Ecamsule

Identification

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Name
Ecamsule
Accession Number
DB09534
Type
Small Molecule
Groups
Approved
Description

Ecamsule is an organic compound which is added to many sunscreens to filter out UVA rays. It is a benzylidene camphor derivative, many of which are known for their excellent photostability. Ecamsule has been approved for use in the U.S. since 2006, but only at a specific concentration and only in a few products manufactured by L'Oreal. The company got approval for those products through a new drug application process.

Structure
Thumb
Synonyms
  • Ecamsule
  • Terephthalylidene dicamphor sulfonic acid
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
45 SPF High Protection Uva Uvb CreamEcamsule (2.0 %) + Avobenzone (3.5 %) + Drometrizole trisiloxane (3.0 %) + Octocrylene (10 %) + Titanium dioxide (3.3 %)CreamTopicalLaboratoires La Roche Posay Canada2008-04-162016-08-31Canada
Anthelios - Lait SPF 45Ecamsule (3.0 %) + Avobenzone (2.0 %) + Octocrylene (10.0 %) + Titanium dioxide (3.7 %)LotionTopicalLaboratoires La Roche Posay Canada2004-05-012008-06-20Canada
Anthelios Dermo-kidsEcamsule (1.5 %) + Avobenzone (3 %) + Drometrizole trisiloxane (4.5 %) + Octisalate (5 %) + Octocrylene (2.5 %) + Titanium dioxide (5.85 %)LotionTopicalLaboratoires La Roche Posay Canada2015-05-04Not applicableCanada
Anthelios L - Ecran Intolerances Solaires SPF 60Ecamsule (3.3 %) + Avobenzone (3.5 %) + Enzacamene (5 %) + Titanium dioxide (4 %)CreamTopicalLaboratoires La Roche Posay Canada1999-03-012009-06-05Canada
Anthelios L-lait Ecran Intol.solaire SPF 60Ecamsule (3.3 %) + Avobenzone (3.5 %) + Enzacamene (5 %) + Titanium dioxide (4 %)LotionTopicalCosmair Canada Inc.1996-12-312001-07-27Canada
Anthelios Lotion Corps Ultra-fluideEcamsule (2 %) + Avobenzone (3 %) + Homosalate (10 %) + Octisalate (5 %) + Octocrylene (5 %) + Oxybenzone (6 %)CreamTopicalLaboratoires La Roche Posay Canada2017-10-24Not applicableCanada
Anthelios MistEcamsule (2 %) + Avobenzone (3 %) + Homosalate (10 %) + Octisalate (5 %) + Octocrylene (5 %) + Oxybenzone (6 %)AerosolTopicalLaboratoires La Roche Posay Canada2015-05-04Not applicableCanada
Anthelios S - Ecran Solaire SPF 30Ecamsule (2 %) + Avobenzone (2 %) + Enzacamene (5 %) + Titanium dioxide (4 %)CreamTopicalLaboratoires La Roche Posay Canada1997-05-292010-06-08Canada
Anthelios SPF 45Ecamsule (1.0 %) + Avobenzone (3.0 %) + Bemotrizinol (0.5 %) + Drometrizole trisiloxane (0.5 %) + Octisalate (5.0 %) + Octocrylene (5.0 %) + Titanium dioxide (4.7 %)LotionTopicalLaboratoires La Roche Posay Canada2010-05-042015-08-07Canada
Anthelios Spray SPF 30Ecamsule (0.5 %) + Avobenzone (3.0 %) + Octisalate (5.0 %) + Octocrylene (10.0 %) + Titanium dioxide (5.6 %)LotionTopicalLaboratoires La Roche Posay Canada2005-06-012012-01-06Canada
International/Other Brands
Mexoryl SX
Categories
UNII
M94R1PM439
CAS number
92761-26-7
Weight
Average: 562.69
Monoisotopic: 562.169510403
Chemical Formula
C28H34O8S2
InChI Key
HEAHZSUCFKFERC-UHFFFAOYSA-N
InChI
InChI=1S/C28H34O8S2/c1-25(2)21-9-11-27(25,15-37(31,32)33)23(29)19(21)13-17-5-7-18(8-6-17)14-20-22-10-12-28(24(20)30,26(22,3)4)16-38(34,35)36/h5-8,13-14,21-22H,9-12,15-16H2,1-4H3,(H,31,32,33)(H,34,35,36)
IUPAC Name
{3-[(4-{[7,7-dimethyl-3-oxo-4-(sulfomethyl)bicyclo[2.2.1]heptan-2-ylidene]methyl}phenyl)methylidene]-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl}methanesulfonic acid
SMILES
CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)C2=CC1=CC=C(C=C2C3CCC(CS(O)(=O)=O)(C2=O)C3(C)C)C=C1

Pharmacology

Indication

Applied topically to filter out UVA rays.

