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Trolamine salicylate | CAS No: 2174-16-5 | GMP-certified suppliers
A medication that provides temporary topical relief of muscle and joint aches, including arthritis, backache, strains, sprains, bruises, and tendon or ligament pain.
Therapeutic categories
Acids, CarbocyclicAgents causing hyperkalemiaAnti-Inflammatory AgentsAnti-Inflammatory Agents, Non-SteroidalAnti-Inflammatory Agents, Non-Steroidal (Non-Selective)Benzene Derivatives
Generic name
Trolamine salicylate
Molecule type
small molecule
CAS number
2174-16-5
DrugBank ID
DB11079
Approval status
Approved drug
Primary indications
- 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
Product Snapshot
- Trolamine salicylate is available in multiple topical formulations including cream, ointment, lotion, spray, gel, foam, aerosol, patch, salve, and oral tablet forms
- It is primarily indicated for the temporary relief of musculoskeletal pain associated with conditions such as backache, strains, sprains, and arthritic or rheumatic pain
- The compound is approved for use in key regulatory markets including the US and Canada
Clinical Overview
Trolamine salicylate is a topical analgesic compound formed by the salt of triethanolamine and salicylic acid, classified chemically as a 1,2-aminoalcohol. It is indicated for the temporary relief of minor aches and pains associated with musculoskeletal conditions including arthritis, simple backache, lumbago, muscle strains, sprains, bruises, as well as tendon and ligament pain. Its neutralization of salicylic acid’s acidity by triethanolamine facilitates a formulation with diminished skin irritation potential and an absence of odor, enhancing patient acceptability.
Pharmacodynamically, trolamine salicylate acts as a non-selective inhibitor of cyclo-oxygenase (COX) enzymes, particularly COX-2, which is upregulated during inflammatory responses. By inhibiting COX activity, the compound reduces the synthesis of prostaglandins and thromboxanes, key mediators of inflammation and nociceptive sensitization responsible for pain. This mechanism underpins its analgesic effect in alleviating mild to moderate pain from inflammatory conditions affecting muscles and joints.
Absorption of trolamine salicylate after topical application is low, which limits systemic exposure and reduces the likelihood of systemic adverse effects commonly associated with oral salicylates. The compound exhibits low skin irritancy, contributing to its suitability for repeated topical use. In clinical contexts, topical formulations containing trolamine salicylate have demonstrated efficacy in temporary pain relief for conditions such as osteoarthritis of the hands and exercise-induced muscle soreness.
Safety considerations align with those typical of non-selective non-steroidal anti-inflammatory drugs (NSAIDs), including caution in patients with salicylate hypersensitivity and avoidance of use on broken or irritated skin. There is potential for nephrotoxicity with extensive or prolonged use due to systemic absorption, albeit minimal with topical administration.
Trolamine salicylate is incorporated in various over-the-counter topical analgesic products globally. For API procurement, ensuring compliance with pharmacopeial purity standards and confirming the absence of residual solvents or impurities is critical. Stability under formulation conditions and batch-to-batch consistency are important quality considerations to support safe and effective topical drug product manufacturing.
Pharmacodynamically, trolamine salicylate acts as a non-selective inhibitor of cyclo-oxygenase (COX) enzymes, particularly COX-2, which is upregulated during inflammatory responses. By inhibiting COX activity, the compound reduces the synthesis of prostaglandins and thromboxanes, key mediators of inflammation and nociceptive sensitization responsible for pain. This mechanism underpins its analgesic effect in alleviating mild to moderate pain from inflammatory conditions affecting muscles and joints.
Absorption of trolamine salicylate after topical application is low, which limits systemic exposure and reduces the likelihood of systemic adverse effects commonly associated with oral salicylates. The compound exhibits low skin irritancy, contributing to its suitability for repeated topical use. In clinical contexts, topical formulations containing trolamine salicylate have demonstrated efficacy in temporary pain relief for conditions such as osteoarthritis of the hands and exercise-induced muscle soreness.
Safety considerations align with those typical of non-selective non-steroidal anti-inflammatory drugs (NSAIDs), including caution in patients with salicylate hypersensitivity and avoidance of use on broken or irritated skin. There is potential for nephrotoxicity with extensive or prolonged use due to systemic absorption, albeit minimal with topical administration.
Trolamine salicylate is incorporated in various over-the-counter topical analgesic products globally. For API procurement, ensuring compliance with pharmacopeial purity standards and confirming the absence of residual solvents or impurities is critical. Stability under formulation conditions and batch-to-batch consistency are important quality considerations to support safe and effective topical drug product manufacturing.
