Identification
- Summary
Meradimate is an ingredient used in sunscreens to absorb UV radiation.
- Generic Name
- Meradimate
- DrugBank Accession Number
- DB11096
- Background
Meradimate, before known as menthyl anthranilate, is used in a maximal concentration of 5% in different products as a UV filter.3 It is currently required to be named as meradimate in all FDA approved OTC products. Meradimate is approved by the FDA and Health Canada to be used as an ingredient in sunblocking products.6,5
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Meradimate (DB11096)
- Weight
- Average: 275.392
Monoisotopic: 275.188529049 - Chemical Formula
- C17H25NO2
- Synonyms
- Menthyl anthranilate
- Menthyl-O-aminobenzoate
- Meradimate
Pharmacology
- Indication
Meradimate is used as an active ingredient in sunscreens or as a sunblock factor in different products. It fits under the category of broad-spectrum absorbent agent. These characteristics are important to consider due to the fact that this kind of ingredients can either absorb or reflect UV radiation. It is also important to know the type of rays that cover. UVA rays are the responsible of causing sun damage and reaching deeper layers of the skin while UVB can only cause sunburn in the outer layer of the skin. When an agent is of broad spectrum, this means that this agent is capable of acting in both UVA and UVB rays.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 Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Meradimate effect provides a low-level, broad-spectrum protecting coverage effect.3
- Mechanism of action
Meradimate acts by absorbing both the UVA and UVB radiation, this provides this ingredient with a broad spectrum and it explains why it is highly used in different products such as lip balms, lipsticks, and moisturizers.7 Its protective effective action does not cover completely the UVA rays as it only reaches 336 nm.2 This has been proven even thought meradimate has a theoretical protective coverage range between 200-380 nm.3 Its function is related to the intrinsic structure of meradimate which is an ortho-disubstituted aminobenzoate. This structure allows easy electron delocalization and shifts in the maximum absorption.4
- Absorption
Meradimate is not absorbed through the skin.7
- Volume of distribution
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
- Protein binding
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
- Metabolism
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
- Route of elimination
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
- Half-life
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
- Clearance
As meradimate is not absorbed, this pharmacokinetic property is not relevant.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Meradimate is considered safe but some studies have shown that it can increase the production of reactive oxygen species.4
- 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.Not Available
- 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.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image All Seasons Lip Balm Meradimate (4.8 % w/w) + Homosalate (4.5 % w/w) + Octinoxate (7.4 % w/w) + Octisalate (5.0 % w/w) + Oxybenzone (5.2 % w/w) Stick Topical Empack Spraytech Inc 2009-09-04 2021-08-10 Canada 
Aloe Up Medicated Lip Ice Sunscreen SPF 30 Meradimate (4 g/100g) + Homosalate (6 g/100g) + Octinoxate (7.5 g/100g) + Oxybenzone (5 g/100g) Lipstick Topical Aloe Care International, Llc 2014-02-24 Not applicable US 
Aveda Botanical Kinetics Daily Light Guard Meradimate (3.5 %) + Octinoxate (5 %) + Titanium dioxide (2 %) Cream Topical Aveda Corporation 1994-12-31 1998-04-05 Canada Biocorneum Plus Broad Spectrum SPF 30 Advanced Scar Treatment Meradimate (5 g/100g) + Avobenzone (3 g/100g) + Homosalate (15 g/100g) + Octisalate (5 g/100g) + Octocrylene (10 g/100g) Gel Topical Sientra, Inc 2020-03-31 Not applicable US BIOCORNEUM PLUS BROAD SPECTRUM SPF 30 ADVANCED SCAR TREATMENT gel Meradimate (5 g/100g) + Avobenzone (3 g/100g) + Homosalate (15 g/100g) + Octisalate (5 g/100g) + Octocrylene (10 g/100g) Gel Topical Sientra, Inc. 2021-11-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Sodium Sulfacetamide Sulfur Meradimate (50 mg/1g) + Octasulfur (40 mg/1mL) + Sulfacetamide sodium (100 mg/1mL) + Titanium dioxide (50 mg/1g) Kit Topical River's Edge Pharmaceuticals, LLC 2008-06-01 2011-08-31 US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Aromatic monoterpenoids
- Alternative Parents
- Monocyclic monoterpenoids / Menthane monoterpenoids / Benzoic acid esters / Aminobenzoic acids and derivatives / Benzoyl derivatives / Aniline and substituted anilines / Vinylogous amides / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives show 5 more
- Substituents
- Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J9QGD60OUZ
- CAS number
- 134-09-8
- InChI Key
- SOXAGEOHPCXXIO-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3
- IUPAC Name
- 5-methyl-2-(propan-2-yl)cyclohexyl 2-aminobenzoate
- SMILES
- CC(C)C1CCC(C)CC1OC(=O)C1=CC=CC=C1N
References
- General References
- Latha MS, Martis J, Shobha V, Sham Shinde R, Bangera S, Krishnankutty B, Bellary S, Varughese S, Rao P, Naveen Kumar BR: Sunscreening agents: a review. J Clin Aesthet Dermatol. 2013 Jan;6(1):16-26. [Article]
- Encyclopedia (2007). The encyclopedia of Ultraviolet Filters. Allured.
- Draelos D. and Thaman L. (2006). Cosmetic formulation of skin care products. Taylor and Francis Group. [ISBN:978-0-8493-3968-4]
- IARC Working Group (2001). IARC Handbooks of Cancer Prevention. WHO.
- FDA [Link]
- Health Canada [Link]
- Dermapproved [Link]
- External Links
- ChemSpider
- 8312
- 91324
- ChEBI
- 135974
- ChEMBL
- CHEMBL1597075
- Wikipedia
- Menthyl_anthranilate
- MSDS
- Download (107 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Diabetes Complications 1 3 Recruiting Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 2 Active Not Recruiting Supportive Care CNS Tumor, Childhood / Dermatitis / Pediatric Cancer 1 Not Available Active Not Recruiting Treatment Photodamaged Skin / Volume Deficiency of the Midface 1 Not Available Completed Treatment Foot Dryness in Patients With NIDDM / Foot Transepidermal Water Loss in Patients in NIDDM 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lipstick Topical Gel Topical Ointment; stick Topical Lotion Topical Spray Topical Cream Topical Stick Topical Ointment Topical Lotion Cutaneous Kit Topical Liquid Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 63 ºC 'MSDS' boiling point (°C) 177-179 ºC 'MSDS' water solubility Insoluble 'MSDS' - Predicted Properties
Property Value Source Water Solubility 0.00587 mg/mL ALOGPS logP 4.12 ALOGPS logP 4.98 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 19.39 Chemaxon pKa (Strongest Basic) 2.28 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 52.32 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 81.97 m3·mol-1 Chemaxon Polarizability 31.56 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes 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 MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0910000000-e7d7880546a317d84e9e Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-009t-9680000000-030bb07e7cd13d4e72ca Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0079-1920000000-194f19de0fee154238b4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-3910000000-8b254940fca11d038728 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9110000000-04fba14bc4e3b2d1b894 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052f-9710000000-325e11cc844bac947a99 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]- 166.52995 predictedDeepCCS 1.0 (2019) [M+H]+ 168.88795 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.9811 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at September 28, 2021 21:54