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
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.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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.

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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

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 regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Covergirl Outlast All Day Stay Fabulous 3-IN-1 FoundationEmulsion3 % w/wTopicalHfc Prestige International Canada Inc2012-11-132021-01-01Canada flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 805 IvoryLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 810 Classic IvoryLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 820 Creamy NaturalLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 825 Buff BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 832 Nude BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 840 Natural BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 842 Medium BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 845 Warm BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Covergirl Outlast Stay Fabulous 3in1 Foundation Broad spectrum SPF 20 - 850 Creamy BeigeLiquid0.03 mg/1mLTopicalNoxell2012-06-25Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
15 SPF Fps Premium SunscreenEnsulizole (2 % w/w) + Avobenzone (3 % w/w) + Octocrylene (10 % w/w) + Oxybenzone (2 % w/w)LotionTopicalEmpack Spraytech Inc2005-05-042021-08-10Canada flag
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 flag
Absolute Oil Control FoundationEnsulizole (3 %) + Zinc oxide (2.94 %)LiquidTopicalAccess Business Group1999-06-012010-07-09Canada flag
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)CreamTopicalOmar Sharif Cosmetic Co., Ltd.2017-01-16Not applicableUS flag
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)CreamTopicalDongSung Pharm Co., Ltd.2017-01-16Not applicableUS flag
Advanced Firming and Anti WrinkleEnsulizole (2 g/100g) + Octinoxate (7.5 g/100g)CreamTopicalWalgreen2011-02-012012-12-01US flag
Advanced Firming and Anti WrinkleEnsulizole (2 g/100g) + Octinoxate (7.5 g/100g)CreamTopicalRite Aid2010-02-10Not applicableUS flag
Advanced Revitalift DayEnsulizole (1.7 %) + Octinoxate (7.5 %)CreamTopicalL'oreal2006-08-082008-07-23Canada flag
Advanced Revitalift DayEnsulizole (2 %) + Octinoxate (7.5 %)CreamTopicalL'oreal2007-12-152019-06-06Canada flag
Advanced Revitalift LotionEnsulizole (1.8 %) + Octinoxate (7.5 %)LotionTopicalL'oreal2006-08-082008-09-11Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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.2009-08-062019-10-11US flag
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.2010-10-062019-10-11US flag

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
  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. [Article]
  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. [Article]
  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. [Article]
  4. ENSULIZOLE: material safety data sheet - Cymit Quimica, SL [Link]
PubChem Compound
33919
PubChem Substance
347827902
ChemSpider
31267
BindingDB
181124
RxNav
13714
ChEBI
135132
ChEMBL
CHEMBL1987518
ZINC
ZINC000006467621
Wikipedia
Ensulizole
MSDS
Download (62.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SprayTopical
SprayCutaneous
EmulsionTopical3 % w/w
LiquidTopical0.03 mg/1mL
EmulsionTopical3 %
JellyTopical40 mg / g
LiquidTopical30 mg/1mL
LiquidTopical3.2 % w/w
LiquidTopical3 g/100mL
GelTopical1 %
LotionTopical1 %
LiquidTopical36 mg/1mL
LiquidTopical35 mg/1mL
LiquidTopical
EmulsionTopical
LotionTopical
PowderTopical
SuspensionTopical
GelTopical
GelTopical3 g/100mL
CreamTopical3.5 %
GelTopical4 %
CreamTopical
SprayTopical39.12 mg/1mL
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

Drug created at December 03, 2015 16:51 / Updated at September 29, 2022 07:52