Meradimate

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

Similar Structures

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

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Associated Therapies

UV protection therapy

Contraindications & Blackbox Warnings

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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

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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

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dosage, form, labeller, route of administration, and marketing period.

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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
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
Aveda Botanical Kinetics Daily Light Guard	Meradimate (3.5 %) + Octinoxate (5 %) + Titanium dioxide (2 %)	Cream	Topical	Aveda Corporation	1994-12-31	1998-04-05
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
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
Blistex Lip Tone Balm	Meradimate (4 %) + Dimethicone (2 %) + Octinoxate (7.3 %)	Ointment; Stick	Topical	Blistex Corporation	1995-12-31	2003-07-01
Blistex Ultra Lip Balm	Meradimate (4.8 %) + Dimethicone (3 %) + Homosalate (4.5 %) + Octinoxate (7.4 %) + Octisalate (5 %) + Oxybenzone (5.2 %)	Ointment	Topical	Blistex Corporation	1994-12-31	Not applicable
Body Armor - SPF 30 Sunscreen	Meradimate (3.9 %) + Octinoxate (5.63 %) + Octisalate (3.75 %) + Octocrylene (3 %)	Cream	Topical	P T Technologies, Inc.	1995-12-31	2001-09-17
Body Armor Sun 'n Bug Block	Meradimate (3.5 %) + Octinoxate (4.75 %) + Octisalate (2.75 %)	Cream	Topical	P T Technologies, Inc.	1999-02-27	2001-09-17
Bull Frog Water Armor Super 40	Meradimate (5 g/100g) + Octinoxate (7.5 g/100g) + Octisalate (5 g/100g) + Octocrylene (10 g/100g) + Oxybenzone (6 g/100g) + Titanium dioxide (4.5 g/100g)	Lotion	Topical	Sun & Skin Care Research, Inc	2013-06-01	Not applicable

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

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

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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
RxNav: 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	Completed	Treatment	Foot Dryness in Patients With NIDDM / Foot Transepidermal Water Loss in Patients in NIDDM	1
Not Available	Terminated	Treatment	Diaper Rash	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, 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

Drug created at December 03, 2015 16:51 / Updated at September 28, 2021 21:54