Glycol salicylate
Identification
- Summary
Glycol salicylate is a salicylate used to treat mild to moderate muscle pain.
- Generic Name
- Glycol salicylate
- DrugBank Accession Number
- DB11323
- Background
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
- 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
- Indication
This drug is only recommended for topical usages for the relief of muscular and rheumatic pain in human and animals 10.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Back pain lower back Combination Product in combination with: Synthetic camphor (DB14156), alpha-Tocopherol acetate (DB14003), Levomenthol (DB00825) ••• ••• ••••• Used in combination to treat Bruises Combination Product in combination with: alpha-Tocopherol acetate (DB14003), Levomenthol (DB00825), Synthetic camphor (DB14156) ••• ••• ••••• Used in combination to treat Chilblains Combination Product in combination with: Levomenthol (DB00825), alpha-Tocopherol acetate (DB14003), Synthetic camphor (DB14156) ••• ••• ••••• Used in combination to treat Joint pain Combination Product in combination with: Levomenthol (DB00825), alpha-Tocopherol acetate (DB14003), Synthetic camphor (DB14156) ••• ••• ••••• Used in combination to treat Pain caused by fracture bone Combination Product in combination with: Synthetic camphor (DB14156), alpha-Tocopherol acetate (DB14003), Levomenthol (DB00825) ••• ••• ••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism AProstaglandin G/H synthase 1 antagonistHumans AProstaglandin G/H synthase 2 antagonistHumans - 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
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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.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of bleeding and hemorrhage can be increased when Glycol salicylate is combined with Abciximab. Acebutolol Glycol salicylate may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Glycol salicylate. Acemetacin The risk or severity of adverse effects can be increased when Glycol salicylate is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Glycol salicylate is combined with Acenocoumarol. - 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.
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AMMELTZ YOKO YOKO Glycol salicylate (2.5 g/100ml) + Benzyl nicotinate (10 mg/100ml) + Chlorpheniramine maleate (100 mg/100ml) + Levomenthol (3 g/100ml) + Nonivamide (12 mg/100ml) Liquid Topical KOBAYASHI Healthcare (Malaysia) Sdn. Bhd. 2020-09-08 Not applicable Malaysia Counterpain Patch Glycol salicylate (1.4 % w/w) + Levomenthol (4.9 % w/w) + Synthetic camphor (0.9 % w/w) + alpha-Tocopherol acetate (2 % w/w) Patch Transdermal HOE PHARMACEUTICALS SDN. BHD. 2020-09-08 Not applicable Malaysia Counterpain Patch Hot Glycol salicylate (2 % w/w) + Levomenthol (1 % w/w) + Nonivamide (0.013 % w/w) + alpha-Tocopherol acetate (0.8 % w/w) Patch Transdermal HOE PHARMACEUTICALS SDN. BHD. 2020-09-08 Not applicable Malaysia Deep Heat Sports Pain Relief Spray Glycol salicylate (5 % w/w) + Ethyl salicylate (5 % w/w) + Methyl nicotinate (1.6 % w/w) + Methyl salicylate (1 % w/w) Aerosol, spray Topical ROHTO-MENTHOLATUM (M) SDN. BHD. 2020-09-08 2022-02-08 Malaysia Etrat - Gel Glycol salicylate (5 g) + Heparin sodium (5000 IU) + Levomenthol (0.5 g) Gel Topical Glenwood Gmb H Pharmazeutische Erzeugnisse 1973-12-13 Not applicable Austria
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)
- Affected organisms
- Humans and other mammals
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
- 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. [Article]
- Pearlman BL, Gambhir R: Salicylate intoxication: a clinical review. Postgrad Med. 2009 Jul;121(4):162-8. doi: 10.3810/pgm.2009.07.2041. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Taniguchi Y, Deguchi Y, Saita M, Noda K: [Antinociceptive effects of counterirritants]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):433-46. [Article]
- Levy G: Clinical pharmacokinetics of salicylates: a re-assessment. Br J Clin Pharmacol. 1980 Oct;10 Suppl 2:285S-290S. [Article]
- Glycol Salicylate, PubChem [Link]
- Skin Irritation and Pharmacokinetics of Glycol Salicylate Transdermal Patches in Sprague–Dawley Rats [Link]
- Topical penetration of commercial salicylate esters and salts using human isolated skin and clinical microdialysis studies [Link]
- FAMILY CARE THERA FLEX- menthol glycol salicylate nonivamide tocopherol acetate patch [Link]
- SALONPAS [Link]
- Salicylates, PubMED [Link]
- Aspirin and Other Salicylate Poisoning [Link]
- Glycol Salicylate [Link]
- Glycol Salicylate [Link]
- Counter-Irritant [Link]
- Counterirritants [Link]
- Clinical Pharmacokinetics of the Salicylates [Link]
- Clinical Review: CLINICAL REVIEW [File]
- External Links
- PubChem Compound
- 6880
- PubChem Substance
- 347827966
- ChemSpider
- 6616
- 26051
- ChEBI
- 86541
- ChEMBL
- CHEMBL173562
- ZINC
- ZINC000001698306
- MSDS
- Download (162 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical Patch Transdermal Aerosol, spray Topical Gel Topical Ointment Topical Patch Topical Emulsion Topical Plaster Topical Aerosol Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 25 MSDS boiling point (°C) 166 MSDS water solubility 13.1 g/L MSDS - Predicted Properties
Property Value Source Water Solubility 3.8 mg/mL ALOGPS logP 0.89 ALOGPS logP 1.63 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 9.72 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.76 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 46.36 m3·mol-1 Chemaxon Polarizability 18.04 Å3 Chemaxon Number of Rings 1 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
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-3900000000-0626f37f1396c4fa1df5 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9200000000-dca4cbbdd9c4d4de48a5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-5900000000-1917af8f2abc9b4760e9 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-0098bf51a003828b0094 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4j-9700000000-7ac1912610d82a5a8190 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-0abe6eba21297790c209 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 143.9682695 predictedDarkChem Lite v0.1.0 [M-H]- 144.0375695 predictedDarkChem Lite v0.1.0 [M-H]- 134.18108 predictedDeepCCS 1.0 (2019) [M+H]+ 142.7995695 predictedDarkChem Lite v0.1.0 [M+H]+ 143.5451695 predictedDarkChem Lite v0.1.0 [M+H]+ 137.62282 predictedDeepCCS 1.0 (2019) [M+Na]+ 142.9725695 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.9655695 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.59755 predictedDeepCCS 1.0 (2019)
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
- Levy G: Clinical pharmacokinetics of salicylates: a re-assessment. Br J Clin Pharmacol. 1980 Oct;10 Suppl 2:285S-290S. [Article]
- 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
- Levy G: Clinical pharmacokinetics of salicylates: a re-assessment. Br J Clin Pharmacol. 1980 Oct;10 Suppl 2:285S-290S. [Article]
Drug created at December 03, 2015 16:52 / Updated at February 21, 2021 18:53