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- Menthyl salicylate
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Menthyl salicylate | CAS No: 89-46-3 | GMP-certified suppliers
A medication that provides temporary relief from pain and inflammation associated with rheumatism, arthritis, neuralgia, sprains, strains, lumbago, and fibrositis.
Therapeutic categories
Anti-Inflammatory AgentsAnti-Inflammatory Agents, Non-Steroidal
Generic name
Menthyl salicylate
Molecule type
small molecule
CAS number
89-46-3
DrugBank ID
DB11201
Approval status
Approved drug
Primary indications
- For the temporary relief of pain associated with rheumatism, arthritis, neuralgia, sprains and strains of joints and muscles, lumbago and fibrositis
Product Snapshot
- Menthyl salicylate is available in topical formulations including liquid, plaster, stick, patch, cream, ointment, and gel forms
- It is primarily indicated for the temporary relief of pain related to rheumatism, arthritis, neuralgia, sprains, strains, lumbago, and fibrositis
- This API is approved for use in the Canadian and US markets
Clinical Overview
Menthyl salicylate (CAS: 89-46-3) is an ester formed from menthol and salicylic acid, classified among o-hydroxybenzoic acid esters. It is utilized primarily for the temporary relief of minor musculoskeletal discomfort, including conditions such as rheumatism, arthritis, neuralgia, sprains, strains, lumbago, and fibrositis.
The compound exerts its therapeutic effects through the combined pharmacological actions of its constituent parts. Menthol acts as a vasodilator on cutaneous blood vessels, eliciting a cooling sensation followed by warmth that serves as a counterirritant. This sensory irritation can modulate nociceptor activity, potentially interfering with pain signal transmission. Additionally, menthol functions as a skin penetration enhancer, facilitating more rapid absorption of active agents. Methyl salicylate, derived from salicylic acid, contributes topical analgesic and anesthetic effects through the inhibition of cyclooxygenase enzymes, resulting in decreased prostaglandin synthesis. This reduction can diminish inflammation and pain at the site of application.
Pharmacokinetic data indicate that methyl salicylate is absorbed through the skin upon topical administration, enabling localized therapeutic action. The metabolism of methyl salicylate shares similarities with other salicylate derivatives; however, systemic exposure is typically limited when used as directed.
Safety considerations for menthyl salicylate include potential skin irritation or allergic reactions. Care should be taken to avoid application on broken skin or mucous membranes. Given the salicylate component, caution is advised in populations sensitive to salicylates or those concurrently using anticoagulants due to possible platelet function effects. Standard regulatory approvals classify this compound as an approved non-steroidal anti-inflammatory agent for topical use.
In pharmaceutical development and sourcing, consistent quality of menthyl salicylate API is critical. Suppliers should demonstrate compliance with relevant pharmacopeial standards and provide comprehensive certificates of analysis, ensuring purity, concentration, and absence of contaminants to facilitate reliable incorporation into topical formulations.
The compound exerts its therapeutic effects through the combined pharmacological actions of its constituent parts. Menthol acts as a vasodilator on cutaneous blood vessels, eliciting a cooling sensation followed by warmth that serves as a counterirritant. This sensory irritation can modulate nociceptor activity, potentially interfering with pain signal transmission. Additionally, menthol functions as a skin penetration enhancer, facilitating more rapid absorption of active agents. Methyl salicylate, derived from salicylic acid, contributes topical analgesic and anesthetic effects through the inhibition of cyclooxygenase enzymes, resulting in decreased prostaglandin synthesis. This reduction can diminish inflammation and pain at the site of application.
Pharmacokinetic data indicate that methyl salicylate is absorbed through the skin upon topical administration, enabling localized therapeutic action. The metabolism of methyl salicylate shares similarities with other salicylate derivatives; however, systemic exposure is typically limited when used as directed.
Safety considerations for menthyl salicylate include potential skin irritation or allergic reactions. Care should be taken to avoid application on broken skin or mucous membranes. Given the salicylate component, caution is advised in populations sensitive to salicylates or those concurrently using anticoagulants due to possible platelet function effects. Standard regulatory approvals classify this compound as an approved non-steroidal anti-inflammatory agent for topical use.
In pharmaceutical development and sourcing, consistent quality of menthyl salicylate API is critical. Suppliers should demonstrate compliance with relevant pharmacopeial standards and provide comprehensive certificates of analysis, ensuring purity, concentration, and absence of contaminants to facilitate reliable incorporation into topical formulations.
