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Identification
- Summary
Trolamine salicylate is a medication used to relieve minor aches and pains of the muscles and joints.
- Brand Names
- Asper-flex, Aspercreme, Mobisyl, Myoflex, Sportscreme
- Generic Name
- Trolamine salicylate
- DrugBank Accession Number
- DB11079
- Background
Trolamine salicylate is an organic compound or a salt formed between triethanolamine and salicylic acid. Triethanolamine neutralizes the acidity of the salicylic acid. It is a topical analgesic used for temporary relief of minor pain associated with arthritis, simple backache, muscle strains, sprains, and bruises. Unlike other topical analgesics, trolamine salicylate has no distinct odor which improves patient acceptability 2. It also displays low systemic absorption upon dermal or topical administration 3 and has low skin irritant properties 4. As with other salicylates, trolamine salicylate is an inhibitor of cyclo-oxygenase (COX) enzymes with no reported selectivity towards a specific enzyme isoform. Trolamine salicylate serves as an active ingredient in topical over-the-counter products for temporary management of mild to moderate muscular and joint pains.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Trolamine salicylate (DB11079)
- Weight
- Average: 287.312
Monoisotopic: 287.1368874 - Chemical Formula
- C13H21NO6
- Synonyms
- Trolamine salicylate
Pharmacology
- Indication
Indicated for the temporary relief of aches, and pains of muscles and joints associated with backache, lumbago, strains, bruises, sprains and arthritic or rheumatic pain, pain of tendons and ligaments 6.
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Trolamine salicylate is a salicylate that inhibits cyclo-oxygenase (COX) enzymes responsible for generating pro-inflammatory factors such as to induce pain and inflammation. It is thought to mediate its analgesic effect through inhibition of COX-2 enzyme, which is an induced enzyme responsible for inflammatory responses and pain in muscle and joint disorders. By inhibiting fatty acid COX enzyme, trolamine salicylate inhibits the production of prostaglandins and thromboxanes in inflammatory cells involved in generating pain and inflammation 5. It thereby works to temporarily reduce mild to moderate pain. In subjects with muscle soreness from exercise, administration of topical trolamine salicylate was associated with reduced duration and severity of muscule soreness compared to placebo 2. In subjects with osteoarthritis in hands, trolamine salicylate cream was shown to be effective in achieving temporary relief of minor pain and stiffness 1.
- Mechanism of action
Inflammation and tissue damage in different conditions including arthritis, bursitis, joint disorder, bruises, and strains or sprains of muscle origin, induce mild to moderate pain and are associated with increase prostaglandin synthesis 5. This is thought to be a result of COX-2 enzyme induction. COX-2 is induced in inflammatory cells in case of cell injury, infection or activation from inflammatory cytokines such as interleukin (IL)-1 and tumor necrosis factor (TNF)-α. Upon activation, COX-2 produces prostanoid mediators of inflammation such as prostaglandins and thromboxanes 5. Trolamine salicylate mediates its analgesic effect by inhibiting the production of inflammatory mediators that sensitize nociceptive nerve endings and generate pain 5.
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans - Absorption
Following topical administration of 10% trolamine salicylate in healthy volunteers, salicylic acid could not be detected in serum indicating low systemic absorption 3.
- Volume of distribution
Topical administration of 1 gram of 10% trolamine salicylate in abdominal rat skin resulted in an approximate extravascular volume of distribution (V/F) of 24.0 mL 4.
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Following topical administration of 10% trolamine salicylate in healthy volunteers, urinary recovery of total salicylate during the first 24 hours was 6.9 mg (p < 0.05), which is 1.4% of total dose 3.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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It is hazardous in case of ingestion MSDS. The carcinogenicity, mutagenicity and effects on reproductive fertility of trolamine salicylate have not been reported.
- 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 can be increased when Trolamine salicylate is combined with Abciximab. Acarbose Trolamine salicylate may increase the hypoglycemic activities of Acarbose. Aceclofenac The therapeutic efficacy of Trolamine salicylate can be decreased when used in combination with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Trolamine salicylate is combined with Acemetacin. Acenocoumarol Trolamine salicylate may increase the anticoagulant activities of 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.- Active Moieties
Name Kind UNII CAS InChI Key Salicylic acid salt O414PZ4LPZ 69-72-7 YGSDEFSMJLZEOE-UHFFFAOYSA-N Trolamine salt 9O3K93S3TK 102-71-6 GSEJCLTVZPLZKY-UHFFFAOYSA-N - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abr 90 Spray 10 g/100mL Topical Northwest Cosmetic Laboratories LLC 2000-11-01 2010-06-01 US 
Abr 90 Spray 10 g/100mL Topical ABR Medical, Inc. 2000-11-01 2014-06-04 US Actiflex Pain Relief Rub Cream 10 % Topical Pendopharm Division Of Pharmascience Inc 2003-01-20 2011-09-30 Canada 
