Glycol salicylate

Identification

Name
Glycol salicylate
Accession Number
DB11323
Description

Glycol salicylate, also known as 2-hydroxyethyl salicylate, is a benzoate ester formed from the condensation of the carboxy group of salicylic acid with one of the hydroxy groups of ethylene glycol. It is found as an active ingredient and topical analgesic in patches used to provide relief for mild to moderate muscle and joint pain 9.

This drug belongs to the salicylate group of drugs, which are used as analgesic agents for the treatment of mild to moderate pain 14.

Glycol salicylate (GS), composed of salicylic acid (SA) and ethylene glycol, is a non-steroidal anti-inflammatory drug 10.

This ingredient is an important component of many topical creams and sprays for the relief of aches, pains, and stiffness of the muscles, joints, and tendons 17.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 182.175
Monoisotopic: 182.057908802
Chemical Formula
C9H10O4
Synonyms
  • 2-hydroxybenzoic acid 2-hydroxyethyl ester
  • 2-hydroxyethyl 2-oxidanylbenzoate
  • 2-hydroxyethyl salicylate
  • Ethylene glycol monosalicylate
  • Ethylene glycol salicylate
  • Glycol salicylate

Pharmacology

Pharmacology
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Indication

This drug is only recommended for topical usages for the relief of muscular and rheumatic pain in human and animals 10.

Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Temporarily relieves minor to moderate aches and pains 12. Works with ingredients such as menthol, which has counter-irritant properties 13. Counter-irritants are externally applied, and lead to irritation or mild inflammation of the skin to relieve pain in muscles or joints by reducing inflammation in deeper adjacent structures 19. Counter-irritants relieve pain by disrupting the brain from receiving pain signals resulting from conditions such as osteoarthritis (OA) or injuries such as sprains or strains. These agents may cause vasodilatation or skin irritation, leading to a false sensation of heat or warmth 18.

Mechanism of action

Similar to other salicylates. Salicylates and other analgesics and anti-inflammatory drugs, particularly the non-steroidal anti-inflammatory drugs (NSAID) mainly used in rheumatology, inhibit cyclooxygenase, therefore reducing prostaglandin synthesis 1.

TargetActionsOrganism
AProstaglandin G/H synthase 1
antagonist
Humans
AProstaglandin G/H synthase 2
antagonist
Humans
Absorption

Salicylate absorption follows first-order kinetics with an absorption half-life ranging from 5 to 16 minutes 20.

Volume of distribution
Not Available
Protein binding

The plasma protein binding of salicylic acid is concentration-dependent and subject to pronounced interindividual differences 8.

Metabolism

The metabolism of glycol salicylate is similar to that of Aspirin at other salicylates 20.

Metabolism of salicylic acid occurs through glucuronide formation (to produce salicyl acyl glucuronide and salicyl phenolic glucuronide), conjugation with glycine (to produce salicyluric acid), and oxidation to gentisic acid. The rate of formation of salicyl phenolic glucuronide and salicyluric acid are readily saturated at low salicylic acid concentrations and their formation is described by Michaelis-Menten kinetics. The larger the dose administered, the longer it will take to reach steady-state concentrations of salicylates. There is also evidence that enzyme induction of salicyluric acid formation occurs during the metabolism of salicylates 20.

Route of elimination

Salicylates are generally excreted 20.

Half-life

The serum half-life of Aspirin, a similar salicylate, is 20 min 20.

Clearance
Not Available
Adverse Effects
Medicalerrors
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Toxicity

Acute ingestion of > 150 mg/kg of salicylates may result in severe toxicity. Salicylate tablets may form stomach bezoars, prolonging absorption of the drug and toxicity. Chronic toxicity can occur after several days or more of high therapeutic doses; it is common, often undiagnosed, and often more serious than acute toxicity. Chronic toxicity is likely to occur in elderly patients 15.

Treatment for salicylate poisoning consists of activated charcoal and alkaline diuresis with extra KCl 15.

Unless contraindicated (eg, by altered mental status), activated charcoal is administered as soon as possible and, if bowel sounds are active and there is adequate gastrointestinal motility, may be repeated every 4 hours until charcoal appears in the stool 15.