Identification & chemistry
| Generic name | Trolamine salicylate |
|---|---|
| Molecule type | Small molecule |
| CAS | 2174-16-5 |
| UNII | H8O4040BHD |
| DrugBank ID | DB11079 |
Pharmacology
| Summary | Trolamine salicylate acts as a non-steroidal anti-inflammatory agent by inhibiting cyclo-oxygenase enzymes COX-1 and COX-2, reducing the synthesis of prostaglandins and thromboxanes involved in inflammatory responses. It targets COX-2 induction in inflammatory cells, thereby mediating analgesic effects in conditions characterized by mild to moderate musculoskeletal pain and inflammation. Its pharmacodynamic action results in temporary relief of muscle and joint pain associated with various musculoskeletal disorders. |
|---|---|
| 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 . 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 . Trolamine salicylate mediates its analgesic effect by inhibiting the production of inflammatory mediators that sensitize nociceptive nerve endings and generate pain . |
| 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 . 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 . In subjects with osteoarthritis in hands, trolamine salicylate cream was shown to be effective in achieving temporary relief of minor pain and stiffness . |
Targets
| Target | Organism | Actions |
|---|---|---|
| Prostaglandin G/H synthase 1 | Humans | inhibitor |
| Prostaglandin G/H synthase 2 | Humans | inhibitor |
ADME / PK
| Absorption | Following topical administration of 10% trolamine salicylate in healthy volunteers, salicylic acid could not be detected in serum indicating low systemic absorption . |
|---|---|
| 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 . |
| 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 . |
Formulation & handling
- Trolamine salicylate is primarily formulated for topical application in various forms such as creams, gels, lotions, and sprays.
- It is a small molecule with moderate water solubility and logP, suitable for cutaneous rather than injectable formulations.
- Oral delayed-release formulations are available, indicating potential sensitivity to gastric conditions requiring targeted release.
Regulatory status
| Lifecycle | The active pharmaceutical ingredient (API) is approaching patent expiry in key markets, including the US and Canada, where multiple generic formulations are emerging. This transition indicates a maturation phase with increasing competition and broader market accessibility. |
|---|
| Markets | US, Canada |
|---|
Supply Chain
| Supply chain summary | Trolamine salicylate is marketed primarily in the US and Canadian markets with multiple branded products available. The originator companies have established a presence through these branded formulations, indicating a competitive landscape. Patent expirations suggest that generic versions may already be on the market or forthcoming, contributing to broader sourcing options. |
|---|
Safety
| Toxicity | It is hazardous in case of ingestion [MSDS]. The carcinogenicity, mutagenicity and effects on reproductive fertility of trolamine salicylate have not been reported. |
|---|
High Level Warnings:
- Hazardous if ingested
- Avoid oral exposure
- Carcinogenicity, mutagenicity, and reproductive toxicity have not been established
Trolamine salicylate is a type of Anti-inflammatory Agents
Anti-inflammatory agents are a crucial category of pharmaceutical active pharmaceutical ingredients (APIs) used to treat various inflammatory conditions. These agents play a vital role in alleviating pain, reducing swelling, and controlling inflammation in the body. They are widely employed in the management of diverse medical conditions, including arthritis, autoimmune disorders, asthma, and skin conditions like dermatitis.
Anti-inflammatory APIs primarily function by inhibiting the production of specific enzymes called cyclooxygenases (COX) and lipoxygenases (LOX). These enzymes are responsible for the synthesis of pro-inflammatory molecules known as prostaglandins and leukotrienes, respectively. By suppressing the activity of COX and LOX, anti-inflammatory agents effectively curtail the production of these inflammatory mediators, thereby mitigating inflammation.
Common examples of anti-inflammatory APIs include non-steroidal anti-inflammatory drugs (NSAIDs) like ibuprofen, aspirin, and naproxen. These agents exhibit analgesic, antipyretic, and anti-inflammatory properties. Another group of anti-inflammatory APIs includes corticosteroids, such as prednisone and dexamethasone, which are synthetic hormones that modulate the body's immune response to control inflammation.
In conclusion, anti-inflammatory agents are a vital category of pharmaceutical APIs widely used to manage inflammation-related disorders. They target enzymes involved in the synthesis of pro-inflammatory molecules, effectively reducing pain and swelling. NSAIDs and corticosteroids are commonly prescribed anti-inflammatory APIs due to their efficacy in controlling inflammation.
