Identification
- Brand Names
- Max-freeze
- Generic Name
- Menthyl salicylate
- DrugBank Accession Number
- DB11201
- Background
Menthyl salicylate is an ester of menthol and salicylic acid 1.
This product is used to treat minor aches and pains of the muscles/joints (e.g., arthritis, backache, sprains) 2.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Menthyl salicylate (DB11201)
- Weight
- Average: 276.376
Monoisotopic: 276.172544633 - Chemical Formula
- C17H24O3
- Synonyms
- 1-Menthyl salicylate
- Menthyl salicylate, (+/-)-
Pharmacology
- Indication
For the temporary relief of pain associated with rheumatism, arthritis, neuralgia, sprains and strains of joints and muscles, lumbago and fibrositis 7.
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 for symptomatic treatment of Arthritis Combination Product in combination with: Levomenthol (DB00825) ••• ••• Used in combination for symptomatic treatment of Arthritis Combination Product in combination with: Levomenthol (DB00825), Camphor (DB01744) ••• ••• Used in combination for symptomatic treatment of Back pain Combination Product in combination with: Levomenthol (DB00825) ••• ••• Used in combination for symptomatic treatment of Back pain Combination Product in combination with: Camphor (DB01744), Levomenthol (DB00825) ••• ••• Used in combination for symptomatic treatment of Contusions Combination Product in combination with: Levomenthol (DB00825) ••• ••• - Contraindications & Blackbox Warnings
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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.2.
- 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 6.
Methyl salicylate is a salicylic acid derivative, and when combined with menthol, produces menthyl salicylate 6.
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 6.
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 6.
Target Actions Organism AProstaglandin G/H synthase 1 antagonistHumans AProstaglandin G/H synthase 2 antagonistHumans - 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 7.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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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 7.
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 7.
- 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 Menthyl salicylate is combined with Abciximab. Acebutolol Menthyl salicylate may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Menthyl salicylate. Acemetacin The risk or severity of adverse effects can be increased when Menthyl salicylate is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding and hemorrhage can be increased when Menthyl 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.- Active Moieties
Name Kind UNII CAS InChI Key Salicylic acid unknown O414PZ4LPZ 69-72-7 YGSDEFSMJLZEOE-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Calmomusc Liq Menthyl salicylate (6.3 %) + Eucalyptol (2.1 %) + Levomenthol (3.17 %) Liquid Topical Cardinaux Enrg Les Produits Naturels 1989-12-31 2000-07-07 Canada 
Dr. Ds Super 7 Pain Relief Menthyl salicylate (100 mg/1mL) + Menthol (20 mg/1mL) Cream Topical Promedx Innovations Inc 2019-09-04 Not applicable US 
Extra Strength Hua Tuo Medicated Plaster Menthyl salicylate (13.84 g/1) + Menthol (3.32 g/1) + Synthetic camphor (8.3 g/1) Plaster Topical; Transdermal Guangzhou Baiyunshan Jingxiutang Pharmaceutical Company 2013-06-17 Not applicable US Flexall Stick Menthyl salicylate (30 %) + Levomenthol (10 %) Stick Topical Chattem, Inc. 1997-08-07 2003-06-06 Canada Muscle Rub Ultra Menthyl salicylate (30 g/100g) + Camphor (4 g/100g) + Menthol (10 g/100g) Cream Topical H E B 2011-07-25 Not applicable US
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 / Monocyclic monoterpenoids / Menthane monoterpenoids / Aromatic monoterpenoids / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Carboxylic acid esters / Monocarboxylic acids and derivatives show 3 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic monoterpenoid show 9 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans
Chemical Identifiers
- UNII
- 43XOA705ZD
- CAS number
- 89-46-3
- InChI Key
- SJOXEWUZWQYCGL-DVOMOZLQSA-N
- InChI
- InChI=1S/C17H24O3/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16,18H,8-10H2,1-3H3/t12-,13+,16-/m1/s1
- IUPAC Name
- (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 2-hydroxybenzoate
- SMILES
- CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1O
References
- General References
- External Links
- ChemSpider
- 16736426
- 1368207
- ChEBI
- 135976
- ZINC
- ZINC000000002060
- MSDS
- Download (52.3 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Topical Plaster Topical; Transdermal Stick Topical Patch Topical Cream Topical Ointment Topical Gel Topical Patch Transdermal - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 186 MSDS logP 4.01 https://www.chemeo.com/cid/67-677-7/Menthyl%20salicylate - Predicted Properties
Property Value Source Water Solubility 0.0275 mg/mL ALOGPS logP 4.24 ALOGPS logP 5.51 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 9.72 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 79.25 m3·mol-1 Chemaxon Polarizability 31.14 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No 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 GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-7910000000-590d5d6835141226a159 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000b-9430000000-4b7ab32f35a2a7700e4a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0910000000-a637832f92eab7ef9670 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-2920000000-7e12b4aae0b20a54e360 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-3910000000-33ac2f71a7387e665393 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9220000000-c985e8b3bf74bc29d90b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4m-9710000000-e2a9c0f2529f357e0fda 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]- 163.6351 predictedDeepCCS 1.0 (2019) [M+H]+ 165.9931 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.8994 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
- Cronstein BN, Montesinos MC, Weissmann G: Salicylates and sulfasalazine, but not glucocorticoids, inhibit leukocyte accumulation by an adenosine-dependent mechanism that is independent of inhibition of prostaglandin synthesis and p105 of NFkappaB. Proc Natl Acad Sci U S A. 1999 May 25;96(11):6377-81. [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
- Cronstein BN, Montesinos MC, Weissmann G: Salicylates and sulfasalazine, but not glucocorticoids, inhibit leukocyte accumulation by an adenosine-dependent mechanism that is independent of inhibition of prostaglandin synthesis and p105 of NFkappaB. Proc Natl Acad Sci U S A. 1999 May 25;96(11):6377-81. [Article]
Drug created at December 03, 2015 16:51 / Updated at October 21, 2021 04:40