Explore a selection of our essential drug information below, or:
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
Structure for Phenyl salicylate (DB11071)
- 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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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.
Target Actions Organism UProstaglandin G/H synthase 1 antagonistHumans UProstaglandin G/H synthase 2 antagonistHumans - 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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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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ยาธาตุน้ำขาว Suspension 300 mg/15ml บริษัท เอช.เค.ฟาร์มาซูติคอล จำกัด 2015-11-04 Not applicable Thailand 
ยาธาตุน้ำขาว เอส.พี. Emulsion 300 mg/15ml ห้างหุ้นส่วนจำกัด สุพงษ์เภสัช 1993-06-23 Not applicable Thailand - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Watkins Settelz Phenyl salicylate (29 mg / 28.4 mL) + Bismuth subsalicylate (236 mg / 28.4 mL) + Pectin (274 mg / 28.4 mL) Liquid Oral Watkins Incorporated 1954-12-31 2011-08-04 Canada 
ซาน ซิออง หวัน Phenyl 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) Pill บริษัท แมคโครฟาร์ จำกัด 2016-06-07 Not applicable Thailand ซิก้าซาลอล-บีอาร์ Phenyl salicylate (260 MG/15ML) + Levomenthol (26 MG/15ML) Suspension Oral บริษัท บางกอกแล็ป แอนด์ คอสเมติค จำกัด จำกัด 2007-07-20 2019-10-21 Thailand มิกซ์เจอร์ ซาโลล เอท เมนทอล Phenyl salicylate (225 MG/15ML) + Levomenthol (45 MG/15ML) Suspension Oral บริษัท บุคคโล เทรดดิ้ง จำกัด จำกัด 1990-10-22 Not applicable Thailand ยาธาตุน้ำขาว Phenyl salicylate (225 MG/15ML) + Levomenthol (22.5 MG/15ML) Emulsion Oral บริษัท บี.เอ็ล.ฮั้ว จำกัด จำกัด 1984-05-27 Not applicable Thailand - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Azuphen Mb Phenyl 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) Capsule Oral Burel Pharmaceuticals, Llc 2015-09-28 2016-11-01 US 
Darcalma Phenyl 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) Tablet Oral River's Edge Pharmaceuticals, LLC 2008-12-22 2011-07-31 US Darcalma Phenyl 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) Tablet Oral Kylemore Pharmaceuticals, LLC 2009-12-01 2009-12-02 US Darpaz Phenyl 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) Tablet Oral River's Edge Pharmaceuticals, LLC 2008-12-01 2011-05-31 US Hyolev Mb Phenyl 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) Tablet Oral Burel Pharmaceuticals, Llc 2015-06-26 2016-11-01 US
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
- Vane JR, Botting RM: The mechanism of action of aspirin. Thromb Res. 2003 Jun 15;110(5-6):255-8. [Article]
- 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]
- 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]
- Phenyl Salicylate [Link]
- Phenyl Salicylate [Link]
- Phenyl Salicylate, CHeBi [Link]
- HYOPHEN- methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate tablet [Link]
- Methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate [Link]
- Phenyl Salicylate, Norway RISK PROFILE [Link]
- The pharmacokinetics of salicylate [Link]
- A toxicologic and dermatologic assessment of salicylates when used as fragrance ingredients [Link]
- Santa Cruz SDS sheet, Phenyl Salicylate [Link]
- Phenyl Salicylate SDS [Link]
- Phenyl salicylate (T3D4905) [Link]
- Absorption, Biotransformation, and Pharmacokinetics of Salicylsalicylic Acid in Humans [Link]
- FDA Everything Added to Food Listing [Link]
- 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
- 36122
- ChEBI
- 34918
- ChEMBL
- CHEMBL1339216
- ZINC
- ZINC000000038545
- Wikipedia
- Phenyl_salicylate
- MSDS
- Download (154 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Capsule Oral Tablet, coated Oral Tablet, sugar coated Oral Liquid Oral Emulsion Oral Suspension 300 mg/15ml Suspension Oral Emulsion 300 mg/15ml Pill Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 41-43 MSDS boiling point (°C) 172-173 MSDS water solubility insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.216 mg/mL ALOGPS logP 3.58 ALOGPS logP 3.98 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 9.67 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 59.84 m3·mol-1 Chemaxon Polarizability 21.96 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.0661239 predictedDarkChem Lite v0.1.0 [M-H]- 155.1766239 predictedDarkChem Lite v0.1.0 [M-H]- 155.0768239 predictedDarkChem Lite v0.1.0 [M-H]- 154.8884239 predictedDarkChem Lite v0.1.0 [M-H]- 144.95114 predictedDeepCCS 1.0 (2019) [M+H]+ 155.7556239 predictedDarkChem Lite v0.1.0 [M+H]+ 155.5321239 predictedDarkChem Lite v0.1.0 [M+H]+ 156.1025239 predictedDarkChem Lite v0.1.0 [M+H]+ 155.8174239 predictedDarkChem Lite v0.1.0 [M+H]+ 147.34671 predictedDeepCCS 1.0 (2019) [M+Na]+ 155.0707239 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.0795239 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.2788239 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.9239239 predictedDarkChem Lite v0.1.0 [M+Na]+ 153.57227 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- Heme binding
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Molecular Targets of Aspirin and Cancer Prevention [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
- Specific Function
- Enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Molecular Targets of Aspirin and Cancer Prevention [Link]
Drug created at December 03, 2015 16:51 / Updated at February 13, 2021 10:52