Phenyl salicylate

Identification

Brand Names
Hyophen, Phosphasal, Urelle, Uribel, Urimar Reformulated Oct 2013, Urin DS, Ustell
Generic Name
Phenyl salicylate
DrugBank Accession Number
DB11071
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 214.2167
Monoisotopic: 214.062994186
Chemical Formula
C13H10O3
Synonyms
  • Salol
External IDs
  • FEMA NO. 3960

Pharmacology

Indication

Pain and fever 6.

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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
Humans
UProstaglandin G/H synthase 2
antagonist
Humans
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.

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ยาธาตุน้ำขาวSuspension300 mg/15mlบริษัท เอช.เค.ฟาร์มาซูติคอล จำกัด2015-11-04Not applicableThailand flag
ยาธาตุน้ำขาว เอส.พี.Emulsion300 mg/15mlห้างหุ้นส่วนจำกัด สุพงษ์เภสัช1993-06-23Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Watkins SettelzPhenyl salicylate (29 mg / 28.4 mL) + Bismuth subsalicylate (236 mg / 28.4 mL) + Pectin (274 mg / 28.4 mL)LiquidOralWatkins Incorporated1954-12-312011-08-04Canada flag
ซาน ซิออง หวันPhenyl salicylate (0.02 g) + Belladonna (900 mcg) + Cinnamon (0.04 g) + Clove (0.03 g) + Glycyrrhiza glabra (0.08 g) + Levomenthol (0.005 g) + Wood creosote (0.015 ml)Pillบริษัท แมคโครฟาร์ จำกัด2016-06-07Not applicableThailand flag
ซิก้าซาลอล-บีอาร์Phenyl salicylate (260 MG/15ML) + Levomenthol (26 MG/15ML)SuspensionOralบริษัท บางกอกแล็ป แอนด์ คอสเมติค จำกัด จำกัด2007-07-202019-10-21Thailand flag
มิกซ์เจอร์ ซาโลล เอท เมนทอลPhenyl salicylate (225 MG/15ML) + Levomenthol (45 MG/15ML)SuspensionOralบริษัท บุคคโล เทรดดิ้ง จำกัด จำกัด1990-10-22Not applicableThailand flag
ยาธาตุน้ำขาวPhenyl salicylate (300 MG/15ML) + Levomenthol (30 MG/15ML)SuspensionOralบริษัท วิทยาศรม จำกัด1985-09-27Not applicableThailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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 flag
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 flag
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 flag
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 flag

Categories

ATC Codes
G04BX12 — Phenyl salicylate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Depside backbone
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, salicylates, benzoate ester (CHEBI:34918)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
28A37T47QO
CAS number
118-55-8
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

References

General References
  1. Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [Article]
  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. [Article]
  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. [Article]
  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]
Human Metabolome Database
HMDB0032018
KEGG Compound
C14163
PubChem Compound
8361
PubChem Substance
347827884
ChemSpider
8058
RxNav
36122
ChEBI
34918
ChEMBL
CHEMBL1339216
ZINC
ZINC000000038545
Wikipedia
Phenyl_salicylate
MSDS
Download (154 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
CapsuleOral
Tablet, coatedOral
Tablet, sugar coatedOral
LiquidOral
EmulsionOral
Suspension300 mg/15ml
SuspensionOral
Emulsion300 mg/15ml
Pill
Tablet
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-MSsplash10-00di-9600000000-6e2ea24d5a7e7f20d7f9
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/MSsplash10-00di-2900000000-877d855eb0e31561d592
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-1a3f3998b56afdb9124e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-4910000000-ea7b2739a78ae0faf6c5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-bc0c8e819b53816f2f9f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-9300000000-a17db84b33da5df8a6cb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fkc-9300000000-5924c0d423e0044449d5
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-155.0661239
predicted
DarkChem Lite v0.1.0
[M-H]-155.1766239
predicted
DarkChem Lite v0.1.0
[M-H]-155.0768239
predicted
DarkChem Lite v0.1.0
[M-H]-154.8884239
predicted
DarkChem Lite v0.1.0
[M-H]-144.95114
predicted
DeepCCS 1.0 (2019)
[M+H]+155.7556239
predicted
DarkChem Lite v0.1.0
[M+H]+155.5321239
predicted
DarkChem Lite v0.1.0
[M+H]+156.1025239
predicted
DarkChem Lite v0.1.0
[M+H]+155.8174239
predicted
DarkChem Lite v0.1.0
[M+H]+147.34671
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.0707239
predicted
DarkChem Lite v0.1.0
[M+Na]+155.0795239
predicted
DarkChem Lite v0.1.0
[M+Na]+155.2788239
predicted
DarkChem Lite v0.1.0
[M+Na]+154.9239239
predicted
DarkChem Lite v0.1.0
[M+Na]+153.57227
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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
Humans
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 at December 03, 2015 16:51 / Updated at February 13, 2021 10:52