Identification

Name
Phenyl salicylate
Accession Number
DB11071
Type
Small Molecule
Groups
Approved
Description

Phenyl salicylate is a 2-hydroxybenzoic acid phenyl ester. It is utilized in some manufacturing processes of polymers, lacquers, adhesives, waxes, as well as polishes. It is an active ingredient in some pharmaceutical products as a mild analgesic for pain relief by releasing salicylate (found in Aspirin ). Phenyl salicylate may also be found in some antiseptic agents [5]. It is synthesized by heating salicylic acid with phenol [6], [MSDS].

Phenyl salicylate is used as a food additive in the USA [16].

This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone) [14].

Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 3960
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Watkins SettelzPhenyl salicylate (29 mg) + Bismuth Subsalicylate (236 mg) + Pectin (274 mg)LiquidOralWatkins Incorporated1954-12-312011-08-04Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Azuphen MbPhenyl salicylate (36 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (120 mg/1) + Methylene blue trihydrate (10 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2015-09-282016-11-01Us
DarcalmaPhenyl salicylate (36.2 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Sodium phosphate, monobasic, unspecified form (40.8 mg/1)TabletOralRiver's Edge Pharmaceuticals, LLC2008-12-222011-07-31Us
DarcalmaPhenyl salicylate (36.2 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Sodium phosphate, monobasic, unspecified form (40.8 mg/1)TabletOralKylemore Pharmaceuticals, LLC2009-12-012009-12-02Us
DarpazPhenyl salicylate (32.4 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methenamine (81 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Sodium phosphate, monobasic (40.8 mg/1)TabletOralRiver's Edge Pharmaceuticals, LLC2008-12-012011-05-31Us
Hyolev MbPhenyl salicylate (32.4 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1)TabletOralBurel Pharmaceuticals, Llc2015-06-262016-11-01Us
HyophenPhenyl salicylate (36.2 mg/1) + Benzoic Acid (9 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue trihydrate (10.8 mg/1)TabletOralStar Pharmaceuticals, Llc2010-09-21Not applicableUs00076 0901 01 nlmimage10 cc15e64f
MethylphenPhenyl salicylate (36.2 mg/1) + Benzoic Acid (9 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue trihydrate (10.8 mg/1)TabletOralKylemore Pharmaceuticals, LLC2010-01-132010-01-14Us
PhosenaminePhenyl salicylate (36 mg/1) + Hyoscyamine sulfate dihydrate (.12 mg/1) + Methenamine (120 mg/1) + Methylene blue trihydrate (10 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1)CapsuleOralRiver's Edge Pharmaceuticals, LLC2009-01-012011-03-31Us
PhosphasalPhenyl salicylate (36.2 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue trihydrate (10.8 mg/1) + Sodium phosphate, monobasic, monohydrate (40.8 mg/1)TabletOralStar Pharmaceuticals, Llc2010-09-21Not applicableUs
Prosed/DSPhenyl salicylate (36.2 mg/1) + Benzoic Acid (9.0 mg/1) + Hyoscyamine sulfate dihydrate (0.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue trihydrate (10.8 mg/1)TabletOralPhysicians Total Care, Inc.2010-09-152013-01-15Us
Categories
UNII
28A37T47QO
CAS number
118-55-8
Weight
Average: 214.2167
Monoisotopic: 214.062994186
Chemical Formula
C13H10O3
InChI Key
ZQBAKBUEJOMQEX-UHFFFAOYSA-N
InChI
InChI=1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
IUPAC Name
phenyl 2-hydroxybenzoate
SMILES
OC1=CC=CC=C1C(=O)OC1=CC=CC=C1

Pharmacology

Indication

Pain and fever [6].

Pharmacodynamics

Phenyl salicylate has several medical uses. It can be used as an analgesic to relieve pain, as an antiseptic with antibacterial effect as well as a kind of antipyretic for the treatment of fever. It is also used for the treatment of inflammation in the lower urinary tract. It is no longer commonly applied to human medical practice but is still used in veterinary medicine [MSDS].

When it is combined with methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate, it is used to relieve the discomfort, pain, frequent urge to urinate, and cramps/spasms of the urinary tract caused by a urinary tract infection or a diagnostic procedure [8].

Mechanism of action

Inhibits the activity of the enzyme known as cyclooxygenase (COX) which causes the formation of prostaglandins, substances which cause inflammation, swelling, pain, and fever [1]. For more information, refer to the drug entry Aspirin.

TargetActionsOrganism
UProstaglandin G/H synthase 1
antagonist
Human
UProstaglandin G/H synthase 2
antagonist
Human
Absorption

Rapidly absorbed. Refer to Aspirin for detailed salicylate absorption information.

Volume of distribution

Steady-state plasma salicylate concentrations increase more than proportionally with increasing dosages; the time required to reach steady state increases with increasing daily dose. Dosage intervals of 8-12 h are sufficient to maintain plasma salicylate concentrations in the normal therapeutic anti-inflammatory concentration range [10].

Protein binding

Please refer to Aspirin for protein binding of salicylates.

Metabolism

Hydrolyzed to salicylic acid [11]. Salicylic acid elimination kinetics are dependent on drug concentration because of the limited capacity of two major biotransformation pathways: formation of salicyluric acid and of salicyl phenolic glucuronide.

