Identification
- Summary
Ecamsule is a sunscreen agent found in sunscreens that absorbs UV rays.
- Generic Name
- Ecamsule
- DrugBank Accession Number
- DB09534
- Background
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
Structure for Ecamsule (DB09534)
- 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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for prophylaxis of Sunburn ••• ••• - Contraindications & Blackbox Warnings
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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
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The most common reactions were dermatitis, dry skin, acne, itching, redness and skin discomfort.
- 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.- International/Other Brands
- Mexoryl SX
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 45 SPF High Protection Uva Uvb Cream Ecamsule (2.0 %) + Avobenzone (3.5 %) + Drometrizole trisiloxane (3.0 %) + Octocrylene (10 %) + Titanium dioxide (3.3 %) Cream Topical Laboratoires La Roche Posay Canada 2008-04-16 2016-08-31 Canada 
Anthelios - Lait SPF 45 Ecamsule (3.0 %) + Avobenzone (2.0 %) + Octocrylene (10.0 %) + Titanium dioxide (3.7 %) Lotion Topical Laboratoires La Roche Posay Canada 2004-05-01 2008-06-20 Canada Anthelios 50+ Ecamsule (0.5 % w/w) + Avobenzone (5 % w/w) + Bemotrizinol (6 % w/w) + Drometrizole trisiloxane (4 % w/w) + Homosalate (10 % w/w) + Octisalate (5 % w/w) + Titanium dioxide (2.5 % w/w) Lotion Topical Laboratoires La Roche Posay Canada Not applicable Not applicable Canada Anthelios Age Correct Ecamsule (1 % w/w) + Avobenzone (2.3 % w/w) + Bemotrizinol (3.8 % w/w) + Drometrizole trisiloxane (1.3 % w/w) + Ensulizole (3.5 % w/w) + Octisalate (5 % w/w) Cream Topical Laboratoires La Roche Posay Canada 2023-05-01 Not applicable Canada Anthelios Dermo-kids Ecamsule (1.5 % w/w) + Avobenzone (3 % w/w) + Drometrizole trisiloxane (4.5 % w/w) + Octisalate (5 % w/w) + Octocrylene (2.5 % w/w) + Titanium dioxide (5.85 % w/w) Lotion Topical Laboratoires La Roche Posay Canada 2015-05-04 Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image P.CALM Water Barrier Suncream Ecamsule (26.4 mg/1mL) + Bemotrizinol (5 mg/1mL) + Diethylamino hydroxybenzoyl hexyl benzoate (10 mg/1mL) + Octyl triazone (27 mg/1mL) + Polysilicone-15 (10 mg/1mL) Cream Topical LIFE WITH CORPORATION Inc. 2023-10-17 Not applicable US 
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
- Affected organisms
- Humans and other mammals
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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Melasma 1 2 Completed Treatment Epidermal p53 Expression / Solar Elastosis 1 1 Completed Other Systemic Exposure to Sunscreen Ingredients 1 Not Available Completed Diagnostic Dermatitis, Photocontact 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Aerosol Topical Spray Topical Stick Topical Gel Topical Lotion Topical Cream Topical Emulsion Topical Liquid Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00571 mg/mL ALOGPS logP 0.37 ALOGPS logP 4.1 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) -1 Chemaxon pKa (Strongest Basic) -5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 142.88 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 143.56 m3·mol-1 Chemaxon Polarizability 59.64 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 232.21297 predictedDeepCCS 1.0 (2019) [M+H]+ 234.40163 predictedDeepCCS 1.0 (2019) [M+Na]+ 240.31493 predictedDeepCCS 1.0 (2019)
Drug created at November 30, 2015 19:10 / Updated at February 21, 2021 18:52