Ensulizole

Identification

Name
Ensulizole
Accession Number
DB11115
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Ensulizole
  • phenylbenzimidazole sulfonic acid
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Covergirl Outlast All Day Stay Fabulous 3-IN-1 FoundationEmulsionTopicalHfc Prestige International Canada Inc2012-11-13Not applicableCanada
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 805 IvoryLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 810 Classic IvoryLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 820 Creamy NaturalLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 825 Buff BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 832 Nude BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 840 Natural BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 842 Medium BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 845 Warm BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 850 Creamy BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
15 SPF Fps Premium SunscreenEnsulizole (2.0 %) + Avobenzone (3.0 %) + Octocrylene (10.0 %) + Oxybenzone (2.0 %)LotionTopicalEmpack Spraytech Inc.2005-05-04Not applicableCanada
45 SPF Sunscreen SprayEnsulizole (1.0 %) + Avobenzone (3.0 %) + Homosalate (10.0 %) + Octisalate (5.0 %) + Octocrylene (2.5 %) + Oxybenzone (4.0 %)SprayTopicalPrime Enterprises, Inc.2008-05-082015-07-20Canada
Absolute Oil Control FoundationEnsulizole (3 %) + Zinc oxide (2.94 %)LiquidTopicalAccess Business Group1999-06-012010-07-09Canada
ac care Bees Sun Protection Broad Spectrum SPF 50Ensulizole (39 mg/1g) + Octinoxate (74 mg/1g) + Octocrylene (30 mg/1g) + Titanium dioxide (49 mg/1g) + Zinc oxide (49 mg/1g)CreamTopicalDong Sung Bio Pharm. Co., Ltd.2017-01-16Not applicableUs
Advanced Firming and Anti WrinkleEnsulizole (2 g/100g) + Octinoxate (7.5 g/100g)CreamTopicalWalgreen2011-02-012012-12-01Us
Advanced Firming and Anti WrinkleEnsulizole (2 g/100g) + Octinoxate (7.5 g/100g)CreamTopicalRite Aid2010-02-10Not applicableUs
Advanced Revitalift DayEnsulizole (1.7 %) + Octinoxate (7.5 %)CreamTopicalL'oreal2006-08-082008-07-23Canada
Advanced Revitalift DayEnsulizole (2 %) + Octinoxate (7.5 %)CreamTopicalL'oreal2007-12-152019-06-06Canada
Advanced Revitalift LotionEnsulizole (1.8 %) + Octinoxate (7.5 %)LotionTopicalL'oreal2006-08-082008-09-11Canada
Advanced Revitalift Lotion SPF 15Ensulizole (1.8 %) + Octinoxate (7.5 %)LotionTopicalL'oreal2011-03-142012-08-03Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Skinprint Ultra Sheer SPF 20Ensulizole (3 g/100g) + Avobenzone (1.5 g/100g) + Octinoxate (6 g/100g) + Octocrylene (1.2 g/100g)LotionTopicalThe Skin Atelier, Inc.2009-08-06Not applicableUs
Skinprint Ultra Sheer SPF 20Ensulizole (4 g/100g) + Avobenzone (3 g/100g) + Homosalate (15 g/100g) + Octisalate (5 g/100g) + Octocrylene (2.7 g/100g) + Oxybenzone (5 g/100g)LotionTopicalThe Skin Atelier, Inc.2010-10-06Not applicableUs
Categories
UNII
9YQ9DI1W42
CAS number
27503-81-7
Weight
Average: 274.29
Monoisotopic: 274.041213364
Chemical Formula
C13H10N2O3S
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

Pharmacology

Indication

Indicated to be used as an UV-B-absorbing molecule in sunscreen formulations.

Pharmacodynamics

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.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Toxicity

Dermal LD50 in rat is > 3000 mg/kg and oral LD50 in rat is > 16000 mg/kg 4.

Affected organisms
Not Available
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
Not Available

References

General References
  1. 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. [PubMed:20574440]
  2. Rai R, Shanmuga SC, Srinivas C: Update on photoprotection. Indian J Dermatol. 2012 Sep;57(5):335-42. doi: 10.4103/0019-5154.100472. [PubMed:23112351]
  3. 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. [PubMed:11883597]
  4. ENSULIZOLE: material safety data sheet - Cymit Quimica, SL [Link]
External Links
PubChem Compound
33919
PubChem Substance
347827902
ChemSpider
31267
BindingDB
181124
RxNav
13714
ChEBI
135132
ChEMBL
CHEMBL1987518
ZINC
ZINC000006467621
Wikipedia
Ensulizole
AHFS Codes
  • 84:80.00 — Sunscreen Agents
MSDS
Download (62.6 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SprayTopical
SprayCutaneous
LiquidTopical0.03 mg/1mL
EmulsionTopical
JellyTopical
LiquidTopical30 mg/1mL
LiquidTopical
LiquidTopical3 g/100mL
GelTopical
LotionTopical
LiquidTopical
EmulsionTopical
LotionTopical
PowderTopical
SuspensionTopical
GelTopical
GelTopical3 g/100mL
CreamTopical
CreamTopical
KitTopical
Cream; liquidTopical
CreamCutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300, decomposes at 410 MSDS
water solubilitySolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.317 mg/mLALOGPS
logP1.03ALOGPS
logP-0.14ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)4.93ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.05 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.69 m3·mol-1ChemAxon
Polarizability27.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00di-0090000000-7987784c7869933fe7d2
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-006x-0950000000-41e7f48b728ad64e2644
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0006-0900000000-15af96954e5768106935
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-7bfcf4b4c271c9c450c9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0190000000-bf171a8f939edc704a3f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ec980d27ce16d09dfb19
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-315f70e7c22cbfa1a163
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dl-0690000000-0e948fdb1c99ee63de22
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dl-0790000000-50f2eb115b89406ee8c4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-293262bfb0afdd3c114a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0190000000-00d18a90bdaa92bd1855
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0900000000-f2465c2ecb95ddaf72a5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0390000000-5d983cc9b05c5366df7d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0910000000-7671f7a47a45dc44b67f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0007-0930000000-6e6b736bceb36ed18921
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0007-0910000000-127cca6ef93f3abc9dd9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0190000000-b10c1e57fd2019bc18c7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-0190000000-2ed12c0d409c45ff98a1

Taxonomy

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
Phenylbenzimidazole / 2-phenylimidazole / Arylsulfonic acid or derivatives / 1-sulfo,2-unsubstituted aromatic compound / Monocyclic benzene moiety / Benzenoid / Azole / Imidazole / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on December 03, 2015 09:51 / Updated on April 09, 2020 00:17

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