 1872) and Micrococcus lylae (Kloos et al. 1974).	2002 Mar	11931177
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 Mar 5	11959447
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	12074827
Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.	2002 May	11988514
Metabolic physiology of aroma-producing Kluyveromyces marxianus.	2002 Nov	12402244
Arginine 165/arginine 277 pair in (S)-mandelate dehydrogenase from Pseudomonas putida: role in catalysis and substrate binding.	2002 Oct 15	12369819
Successful treatment of severe hyperammonemia using sodium phenylacetate powder prepared in hospital pharmacy.	2002 Sep	12230130
[Treatment of methicillin-resistant Staphylococcus aureus (MRSA) as part of biosurgical management of a chronic leg ulcer].	2002 Sep	12207265
Serum paraoxonase: effect of the apolipoprotein composition of HDL and the acute phase response.	2003 Apr	12562837
Paraoxonase and susceptibility to organophosphorus poisoning in farmers dipping sheep.	2003 Feb	12563177
Structure-activity relationships of novel anti-malarial agents: part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides.	2003 Feb 10	12565929
Environmental effects caused by olive mill wastewaters: toxicity comparison of low-molecular-weight phenol components.	2003 Feb 12	12568563

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 `Wed Jul 05 23:28:54 UTC 2023` Edited by `admin` on `Wed Jul 05 23:28:54 UTC 2023`
Record UNII	48N6U1781G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Sodium phenylacetate

Official Name

English

SODIUM PHENYLACETATE [MART.]

Common Name

English

SODIUM PHENYLACETATE COMPONENT OF AMMONUL

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 COMPONENT OF UCEPHAN

Common Name

English

Sodium phenylacetate [WHO-DD]

Common Name

English

NSC-3039

Code

English

SODIUM PHENYLACETATE [VANDF]

Common Name

English

SODIUM BENZENEACETATE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

197804