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Identification
- Summary
Ensulizole is an ingredient used in sunscreens to absorb UVB radiation.
- Brand Names
- Eucerin
- Generic Name
- Ensulizole
- DrugBank Accession Number
- DB11115
- Background
Ensulizole, also known as 2-phenylbenzimidazole-5-sulfonic acid, is a water-soluble sunscreen agent that absorbs strongly at UV-B wavelengths. It is commonly found in cosmetic products and sunscreen formulas in combination with other UV filter compounds due to its minimal protection against UV-A wavelengths. Due to its water solubility, ensulizole is commonly used in products formulated to feel light and less oily 2. It was demonstrated by studies that ensulizole treatment provided protection against cyclobutane pyrimidine dimers and photosensitized the formation of oxidized guanine bases after UV-A or UV-B exposure 1. According to the FDA, the maximal approved concentration of ensulizole is 148 mM although concentrations ranging between 74 and 148mM can be found in commercial sunscreen products 1.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ensulizole (DB11115)
- Weight
- Average: 274.29
Monoisotopic: 274.041213364 - Chemical Formula
- C13H10N2O3S
- Synonyms
- Ensulizole
- phenylbenzimidazole sulfonic acid
Pharmacology
- Indication
Indicated to be used as an UV-B-absorbing molecule in sunscreen formulations.
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Ensulizole is a selective UV-B filter with little activity against UV-A wavelengths. In vitro, ensulizole oxidizes guanine bases upon photoexcitation by UV-B and may cause photodamage on DNA, proteins and lipids in the cellular context 1.
- Mechanism of action
Ensulizole strongly absorbs UV-B wavelengths. It offers protection against UV-B-induced cyclobutane pyrimidine dimers 1. Based on the findings in vitro and in cellulo, ensulizole induces damage on the DNA, causes DNA strand breaks and photosensitizes the formation of oxidized guanines via type I and II photosensitization mechanisms following UV-A or UV-B irradiation 1. Ensulizole is capable of generating reactive oxygen species, including singlet oxygen upon photoexcitation 1.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Dermal LD50 in rat is > 3000 mg/kg and oral LD50 in rat is > 16000 mg/kg 4.
- 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.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Covergirl Outlast All Day Stay Fabulous 3-IN-1 Foundation Emulsion 3 % w/w Topical Hfc Prestige International Canada Inc 2012-11-13 2021-01-01 Canada 
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 805 Ivory Liquid 0.03 mg/1mL Topical Noxell 2012-06-25 Not applicable US 
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 810 Classic Ivory Liquid 0.03 mg/1mL Topical Noxell 2012-06-25 Not applicable US Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 820 Creamy Natural Liquid 0.03 mg/1mL Topical Noxell 2012-06-25 Not applicable US Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 825 Buff Beige Liquid 0.03 mg/1mL Topical Noxell 2012-06-25 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 15 SPF Fps Premium Sunscreen Ensulizole (2 % w/w) + Avobenzone (3 % w/w) + Octocrylene (10 % w/w) + Oxybenzone (2 % w/w) Lotion Topical Empack Spraytech Inc 2005-05-04 2021-08-10 Canada 45 SPF Sunscreen Spray Ensulizole (1.0 %) + Avobenzone (3.0 %) + Homosalate (10.0 %) + Octisalate (5.0 %) + Octocrylene (2.5 %) + Oxybenzone (4.0 %) Spray Topical Prime Enterprises, Inc. 2008-05-08 2015-07-20 Canada Absolute Oil Control Foundation Ensulizole (3 %) + Zinc oxide (2.94 %) Liquid Topical Access Business Group 1999-06-01 2010-07-09 Canada ac care Bees Sun Protection Broad Spectrum SPF 50 Ensulizole (39 mg/1g) + Octinoxate (74 mg/1g) + Octocrylene (30 mg/1g) + Titanium dioxide (49 mg/1g) + Zinc oxide (49 mg/1g) Cream Topical DongSung Pharm Co., Ltd. 2017-01-16 Not applicable US ac care Bees Sun Protection Broad Spectrum SPF 50 Ensulizole (39 mg/1g) + Octinoxate (74 mg/1g) + Octocrylene (30 mg/1g) + Titanium dioxide (49 mg/1g) + Zinc oxide (49 mg/1g) Cream Topical Omar Sharif Cosmetic Co., Ltd. 2017-01-16 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dr.Jucre Rebirth White Sun Protection Ensulizole (3.50 g/100mL) + Adenosine (0.04 g/100mL) + Avobenzone (4.00 