Trolamine salicylate
Identification
- Name
- Trolamine salicylate
- Accession Number
- DB11079
- Description
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
- Not Available
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.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
It is hazardous in case of ingestion MSDS. The carcinogenicity, mutagenicity and effects on reproductive fertility of trolamine salicylate have not been reported.
- Affected organisms
- Not Available
- 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 Unlock Additional DataAbciximab 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 Acemetacin is combined with Trolamine salicylate. Acenocoumarol The risk or severity of bleeding can be increased when Trolamine salicylate is combined with Acenocoumarol. Acetohexamide Trolamine salicylate may increase the hypoglycemic activities of Acetohexamide. Acetylsalicylic acid The therapeutic efficacy of Trolamine salicylate can be decreased when used in combination with Acetylsalicylic acid. Albiglutide Trolamine salicylate may increase the hypoglycemic activities of Albiglutide. Alclofenac The risk or severity of adverse effects can be increased when Alclofenac is combined with Trolamine salicylate. Alogliptin Trolamine salicylate may increase the hypoglycemic activities of Alogliptin. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- No interactions found.
Products
- 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 Unlock Additional DataAbr 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 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 Topical Alcis Health Inc. Not applicable Not applicable Canada Analgesic Cream 10 g/100g Topical Meijer Distribution 1990-04-15 2012-11-12 US Analgesic Cream Cream Topical Pharmascience Inc 2013-10-08 Not applicable Canada Analgesic Cream Extra Strength Odorless Cream Topical Pharmascience Inc 1999-10-09 2020-02-17 Canada Analgesic Creme Rub Cream 100 mg/1g Topical Major Pharmaceuticals 2014-05-10 2018-08-06 US Antiphlogistine Rub A-535 No Odour Fmla Ont Ointment Topical Carter Products, Division Of Carter Wallace Ns Inc. 1993-12-31 1997-08-14 Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Arthritis Extra Strength Roll-ON Lotion Trolamine salicylate (10 %) + Capsaicin (0.035 %) + Levomenthol (1.25 %) Lotion Topical Church & Dwight Canada Corp 2008-09-15 2019-10-23 Canada Arthritis Pain Relief Trolamine salicylate (10 %) + Capsaicin (0.035 %) + Levomenthol (1.25 %) 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 Inflatherm Trolamine salicylate (8.5 g/85g) + Diclofenac sodium (75 mg/1) Oral; Topical V2 Pharma 2019-06-03 2019-06-03 US Inmotion Pain Creme Original Strength Trolamine salicylate (20 mg/1mL) + Levomenthol (30 mg/1mL) Cream Topical Inmotion Products LLC 2019-05-12 Not applicable US Inmotion Pain Creme Ultra Strength Trolamine salicylate (20 mg/1mL) + Levomenthol (40 mg/1mL) Cream Topical Inmotion Products LLC 2019-05-12 Not applicable US Myoflex Extra Strength Ice Trolamine salicylate (15 %) + Levomenthol (3 %) Gel Topical Bayer Inc Consumer Care 2003-10-30 2007-08-02 Canada Myoflex Ice Cold Plus - Gel Trolamine salicylate (15 %) + Levomenthol (3 %) Gel Topical Sterling Winthrop Inc. 1994-12-31 1996-09-10 Canada - 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
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. [PubMed:19078236]
- 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. [PubMed:18796932]
- 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. [PubMed:8876850]
- 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. [PubMed:24312851]
- 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
- AHFS Codes
- 28:08.04.24 — Salicylates
- MSDS
- Download (47.5 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 10 g/100mL Ointment Topical Cream Topical 10 g/100g Cream Topical 10 % Spray Topical 100 mg/1mL Spray Topical 0.1 g/100mL Liquid Topical 10 g/100g Gel Topical Cream Topical 100 mg/1mL Lotion Topical 10 g/100g Aerosol, foam Topical 10 mg/100mL Lotion Topical Lotion Topical Cream Topical Spray Topical 10 g/100mL Cream Topical Cream Topical 10 mg/1g Patch Topical Gel Topical Cream Cutaneous 10 g/1 Patch Topical Lotion Topical 10 g/100mL Gel Topical 10 g/100g 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 MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Topical Analgesic and Anesthetic Agents Drug Class Review [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Topical Analgesic and Anesthetic Agents Drug Class Review [Link]
Drug created on December 03, 2015 09:51 / Updated on January 23, 2021 21:03