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Also known as: 155633-54-8, Silatrizole, Mexoryl xl, Drometrizole trisiloxane [inci], Drometrizole trisiloxane [who-dd], 2-(benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[methyl-bis(trimethylsilyloxy)silyl]propyl]phenol
Molecular Formula
C24H39N3O3Si3
Molecular Weight
501.8  g/mol
InChI Key
HUVYTMDMDZRHBN-UHFFFAOYSA-N
FDA UNII
HC22845I1X

CAS 155633-54-8
Drometrizole trisiloxane is a photostable UVA and UVB light filter. The compound is a lipophilic benzotriazole derivative marketed as Meroxyl XL by L'Oreal, although sunscreens with drometrizole trisiloxane are currently only approved for use in the EU, Canada, Australia, and Japan, among other countries. Despite being used elsewhere in the world with relatively few reports of adverse reactions, the FDA continues to cite that the existing scientific record is not sufficient to establish the compound as being generally recognized as safe and effective for over-the-counter sunscreen use.
1 2D Structure

CAS 155633-54-8

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[methyl-bis(trimethylsilyloxy)silyl]propyl]phenol
2.1.2 InChI
InChI=1S/C24H39N3O3Si3/c1-18-14-20(15-19(2)17-33(9,29-31(3,4)5)30-32(6,7)8)24(28)23(16-18)27-25-21-12-10-11-13-22(21)26-27/h10-14,16,19,28H,15,17H2,1-9H3
2.1.3 InChI Key
HUVYTMDMDZRHBN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=C(C(=C1)N2N=C3C=CC=CC3=N2)O)CC(C)C[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C
2.2 Other Identifiers
2.2.1 UNII
HC22845I1X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Mexoryl Xl

2. Silatrizole

2.3.2 Depositor-Supplied Synonyms

1. 155633-54-8

2. Silatrizole

3. Mexoryl Xl

4. Drometrizole Trisiloxane [inci]

5. Drometrizole Trisiloxane [who-dd]

6. 2-(benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[methyl-bis(trimethylsilyloxy)silyl]propyl]phenol

7. Or 10154

8. Or-10154

9. Hc22845i1x

10. Phenol, 2-(2h-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3-(1,3,3,3-tetramethyl-1-((trimethylsilyl)oxy)-1-disiloxanyl)propyl)-

11. Phenol, 2-(2h-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3-(1,3,3,3-tetramethyl-1-((trimethylsilyl)oxy)disiloxanyl)propyl)-

12. 2-(2h-benzo[d][1,2,3]triazol-2-yl)-6-(3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)-2-methylpropyl)-4-methylphenol

13. Phenol, 2-(2h-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]-1-disiloxanyl]propyl]-

14. Unii-hc22845i1x

15. Mexoryl Xl;silatrizole

16. Schembl15380

17. Amy224

18. Dtxsid40431753

19. Act12435

20. Bcp28866

21. Db11585

22. Drometrizole Trisiloxane [usp-rs]

23. Ncgc00532508-01

24. Db-091411

25. Drometrizole Trisiloxane, Analytical Standard

26. Q5308268

27. Drometrizole Trisiloxane, United States Pharmacopeia (usp) Reference Standard

28. 2-(2h-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3-(1,3,3,3-tetramethyl-1-(trimethylsilyloxy)-disiloxanyl)propyl)phenol

29. 320341-73-9

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 501.8 g/mol
Molecular Formula C24H39N3O3Si3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count9
Exact Mass501.22992172 g/mol
Monoisotopic Mass501.22992172 g/mol
Topological Polar Surface Area69.4 Ų
Heavy Atom Count33
Formal Charge0
Complexity613
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Drometrizole trisiloxane is used as an active ingredient in various sunscreens for the indication of protecting the skin by absorbing the damaging UV radiation of sunlight.


5 Pharmacology and Biochemistry
5.1 Pharmacology

As an active ingredient in sunscreen products, drometrizole trisiloxane is applied directly onto human skin where it acts as a chemical sunscreen layer between skin and sunlight that also directly absorbs the UV sunlight radiation. Since drometrizole trisiloxane is also considered to have little to no absorption through the skin, little systemic exposure and pharmacokinetics are expected and users can freely wash off and re-apply the compound as necessary.


5.2 Absorption, Distribution and Excretion

Absorption

Drometrizole trisiloxane is reported as having little to no absorption through the skin. 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. Despite the extensive use of sunscreen products around the world, there have been few reports of adverse effects related to their use.


Route of Elimination

Drometrizole trisiloxane is reported as having little to no absorption through the skin. The systemic presence of the compound is consequently expected to be minimal.


Volume of Distribution

Drometrizole trisiloxane is reported as having little to no absorption through the skin. The systemic presence of the compound is consequently expected to be minimal.


Clearance

Drometrizole trisiloxane is reported as having little to no absorption through the skin. The systemic presence of the compound is consequently expected to be minimal.


5.3 Metabolism/Metabolites

Drometrizole trisiloxane is reported as having little to no absorption through the skin. The systemic presence of the compound is consequently expected to be minimal.


5.4 Biological Half-Life

Drometrizole trisiloxane is reported as having little to no absorption through the skin. The systemic presence of the compound is consequently expected to be minimal.


5.5 Mechanism of Action

Ultraviolet radiation is the invisible energy component to sunlight and consists of three wavelength ranges: (a) UVA is long-range UV radiation between 320-400nm. Although not as energetic as UVB, UVA can penetrate deep into the dermis. UVA can cause immediate tanning, premature skin aging, and can also play a role in the formation of some skin cancers. Approximately 95% of UVA from the sun passes through Earth's ozone layer. (b) UVB is short-wavelength UV radiation between 280-320nm. It is capable of penetrating the outer protective layer of the skin and is responsible for delayed tanning, sunburns, and most skin cancers. A large amount of UVB is absorbed by the ozone layer, however, as only 5% reaches the Earth's surface. (c) UVC is comprised of wavelengths between 100-280nm and is very energetic. It is very dangerous to all forms of life, even when the exposure is short. However, UVC radiation is generally filtered out by the ozone layer and never reaches the Earth. Ultimately, the shorter the wavelength, the more harmful the UV radiation - although shorter wavelength UV radiation is less able to penetrate the skin. Subsequently, drometrizole trisiloxane is a broad spectrum lipophilic benzotriazole derivative chemical sunscreen that is capable of absorbing UVA and UVB radiation. It is also photostable, meaning that it will not degrade in the presence of sunlight, unlike other UV filters like the widely used UVA absorber avobenzone. When combined with the UV blocker ecamsule, it has been shown that the two UV blockers elicit a synergistic effect involving an enhanced protective action for the skin against UVA and UVB radiation. Additionally, drometrizole trisiloxane is usually combined with other active sunscreen agents like titanium dioxide, avobenzone, and others to ensure the combined product covers or protects against as broad a spectrum of UV radiation as possible, considering drometrizole trisiloxane does not absorb against the entire range of UV radiation. And finally, at the molecular level, it is believed that the general structure of various UV blockers like drometrizole trisiloxane as aromatic molecules conjugated with carbonyl groups is capable of absorbing high energy ultraviolet rays and then consequently releasing that energy as less harmful, lower energy rays.


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