Alcis Daily Relief Pain Relief Cream 10 g/100mL Topical Alcis Topical, Inc. 2009-03-09 Not applicable US Alcis Topical Pain Relief Cream Cream 10 % w/w Topical Alcis Health Inc. Not applicable Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Arthritis Extra Strength Roll-ON Lotion Trolamine salicylate (10 % w/w) + Capsaicin (0.035 % w/w) + Levomenthol (1.25 % w/w) Lotion Topical Church & Dwight Canada Corp 2008-09-15 2019-10-23 Canada Arthritis Pain Relief Trolamine salicylate (10 % w/w) + Capsaicin (0.035 % w/w) + Levomenthol (1.25 % w/w) Lotion Topical Church & Dwight Canada Corp 2019-10-28 Not applicable Canada Arthur Itis Cream Trolamine salicylate (10 %) + Capsaicin (0.025 %) Cream Topical Nabtech Pharma Inc. 1997-09-26 2005-09-20 Canada Ease Pain Away Analgesic Lotion Trolamine salicylate (10 %) + Levomenthol (1.25 %) Lotion Topical Rmc Group Inc. 1994-12-31 1999-11-23 Canada ELF Flawless Finish Foundation SPF 15 Oil Free Trolamine salicylate (2 g/100g) + Titanium dioxide (5.5 g/100g) Cream Topical J. A. Cosmetics U.S. INC 2011-10-03 2017-12-31 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Permavan External Patch Trolamine salicylate (10 g/100g) + Dextromethorphan hydrobromide monohydrate (4 g/100g) + Lidocaine (4 g/100g) Patch Topical Home Aide Diganostics, Inc. 2015-03-09 Not applicable US
Categories
- Drug Categories
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Benzene Derivatives
- Benzoates
- Hydroxy Acids
- Hydroxybenzoates
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Phenols
- Salicylates
- Sunscreen Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- 1,2-aminoalcohols
- Alternative Parents
- Trialkylamines / Monocarboxylic acids and derivatives / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 1,2-aminoalcohol / Alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxygen compound / Organooxygen compound / Organopnictogen compound / Primary alcohol / Tertiary aliphatic amine
- Molecular Framework
- Not Available
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- H8O4040BHD
- CAS number
- 2174-16-5
- InChI Key
- UEVAMYPIMMOEFW-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H6O3.C6H15NO3/c8-6-4-2-1-3-5(6)7(9)10;8-4-1-7(2-5-9)3-6-10/h1-4,8H,(H,9,10);8-10H,1-6H2
- IUPAC Name
- 2-[bis(2-hydroxyethyl)amino]ethan-1-ol; 2-hydroxybenzoic acid
- SMILES
- OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O
References
- General References
- Rothacker DQ, Lee I, Littlejohn TW 3rd: Effectiveness of a single topical application of 10|x% trolamine salicylate cream in the symptomatic treatment of osteoarthritis. J Clin Rheumatol. 1998 Feb;4(1):6-12. [Article]
- Hill DW, Richardson JD: Effectiveness of 10% trolamine salicylate cream on muscular soreness induced by a reproducible program of weight training. J Orthop Sports Phys Ther. 1989;11(1):19-23. [Article]
- Morra P, Bartle WR, Walker SE, Lee SN, Bowles SK, Reeves RA: Serum concentrations of salicylic acid following topically applied salicylate derivatives. Ann Pharmacother. 1996 Sep;30(9):935-40. doi: 10.1177/106002809603000903. [Article]
- Sajjadi P, Khodayar MJ, Sharif Makhmalzadeh B, Rezaee S: Percutaneous absorption of salicylic Acid after administration of trolamine salicylate cream in rats with transcutol((R)) and eucalyptus oil pre-treated skin. Adv Pharm Bull. 2013;3(2):295-301. doi: 10.5681/apb.2013.048. Epub 2013 Aug 20. [Article]
- 26. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 318-322). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- Health Canada: Triethanolamine Salicylate (Trolamine) Label [Link]
- External Links
- PubChem Compound
- 25213
- PubChem Substance
- 347827887
- ChemSpider
- 23549
- 38866
- ChEMBL
- CHEMBL2107288
- Wikipedia
- Trolamine_salicylate
- MSDS
- Download (47.5 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 data2 Terminated Treatment Cutaneous Mastocytoses 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 10 g/100mL Ointment Topical 13.3 % Cream Topical 10 g/100g Lotion Topical 10 % Spray Topical 100 mg/1mL Spray Topical 0.1 g/100mL Cream Topical 10 % w/w Cream Topical 15 % / g Cream Topical 0.1 g/1g Aerosol, foam Topical 0.1 g/1g Liquid Topical 10 g/100g Gel Topical 15 % Cream Topical 100 mg/1mL Lotion Topical 10 g/100g Aerosol, foam Topical 10 mg/100mL Lotion Topical Lotion Topical 10.0 % Cream Topical Cream Topical 15 % Cream Topical 15 % w/w Spray Topical 10 g/100mL Cream; kit; tablet, delayed release Oral; Topical Gel Topical 10 g/100mL Cream Topical 10 mg/1g Patch Topical 12.5 % Gel Topical Cream Cutaneous 10 g/1 Cream Topical 20 % Cream Topical 13.3 % Patch Topical Lotion Topical 10 g/100mL Cream Topical 13.3 % w/w Cream Topical 10 % Gel Topical 10 g/100g Gel Topical 10 % w/w Cream Topical 20 % w/w Salve Topical 100 mg/1g Gel Topical 100 mg/1mL Gel Topical 100 mg/1g Cream Topical 8.5 g/85g Cream Topical 100 mg/1g Liquid Topical 100 mg/1mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 50 MSDS boiling point (°C) Decomposes MSDS water solubility Soluble MSDS - Predicted Properties
Property Value Source Water Solubility 11.3 mg/mL ALOGPS logP 1.96 ALOGPS logP 1.98 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 2.79 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 35.3 m3·mol-1 Chemaxon Polarizability 12.82 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No 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 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]- 158.79921 predictedDeepCCS 1.0 (2019) [M+H]+ 161.15721 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.29376 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Topical Analgesic and Anesthetic Agents Drug Class Review [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Topical Analgesic and Anesthetic Agents Drug Class Review [Link]
Drug created at December 03, 2015 16:51 / Updated at October 05, 2024 03:14