Ethylhexyl methoxycrylene

Identification

Generic Name

DrugBank Accession Number

DB11226

Background

Ethylhexyl methoxycrylene is a photostabilizer that preserves the effectiveness of UV filters by interacting with both the singlet and triplet states ⁶. It returns UV filters to their ground states without absorbing sunlight ⁶. It is used as a solvent for crystalline UV filters and is easily emulsified and suitable for use in various lotions, creams, sprays, sticks, and gel formulations ⁶. It currently enjoys regional approvals in Canada, the EU, and the US ³.

Type

Small Molecule

Groups

Approved, Experimental

Structure

Similar Structures

Weight: Average: 391.511
Monoisotopic: 391.214743798
Chemical Formula: C₂₅H₂₉NO₃

Synonyms

Not Available

External IDs

RX-14180

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Pharmacology

Indication

Ethylhexyl methoxycrylene is employed as a photostabilizing agent in various sunscreen products ³.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to prevent	Sunburn		••• •••

Contraindications & Blackbox Warnings

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Pharmacodynamics

As an active ingredient in topical sunscreen products, ethylhexyl methoxycrylene is applied directly onto human skin where it acts as a critical component for conferring photostability to the product's other constituent ingredients, protecting the product as a whole from deterioration in the sunlight ³. Additionally, considering the high log Pow value (6.05-6.32) and low water solubility, dermal absorption of ethylhexyl methoxycrylene is expected to be low. This is supported by a dermal absorption of less than 5% observed for an acceptable analogue of the notified chemical ⁴. Consequently, little systemic exposure and pharmacokinetics are expected and users can freely wash off and re-apply ethylhexyl methoxycrylene containing compounds as necessary.

Mechanism of action

Ethylhexyl methoxycrylene is a photostabilizer with exceptionally low singlet (S1) and triplet (T1) energy states ¹. Given these properties, ethylhexyl methoxycrylene is capable of draining the singlet excited state reservoir of UV radiation excited molecules of various sunscreen agents ⁵. This action used to be considered impossible because molecules stay in the singlet excited state for a very short period of time - often as short as 13 one-thousandths of a billionth of a second ⁵. Ethylhexyl methoxycrylene, however, is a singlet quencher that dramatically reduces the flow of energy to the triplet escited state reservoir ⁵. As it quenches the singlet excited state, molecules do not have the chance to get to the triplet excited state reservoir and largely return to the ground state where they can continue functioning ⁵. In fact, this mechanism of action of ethylhexyl methoxycrylene is considered as being able to return UV filters to their ground states without absorbing sunlight ⁶.

Ultimately, because ethylhexyl methoxycrylene can work so quickly, it allows manufacturers to formulate products with combinations of sunscreen ingredients that used to be considered too photo-unstable to be effective ⁵. Moreover, ethylhexyl methoxycrylene is easily emulsified, and is suitable for use in lotions, creams, sprays, sticks, and gel formulations ⁶.

Absorption

Ethylhexyl methoxycrylene is reported as having little to no absorption through the skin ⁴. At this time, however, studies demonstrate that the components of most commonly used sunscreens are likely absorbed into the skin at least to some extent - although penetration to deeper tissues and the cutaneous circulation remains limited ². Despite the extensive use of sunscreen products around the world, there have been few reports of adverse effects related to their use ².

Volume of distribution