After volume and electrolyte abnormalities are corrected and maintained, alkaline diuresis can be used to increase urine pH, ideally to ≥ 8. Alkaline diuresis is advised for patients with any symptoms of poisoning and should not be delayed until salicylate levels are determined. This process is usually safe and greatly increases the rate of salicylate excretion. Because hypokalemia can interfere with alkaline diuresis, patients are often given a solution composed of 1 L of 5% D/W, 3 50-mEq ampules of NaHCO3, and 40 mEq of KCl at 1.5 to 2 times the maintenance IV fluid rate. Serum potassium levels are monitored. Due to the fact that fluid overload can lead to the occurrence of pulmonary edema, patients are monitored for respiratory findings 15.

Drugs that increase urinary HCO3 (eg, acetazolamide) must be avoided because they worsen metabolic acidosis and decrease blood pH. Drugs that decrease respiratory drive should be avoided when possible because they may impair hyperventilation and respiratory alkalosis, decreasing blood pH 16.

Affected organisms
  • Humans and other mammals
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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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Family Care Thera FlexGlycol salicylate (4.66 mg/100mg) + Levomenthol (6.53 mg/100mg) + Nonivamide (.01 mg/100mg) + alpha-Tocopherol acetate (.93 mg/100mg)PatchTopicalUnited Exchange Corporation2013-11-15Not applicableUS flag
Jupiter Pain PatchGlycol salicylate (1.0 %) + Camphor (1.0 %) + Capsaicin (0.03 %)PatchTopicalJupiter Consumer Products Ltd.Not applicableNot applicableCanada flag
MidalganGlycol salicylate (10 g) + Capsicum (100 mg) + Histamine dihydrochloride (100 mg) + Methyl nicotinate (1 g)OintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1948-12-311999-09-17Canada flag
New AmmeltzGlycol salicylate (25 mg) + Levomenthol (30 mg)LiquidTopicalClassical Remedia LtdNot applicableNot applicableCanada flag
Nopen CoolGlycol salicylate (35 mg/1) + Levomenthol (35 mg/1)PatchTransdermalJW HOLDINGS CORPORATION2018-08-17Not applicableUS flag
Nopen HotGlycol salicylate (35 mg/1) + Levomenthol (35 mg/1)PatchTransdermalJW HOLDINGS CORPORATION2018-08-172019-12-31US flag
Salonpas - Pls TopGlycol salicylate (.9 %) + Camphor (1.2 %) + Levomenthol (5.7 %) + Methyl salicylate (6.2 %) + Thymol (.8 %)PlasterTopicalHisamitsu Pharmaceutical Co., Inc.1995-08-032003-11-04Canada flag
Salonpas Gel-patchGlycol salicylate (1.25 g) + Camphor (0.3 g) + Levomenthol (1.00 g)PlasterTopicalHisamitsu Pharmaceutical Co., Inc.2002-02-01Not applicableCanada flag
Tokuhon Medicated PlasterGlycol salicylate (1.62 %) + Camphor (0.97 %) + Levomenthol (5.67 %) + Methyl salicylate (6.05 %)PlasterTopicalEastland Drug Co. Ltd.1998-02-272011-08-24Canada flag
Ultraplast Analgesic SprayGlycol salicylate (4.8 %) + Ethyl salicylate (4.8 %) + Methyl nicotinate (1.6 %) + Methyl salicylate (.96 %)AerosolTopicalWallace, Cameron and Company Ltd.1985-12-312000-07-31Canada flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
o-Hydroxybenzoic acid esters
Alternative Parents
Salicylic acid and derivatives / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Carboxylic acid esters / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Aromatic homomonocyclic compound / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / O-hydroxybenzoic acid ester
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, salicylates, primary alcohol, benzoate ester (CHEBI:86541)

Chemical Identifiers

UNII
3I1VBB7AXH
CAS number
87-28-5
InChI Key
LVYLCBNXHHHPSB-UHFFFAOYSA-N
InChI
InChI=1S/C9H10O4/c10-5-6-13-9(12)7-3-1-2-4-8(7)11/h1-4,10-11H,5-6H2
IUPAC Name
2-hydroxyethyl 2-hydroxybenzoate
SMILES
OCCOC(=O)C1=CC=CC=C1O

