ENSULIZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10N2O3S
Molecular Weight	274.295
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)C1=CC2=C(C=C1)N=C(N2)C3=CC=CC=C3

InChI

InChIKey=UVCJGUGAGLDPAA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=611798eb-4004-40e8-b7ff-345136253975
Curator's Comment: description was created based on several sources, including: http://www.ncbi.nlm.nih.gov/pubmed/23112351

Ensulizole (INN) (phenylbenzimidazole sulfonic acid) is a common sunscreen agent. In 1999, the United States Food and Drug Administration regulated that the name ensulizole be used on sunscreen labels in the United States. It is a selective UVB filter, allowing almost all UVA transmission. The scope of UVB is 290 to 340 nanometers whereas the UVA range is 320 to 400 nanometers. For better UVA protection, it must be paired with avobenzone, titanium dioxide, or zinc oxide; outside of the United States it can also be paired with a UV absorber of the Tinosorb or Mexoryl types. Because is water-soluble, it has the characteristic of feeling lighter on skin. As such, it is often used in sunscreen lotions or moisturizers whose aesthetic goal is a non-greasy finish. The free acid is poorly soluble in water, so it is only used as its soluble salts

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ultraviolet B 3 Target ID: ultraviolet B Sources: http://www.ncbi.nlm.nih.gov/pubmed/23112351	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sunburn 84 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=611798eb-4004-40e8-b7ff-345136253975	Preventing		Approved 8583	ALOE SUNSCREEN Approved Use Unknown Launch Date 2011

Doses

Dose	Population	Adverse events
10 % single, topical Studied dose Dose: 10 % Route: topical Route: single Dose: 10 % Sources: https://pubmed.ncbi.nlm.nih.gov/30891767/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30891767/	Disc. AE: Allergic contact dermatitis... AEs leading to discontinuation/dose reduction: Allergic contact dermatitis (100%) Sources: https://pubmed.ncbi.nlm.nih.gov/30891767/

AEs

AE	Significance	Dose	Population
Allergic contact dermatitis	100% Disc. AE	10 % single, topical Studied dose Dose: 10 % Route: topical Route: single Dose: 10 % Sources: https://pubmed.ncbi.nlm.nih.gov/30891767/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30891767/

PubMed

Title	Date	PubMed
Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic acid.	2002 Feb	11883597
Sensitive sequential-injection system for the determination of 2-phenylbenzimidazole-5-sulphonic acid in human urine samples using on-line solid-phase extraction coupled with fluorimetric detection.	2003 Mar 1	18968944
Multiclass determination of sunscreen chemicals in water samples by liquid chromatography-tandem mass spectrometry.	2008 Feb 15	18217772
The sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid photosensitizes the formation of oxidized guanines in cellulo after UV-A or UV-B exposure.	2010 Oct	20574440

Patents

Sample Use Guides

In Vivo Use Guide

apply liberally 15 minutes before sun exposure

Route of Administration: Topical

In Vitro Use Guide

Unknown

Name

Type

Language

PHENYLBENZIMIDAZOLE SULFONIC ACID

Preferred Name

English

ENSULIZOLE

Official Name

English

2-Phenylbenzimidazole-5-sulfonic acid

Systematic Name

English

ENSULIZOLE [MI]

Common Name

English

Ensulizole [WHO-DD]

Common Name

English

2-PHENYLBENZIMIDAZOLE-5-SULFONIC ACID [VANDF]

Common Name

English

ENSULIZOLE [USAN]

Common Name

English

1H-BENZIMIDAZOLE-5-SULFONIC ACID-2-PHENYL-

Common Name

English

ensulizole [INN]

Common Name

English

ENSULIZOLE [USP-RS]

Common Name

English

ENSULIZOLE [USP MONOGRAPH]

Common Name

English

ENSULIZOLE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C851