Metabolism of this drug occurs mainly in the liver, like other salicylates [3].

Metabolism of salicylic acid occurs through glucuronide formation (to produce salicyluric acid), and salicyl phenolic glucuronide), conjugation with glycine (to produce salicyluric acid), and oxidation to form gentisic acid. The rate of formation of salicyl phenolic glucuronide and salicyluric acid are easily saturated at low salicylic acid concentrations and their formation can be described by Michaelis-Menten kinetics [3].

Route of elimination

Please refer to Aspirin for the route of elimination.

Half life

Mean half-life of 1.1 h [15].

Clearance

Please refer to Aspirin for more information.

Toxicity

Oral LD50 in the rat is 3000 mg/kg [13]

Adverse effects can be divided into several categories [4], [12]:

Eyes: irritation [12]

Skin: skin irritation [12]

Cardiovascular: rapid pulse, flushing [4]

Central Nervous System —blurred vision, dizziness [4]

Respiratory —shortness of breath or troubled breathing [4], irritation of respiratory system [12]

Genitourinary —difficult micturition, acute urinary retention [4]

Gastrointestinal —dry mouth, nausea/vomiting [4]

Overdosage may be managed by inducing emesis or gastric lavage. Slow intravenous administration of physostigmine in doses of 1 to 4 mg (0.5 to 1 mg in children) repeated as needed in 1-2 h to relieve severe antimuscarinic symptoms. Administration of small doses of diazepam to control excitement and seizures may be warranted. Artificial respiration with oxygen can be used if needed for respiratory depression. Adequate hydration is important, as well as symptomatic treatment, provided as necessary [4].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [PubMed:14592543]
  2. Ozaki H, Sugihara K, Tamura Y, Fujino C, Watanabe Y, Uramaru N, Sone T, Ohta S, Kitamura S: Hydrolytic metabolism of phenyl and benzyl salicylates, fragrances and flavoring agents in foods, by microsomes of rat and human tissues. Food Chem Toxicol. 2015 Dec;86:116-23. doi: 10.1016/j.fct.2015.08.024. Epub 2015 Aug 28. [PubMed:26321725]
  3. Needs CJ, Brooks PM: Clinical pharmacokinetics of the salicylates. Clin Pharmacokinet. 1985 Mar-Apr;10(2):164-77. doi: 10.2165/00003088-198510020-00004. [PubMed:3888490]
  4. Phenyl Salicylate [Link]
  5. Phenyl Salicylate [Link]
  6. Phenyl Salicylate, CHeBi [Link]
  7. HYOPHEN- methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate tablet [Link]
  8. Methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate [Link]
  9. Phenyl Salicylate, Norway RISK PROFILE [Link]
  10. The pharmacokinetics of salicylate [Link]
  11. A toxicologic and dermatologic assessment of salicylates when used as fragrance ingredients [Link]
  12. Santa Cruz SDS sheet, Phenyl Salicylate [Link]
  13. Phenyl Salicylate SDS [Link]
  14. Phenyl salicylate (T3D4905) [Link]
  15. Absorption, Biotransformation, and Pharmacokinetics of Salicylsalicylic Acid in Humans [Link]
  16. FDA Everything Added to Food Listing [Link]
  17. Molecular Targets of Aspirin and Cancer Prevention [Link]
External Links
Human Metabolome Database
HMDB0032018
KEGG Compound
C14163
PubChem Compound
8361
PubChem Substance
347827884
ChemSpider
8058
ChEBI
34918
ChEMBL
CHEMBL1339216
Wikipedia
Phenyl_salicylate
ATC Codes
G04BX12 — Phenyl salicylate
MSDS
Download (154 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral
CapsuleOral
Tablet, sugar coatedOral
LiquidOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)41-43MSDS
boiling point (°C)172-173MSDS
water solubilityinsoluble MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.216 mg/mLALOGPS
logP3.58ALOGPS
logP3.98ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity59.84 m3·mol-1ChemAxon
Polarizability21.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00di-4900000000-fcc0d5e766dfb52cf2d9
Mass Spectrum (Electron Ionization)MSsplash10-00di-4910000000-5d4e08b10364ff3dc525
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0390000000-99da4cb99d88023844ad
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-2950000000-37c2025a458ede4ba4d2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-9300000000-c7779524725bb16e6bb0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1090000000-e53ec6eaf869f0bc1d30
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-3190000000-157a064fd6d6fdb02acc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-6dc8ce8b6b3c630a3003
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Depsides and depsidones
Sub Class
Not Available
Direct Parent
Depsides and depsidones
Alternative Parents
o-Hydroxybenzoic acid esters / Salicylic acid and derivatives / Phenol esters / Phenoxy compounds / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Carboxylic acid esters / Monocarboxylic acids and derivatives
show 3 more
Substituents
Depside backbone / O-hydroxybenzoic acid ester / Benzoate ester / Salicylic acid or derivatives / Phenol ester / Benzoic acid or derivatives / Phenoxy compound / Benzoyl / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, salicylates, benzoate ester (CHEBI:34918)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Molecular Targets of Aspirin and Cancer Prevention [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Molecular Targets of Aspirin and Cancer Prevention [Link]

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 07:06