g/100mL) + Bemotrizinol (1.50 g/100mL) + Homosalate (6.00 g/100mL) + Nicotinamide (2.00 g/100mL) + Octinoxate (7.30 g/100mL) + Octisalate (4.50 g/100mL) + Octocrylene (2.00 g/100mL) Cream Topical NATURECELL CO., LTD. 2022-10-01 Not applicable US Skinprint Ultra Sheer SPF 20 Ensulizole (3 g/100g) + Avobenzone (1.5 g/100g) + Octinoxate (6 g/100g) + Octocrylene (1.2 g/100g) Lotion Topical The Skin Atelier, Inc. 2009-08-06 2019-10-11 US Skinprint Ultra Sheer SPF 20 Ensulizole (4 g/100g) + Avobenzone (3 g/100g) + Homosalate (15 g/100g) + Octisalate (5 g/100g) + Octocrylene (2.7 g/100g) + Oxybenzone (5 g/100g) Lotion Topical The Skin Atelier, Inc. 2010-10-06 2019-10-11 US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylbenzimidazoles. These are compounds containing a phenylbenzimidazole skeleton, which consists of a benzimidazole moiety where its imidazole ring is attached to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzimidazoles
- Sub Class
- Phenylbenzimidazoles
- Direct Parent
- Phenylbenzimidazoles
- Alternative Parents
- Phenylimidazoles / 1-sulfo,2-unsubstituted aromatic compounds / Benzene and substituted derivatives / Sulfonyls / Organosulfonic acids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 1 more
- Substituents
- 1-sulfo,2-unsubstituted aromatic compound / 2-phenylimidazole / Aromatic heteropolycyclic compound / Arylsulfonic acid or derivatives / Azacycle / Azole / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Imidazole show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9YQ9DI1W42
- CAS number
- 27503-81-7
- InChI Key
- UVCJGUGAGLDPAA-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H10N2O3S/c16-19(17,18)10-6-7-11-12(8-10)15-13(14-11)9-4-2-1-3-5-9/h1-8H,(H,14,15)(H,16,17,18)
- IUPAC Name
- 2-phenyl-1H-1,3-benzodiazole-6-sulfonic acid
- SMILES
- OS(=O)(=O)C1=CC2=C(C=C1)N=C(N2)C1=CC=CC=C1
References
- General References
- Bastien N, Millau JF, Rouabhia M, Davies RJ, Drouin R: The sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid photosensitizes the formation of oxidized guanines in cellulo after UV-A or UV-B exposure. J Invest Dermatol. 2010 Oct;130(10):2463-71. doi: 10.1038/jid.2010.150. Epub 2010 Jun 24. [Article]
- Rai R, Shanmuga SC, Srinivas C: Update on photoprotection. Indian J Dermatol. 2012 Sep;57(5):335-42. doi: 10.4103/0019-5154.100472. [Article]
- Inbaraj JJ, Bilski P, Chignell CF: Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic acid. Photochem Photobiol. 2002 Feb;75(2):107-16. [Article]
- ENSULIZOLE: material safety data sheet - Cymit Quimica, SL [Link]
- External Links
- PubChem Compound
- 33919
- PubChem Substance
- 347827902
- ChemSpider
- 31267
- BindingDB
- 181124
- 13714
- ChEBI
- 135132
- ChEMBL
- CHEMBL1987518
- ZINC
- ZINC000006467621
- Wikipedia
- Ensulizole
- MSDS
- Download (62.6 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Spray Topical Spray Cutaneous Emulsion Topical 3 % w/w Liquid Topical 0.03 mg/1mL Emulsion Topical 3 % Jelly Topical 40 mg / g Liquid Topical 30 mg/1mL Liquid Topical 3.2 % w/w Liquid Topical 3 g/100mL Gel Topical 1 % Lotion Topical 1 % Liquid Topical 36 mg/1mL Liquid Topical 35 mg/1mL Liquid Topical Emulsion Topical Lotion Topical Powder Topical Suspension Topical Liquid Topical 27 mg/1mL Gel Topical Gel Topical 3 g/100mL Cream Topical 3.5 % Gel Topical 4 % Cream Topical Spray Topical 39.12 mg/1mL Kit Topical Cream; liquid Topical Cream Cutaneous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >300, decomposes at 410 MSDS water solubility Soluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.317 mg/mL ALOGPS logP 1.03 ALOGPS logP -0.14 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) -2.2 Chemaxon pKa (Strongest Basic) 4.93 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 83.05 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 80.69 m3·mol-1 Chemaxon Polarizability 27.73 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No 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]- 173.0522191 predictedDarkChem Lite v0.1.0 [M-H]- 160.64775 predictedDeepCCS 1.0 (2019) [M+H]+ 173.0680191 predictedDarkChem Lite v0.1.0 [M+H]+ 163.00584 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.4339191 predictedDarkChem Lite v0.1.0 [M+Na]+ 169.46239 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at September 07, 2024 14:25