Associated Conditions
Pharmacodynamics

When exposed to UV ecamsule undergoes reversible photoisomerization followed by photoexcitation. The absorbed UV is then released as thermal energy, without penetrating the skin, thereby protecting the skin from UV exposure.

Mechanism of action

Ecamsule protects against UV wavelengths in the 290–400 nanometer range, with peak protection at 345 nm. Ecamsule is photostable and it does not degrade significantly when exposed to light. In studies done in mice it reduces the formation of UV induced pyrimidine dimers and delays the onset of skin cancer. In vitro, ecamsule has been shown to effectively protect against the harmful effects of UV.

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

Ecamsule is a topical preparation, it should not be absorbed. Research done by L'Oreal on human subjects revealed that the systemically absorbed dose of [(14)C]-Ecamsule is less than 0.1% and under realistic exposure conditions, the human systemic exposure to this UVA filter is negligible and poses no risk to human health.

Volume of distribution

Ecamsule is intended for topical application and has no volume of distribution.

Protein binding

Ecamsule is intended for topical application only.

Metabolism

Ecamsule is not absorbed or metabolized.

Route of elimination

Ecamsule is intended for topical application only.

Half life

Ecamsule is not absorbed and has no reported half life data.

Clearance

Ecamsule is used topically, it not absorbed or metabolized.

Toxicity

The most common reactions were dermatitis, dry skin, acne, itching, redness and skin discomfort.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Marrot L, Belaidi JP, Chaubo C, Meunier JR, Perez P, Agapakis-Causse C: An in vitro strategy to evaluate the phototoxicity of solar UV at the molecular and cellular level: application to photoprotection assessment. Eur J Dermatol. 1998 Sep;8(6):403-12. [PubMed:9729050]
  2. Fourtanier A, Labat-Robert J, Kern P, Berrebi C, Gracia AM, Boyer B: In vivo evaluation of photoprotection against chronic ultraviolet-A irradiation by a new sunscreen Mexoryl SX. Photochem Photobiol. 1992 Apr;55(4):549-60. [PubMed:1320278]
  3. Seite S, Moyal D, Richard S, de Rigal J, Leveque JL, Hourseau C, Fourtanier A: Mexoryl SX: a broad absorption UVA filter protects human skin from the effects of repeated suberythemal doses of UVA. J Photochem Photobiol B. 1998 Jun 15;44(1):69-76. [PubMed:9745729]
  4. Benech-Kieffer F, Meuling WJ, Leclerc C, Roza L, Leclaire J, Nohynek G: Percutaneous absorption of Mexoryl SX in human volunteers: comparison with in vitro data. Skin Pharmacol Appl Skin Physiol. 2003 Nov-Dec;16(6):343-55. [PubMed:14528058]
  5. Wikipedia [Link]
External Links
PubChem Compound
9915879
PubChem Substance
347827874
ChemSpider
28534218
ChEBI
135830
ChEMBL
CHEMBL3989850
Wikipedia
Ecamsule

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingOtherSystemic Exposure to Sunscreen Ingredients1
4CompletedTreatmentMelasma1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
AerosolTopical
SprayTopical
StickTopical
GelTopical
CreamTopical
LotionTopical
EmulsionTopical
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00571 mg/mLALOGPS
logP0.37ALOGPS
logP4.1ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area142.88 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity143.56 m3·mol-1ChemAxon
Polarizability59.64 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Bicyclic monoterpenoids
Alternative Parents
Aromatic monoterpenoids / Benzene and substituted derivatives / Sulfonyls / Organosulfonic acids / Alkanesulfonic acids / Ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic monoterpenoid / Bornane monoterpenoid / Monocyclic benzene moiety / Benzenoid / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Organosulfonic acid / Sulfonyl / Alkanesulfonic acid / Ketone
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on November 30, 2015 12:10 / Updated on June 04, 2019 07:13