Meradimate

Identification

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Name
Meradimate
Accession Number
DB11096
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • Menthyl anthranilate
  • Menthyl-O-aminobenzoate
  • Meradimate
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
All Seasons Lip BalmMeradimate (4.8 %) + Homosalate (4.5 %) + Octinoxate (7.4 %) + Octisalate (5.0 %) + Oxybenzone (5.2 %)StickTopicalEmpack Spraytech Inc.2009-09-04Not applicableCanada
Aloe Up Medicated Lip Ice Sunscreen SPF 30Meradimate (4 g/100g) + Homosalate (6 g/100g) + Octinoxate (7.5 g/100g) + Oxybenzone (5 g/100g)LipstickTopicalAloe Care International, Llc2014-02-24Not applicableUs
Aveda Botanical Kinetics Daily Light GuardMeradimate (3.5 %) + Octinoxate (5 %) + Titanium dioxide (2 %)CreamTopicalAveda Corporation1994-12-311998-04-05Canada
Blistex Lip Tone BalmMeradimate (4 %) + Dimethicone (2 %) + Octinoxate (7.3 %)Ointment; StickTopicalBlistex Corporation1995-12-312003-07-01Canada
Blistex Ultra Lip BalmMeradimate (4.8 %) + Dimethicone (3 %) + Homosalate (4.5 %) + Octinoxate (7.4 %) + Octisalate (5 %) + Oxybenzone (5.2 %)OintmentTopicalBlistex Corporation1994-12-31Not applicableCanada
Body Armor - SPF 30 SunscreenMeradimate (3.9 %) + Octinoxate (5.63 %) + Octisalate (3.75 %) + Octocrylene (3 %)CreamTopicalP T Technologies, Inc.1995-12-312001-09-17Canada
Body Armor Sun 'n Bug BlockMeradimate (3.5 %) + Octinoxate (4.75 %) + Octisalate (2.75 %)CreamTopicalP T Technologies, Inc.1999-02-272001-09-17Canada
Bull Frog Water Armor Super 40Meradimate (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)LotionTopicalSun & Skin Care Research, Inc2013-06-01Not applicableUs
BullFrog Super BlockMeradimate (0.05 g/1mL) + Octinoxate (0.075 g/1mL) + Octisalate (0.05 g/1mL) + Octocrylene (0.1 g/1mL) + Oxybenzone (0.06 g/1mL) + Titanium dioxide (0.07 g/1mL)SprayTopicalChattem, Inc.2009-11-012016-05-18Us
BullFrog Water Armor Sport SuperMeradimate (0.05 g/1mL) + Octinoxate (0.075 g/1mL) + Octisalate (0.05 g/1mL) + Octocrylene (0.1 g/1mL) + Oxybenzone (0.06 g/1mL) + Titanium dioxide (0.045 g/1mL)LotionTopicalChattem, Inc.2011-11-012015-05-08Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Sodium Sulfacetamide SulfurMeradimate (50 mg/1g) + Octasulfur (40 mg/1mL) + Sulfacetamide sodium (100 mg/1mL) + Titanium dioxide (50 mg/1g)KitTopicalRiver's Edge Pharmaceuticals, LLC2008-06-012011-08-31Us
Categories
UNII
J9QGD60OUZ
CAS number
134-09-8
Weight
Average: 275.392
Monoisotopic: 275.188529049
Chemical Formula
C17H25NO2
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

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

Associated Therapies
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

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

Toxicity

Meradimate is considered safe but some studies have shown that it can increase the production of reactive oxygen species.4

Affected organisms
Not Available
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
Not Available

References

General References
  1. 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. [PubMed:23320122]
  2. Encyclopedia (2007). The encyclopedia of Ultraviolet Filters. Allured.
  3. Draelos D. and Thaman L. (2006). Cosmetic formulation of skin care products. Taylor and Francis Group. [ISBN:978-0-8493-3968-4]
  4. IARC Working Group (2001). IARC Handbooks of Cancer Prevention. WHO.
  5. FDA [Link]
  6. Health Canada [Link]
  7. Dermapproved [Link]
External Links
ChemSpider
8312
ChEBI
135974
ChEMBL
CHEMBL1597075
Wikipedia
Menthyl_anthranilate
MSDS
Download (107 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentFoot Dryness in Patients With NIDDM / Foot Transepidermal Water Loss in Patients in NIDDM1
Not AvailableTerminatedTreatmentDiaper Rash1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Ointment; stickTopical
LotionTopical
SprayTopical
CreamTopical
LipstickTopical
StickTopical
OintmentTopical
LotionCutaneous
KitTopical
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)63 ºC'MSDS'
boiling point (°C)177-179 ºC'MSDS'
water solubilityInsoluble'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility0.00587 mg/mLALOGPS
logP4.12ALOGPS
logP4.98ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.39ChemAxon
pKa (Strongest Basic)2.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity81.97 m3·mol-1ChemAxon
Polarizability31.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Aminobenzoic acid or derivatives / Aromatic monoterpenoid / Benzoate ester / Monocyclic monoterpenoid / P-menthane monoterpenoid / Benzoic acid or derivatives / Aniline or substituted anilines / Benzoyl / Benzenoid / Monocyclic benzene moiety
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on December 03, 2015 09:51 / Updated on September 02, 2019 19:20