References

General References
  1. Baenkler HW: Salicylate intolerance: pathophysiology, clinical spectrum, diagnosis and treatment. Dtsch Arztebl Int. 2008 Feb;105(8):137-42. doi: 10.3238/arztebl.2008.0137. Epub 2008 Feb 22. [PubMed:19633779]
  2. Pearlman BL, Gambhir R: Salicylate intoxication: a clinical review. Postgrad Med. 2009 Jul;121(4):162-8. doi: 10.3810/pgm.2009.07.2041. [PubMed:19641282]
  3. Paterson J, Baxter G, Lawrence J, Duthie G: Is there a role for dietary salicylates in health? Proc Nutr Soc. 2006 Feb;65(1):93-6. [PubMed:16441948]
  4. Chyka PA, Erdman AR, Christianson G, Wax PM, Booze LL, Manoguerra AS, Caravati EM, Nelson LS, Olson KR, Cobaugh DJ, Scharman EJ, Woolf AD, Troutman WG: Salicylate poisoning: an evidence-based consensus guideline for out-of-hospital management. Clin Toxicol (Phila). 2007;45(2):95-131. doi: 10.1080/15563650600907140. [PubMed:17364628]
  5. Durnas C, Cusack BJ: Salicylate intoxication in the elderly. Recognition and recommendations on how to prevent it. Drugs Aging. 1992 Jan-Feb;2(1):20-34. [PubMed:1554971]
  6. Cross SE, Anderson C, Roberts MS: Topical penetration of commercial salicylate esters and salts using human isolated skin and clinical microdialysis studies. Br J Clin Pharmacol. 1998 Jul;46(1):29-35. [PubMed:9690946]
  7. Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [PubMed:7851817]
  8. Levy G: Clinical pharmacokinetics of salicylates: a re-assessment. Br J Clin Pharmacol. 1980 Oct;10 Suppl 2:285S-290S. [PubMed:7437270]
  9. Glycol Salicylate, PubChem [Link]
  10. Skin Irritation and Pharmacokinetics of Glycol Salicylate Transdermal Patches in Sprague–Dawley Rats [Link]
  11. Topical penetration of commercial salicylate esters and salts using human isolated skin and clinical microdialysis studies [Link]
  12. FAMILY CARE THERA FLEX- menthol glycol salicylate nonivamide tocopherol acetate patch [Link]
  13. SALONPAS [Link]
  14. Salicylates, PubMED [Link]
  15. Aspirin and Other Salicylate Poisoning [Link]
  16. Glycol Salicylate [Link]
  17. Glycol Salicylate [Link]
  18. Counter-Irritant [Link]
  19. Counterirritants [Link]
  20. Clinical Pharmacokinetics of the Salicylates [Link]
  21. Clinical Review: CLINICAL REVIEW [File]
PubChem Compound
6880
PubChem Substance
347827966
ChemSpider
6616
RxNav
26051
ChEBI
86541
ChEMBL
CHEMBL173562
ZINC
ZINC000001698306
MSDS
Download (162 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidTopical3 g/100ml
PatchTransdermal1.4 % w/w
PatchTransdermal2 % w/w
Aerosol, sprayTopical5 % w/w
GelTopical5000 IU
PatchTopical
OintmentTopical
LiquidTopical
LiquidTopical2500 mg
LiquidTopical10 %w/w
LiquidTopical2.5 %
PatchTransdermal
PatchTopical0.5 %
EmulsionTopical0.1 g/100ml
PatchTransdermal33 mg
PatchTopical7 %
PatchTopical2 %
PlasterTopical
AerosolTopical
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)25MSDS
boiling point (°C)166MSDS
water solubility13.1 g/LMSDS
Predicted Properties
PropertyValueSource
Water Solubility3.8 mg/mLALOGPS
logP0.89ALOGPS
logP1.63ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.72ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.36 m3·mol-1ChemAxon
Polarizability18.04 Å3ChemAxon
Number of Rings1ChemAxon
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. Levy G: Clinical pharmacokinetics of salicylates: a re-assessment. Br J Clin Pharmacol. 1980 Oct;10 Suppl 2:285S-290S. [PubMed:7437270]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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. Levy G: Clinical pharmacokinetics of salicylates: a re-assessment. Br J Clin Pharmacol. 1980 Oct;10 Suppl 2:285S-290S. [PubMed:7437270]

Drug created on December 03, 2015 16:52 / Updated on February 21, 2021 18:53