Ecamsule

Identification

Name
Ecamsule
Accession Number
DB09534
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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 562.69
Monoisotopic: 562.169510403
Chemical Formula
C28H34O8S2
Synonyms
  • Ecamsule
  • Terephthalylidene dicamphor sulfonic acid

Pharmacology

Indication

Applied topically to filter out UVA rays.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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.

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.

Adverse Effects
Learn about our commercial Adverse Effects data.
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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
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

Purchasing individual compounds or compound libraries for your research?
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International/Other Brands
Mexoryl SX
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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 flag
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 flag
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 flag
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 flag
Anthelios Lotion Corps Ultra-fluideEcamsule (2 %) + Avobenzone (3 %) + Homosalate (10 %) + Octisalate (5 %) + Octocrylene (5 %) + Oxybenzone (6 %)CreamTopicalLaboratoires La Roche Posay Canada2017-10-24Not applicableCanada flag
Anthelios MistEcamsule (2 %) + Avobenzone (3 %) + Homosalate (10 %) + Octisalate (5 %) + Octocrylene (5 %) + Oxybenzone (6 %)AerosolTopicalLaboratoires La Roche Posay Canada2015-05-04Not applicableCanada flag
Anthelios S - Ecran Solaire SPF 30Ecamsule (2 %) + Avobenzone (2 %) + Enzacamene (5 %) + Titanium dioxide (4 %)CreamTopicalLaboratoires La Roche Posay Canada1997-05-292010-06-08Canada flag
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 flag
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 flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alkanesulfonic acid / Aromatic homopolycyclic compound / Aromatic monoterpenoid / Benzenoid / Bornane monoterpenoid / Carbonyl group / Hydrocarbon derivative / Ketone / Monocyclic benzene moiety / Organic oxide
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
M94R1PM439
CAS number
92761-26-7
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

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]
PubChem Compound
9915879
PubChem Substance
347827874
ChemSpider
28534218
RxNav
1544124
ChEBI
135830
ChEMBL
CHEMBL3989850
Wikipedia
Ecamsule

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentMelasma1
2CompletedTreatmentEpidermal p53 Expression / Solar Elastosis1
1CompletedOtherSystemic Exposure to Sunscreen Ingredients1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
AerosolTopical
SprayTopical
StickTopical
GelTopical
LotionTopical
CreamTopical
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

Drug created on November 30, 2015 12:10 / Updated on June 12, 2020 10:52

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