Identification & chemistry
| Generic name | Menthyl salicylate |
|---|---|
| Molecule type | Small molecule |
| CAS | 89-46-3 |
| UNII | 43XOA705ZD |
| DrugBank ID | DB11201 |
Pharmacology
| Summary | Menthol acts as a vasodilator and nerve signal modulator, producing a cooling sensation followed by analgesia, and enhances drug penetration through the skin. Methyl salicylate, a salicylate derivative, inhibits cyclooxygenase enzymes (COX-1 and COX-2), reducing prostaglandin synthesis and exerting topical analgesic and counterirritant effects. Together, these agents provide symptomatic relief of musculoskeletal pain by modulating local inflammatory mediators and sensory nerve transmission. |
|---|---|
| Mechanism of action | Menthol dilates the blood vessels causing a sensation of coldness, followed by an analgesic effect. Menthol also acts as a penetration enhancer, increasing the penetration of drugs when applied on the skin, to give a faster onset of action . Methyl salicylate is a salicylic acid derivative, and when combined with menthol, produces menthyl salicylate . Salicylates inhibit cyclooxygenase, thereby reducing the formation of prostaglandins, and cause platelet dysfunction Methyl salicylate is used topically as a counter-irritant. Upon application, it is absorbed through the skin and is applied for the relief of pain in rheumatic conditions and painful muscle or joints . The menthol dilates blood vessels, why the salicylate portion provides a topical anesthetic and analgesic action on the affected area. The cooling and warning action may interfere with the transmission of pain signals through nerves . |
| Pharmacodynamics | Menthol and methyl salicylate are known as counterirritants. They work by causing the skin to feel cool and then warm. Used together, they provide symptomatic relief for mild to moderate muscular and joint aches and pains, muscle cramps, shoulder aches and stiff neck.. |
Targets
| Target | Organism | Actions |
|---|---|---|
| Prostaglandin G/H synthase 1 | Humans | antagonist |
| Prostaglandin G/H synthase 2 | Humans | antagonist |
ADME / PK
| Absorption | May be absorbed through intact skin. The absorption of topical salicylates is proportional to the surface area exposed, the duration of exposure, concentration and skin integrity. Absorption characteristics of salicylates vary with the dose, formulation, and route of administration. Percutaneous absorption is enhanced by exercise, heat, occlusion, or disruption of the integrity of the skin or application to large areas of skin. Both the rate and extent of absorption increases after continuous application, increasing its bioavailability . |
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Formulation & handling
- Menthyl salicylate is a small molecule with primarily topical and transdermal administration routes, not intended for oral or injectable use.
- Low water solubility and high lipophilicity (LogP 5.51) suggest formulation in lipophilic vehicles or gels for effective skin penetration.
- Handling should consider its liquid state and sensitivity to oxidation; appropriate packaging to limit exposure to air and light is recommended.
Regulatory status
| Lifecycle | The active pharmaceutical ingredient (API) is marketed in both Canada and the US, with key patents having expired, leading to increased availability of generic formulations and a mature market landscape. |
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| Markets | Canada, US |
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Supply Chain
| Supply chain summary | Menthyl salicylate is supplied by multiple originator companies with branded products available primarily in the US and Canadian markets. The presence of various brand formulations indicates a competitive manufacturing landscape with established global distribution in North America. Patent expiry timelines suggest that generic competition may already exist or is likely to emerge, contributing to a diversified supply chain. |
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Safety
| Toxicity | Salicylate intoxication may occur after ingestion or topical application of menthyl salicylate. Mild chronic salicylate intoxication, also known as _salicylism_, normally occurs only after repeated use of large doses. Salicylism can also occur following the excessive topical application of salicylates. Symptoms of toxicity include dizziness, tinnitus, deafness, sweating, nausea and vomiting, headache, and confusion, and may be controlled by reducing the dosage . Symptoms of more severe intoxication or of acute poisoning following overdose include hyperventilation, fever, restlessness, ketosis, and respiratory alkalosis and metabolic acidosis. Depression of the CNS may lead to coma, cardiovascular collapse and respiratory failure may also result . |
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High Level Warnings:
- Menthyl salicylate may cause systemic salicylate toxicity upon excessive topical or oral exposure
- Prolonged or high-dose use can lead to salicylism, characterized by neurological and auditory symptoms
- Severe overdose risk includes central nervous system depression, metabolic disturbances, and potential respiratory or cardiovascular failure
Menthyl 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.
