Identification
- Summary
Sulisobenzone is an ingredient used in sunscreen to block UVA and UVB radiation.
- Generic Name
- Sulisobenzone
- DrugBank Accession Number
- DB11185
- Background
Sulisobenzone is approved by the FDA in concentrations of up to 10% and in Canada, is approved by Health Canada at the same concentrations 14. It works to filter out both UVA and UVB rays, protecting the skin from sun UV damage 8.
The UV-filter substance, sulisobenzone (BP-4) is widely used an ingredient in sunscreens and other personal care products 1, 10. It falls under the drug category of benzophenones. The benzophenones are a group of aromatic ketones that have both pharmaceutical and industrial applications 13. Benzophenones may be found organically in fruits such as grapes 11.
Benzophenones are used as photoinitiators, fragrance enhancers, ultraviolet curing agents, and, occasionally, as flavor ingredients; they are also used in the manufacture of insecticides, agricultural chemicals, and pharmaceuticals and as an additive for plastics, coatings, and adhesives 12.
As a group, benzophenones may be used to delay photodegradation or extend shelf life in toiletries and plastic surface coatings 13.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Sulisobenzone (DB11185)
- Weight
- Average: 308.3
Monoisotopic: 308.03545928 - Chemical Formula
- C14H12O6S
- Synonyms
- 2-benzoyl-5-methoxy-1-phenol-4-sulfonic acid
- 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid
- 3-benzoyl-4-hydroxy-6-methoxybenzenesulfonic acid
- 5-benzoyl-4-hydroxy-2-methoxybenzenesulfonic acid
- Benzophenone-4
- Sulfisobenzone
- Sulisobenzone
- External IDs
- NSC-60584
Pharmacology
- Indication
Sunscreening agents are used to prevent sunburn, actinic keratosis, and premature skin aging and to reduce the incidence of skin cancer 5.
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- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons) 5. Correct use of sunscreens serves to reduce the risk of sunburn. Sunscreen agents prevent the occurrence of squamous-cell carcinoma of the skin when used mainly during unintentional sun exposure. No conclusion can be drawn about the cancer-preventive activity of topical use of sunscreens against both basal-cell carcinoma and cutaneous melanoma. Use of sunscreens can extend the duration of intentional sun exposure, such as bathing in the sun 6.
- Mechanism of action
A surface coating of benzophenones decreases the amount of UV radiation absorbed by the skin by limiting the total amount of energy that reaches the skin 4.
Benzophenone sunscreens, applied topically, protect the skin from these harmful effects of ultraviolet light by chemically absorbing light energy (photons). As this occurs, the benzophenone molecule becomes activated to higher energy levels. As the excited molecule returns to its ground state, the energy is released in the form of thermal energy. The hydroxyl group in the ortho position to the carbonyl group is believed to be a structural requirement for the benzophenones' absorption of UV light. This structural arrangement also contributes to the electronic stability of the molecule. Benzophenones absorb energy throughout the UV range, although the maximum UV absorbance is between 284 and 287 nm for the 2-hydroxybenzophenones 11.
Target Actions Organism ASkin epithelial cells protectorHumans - Absorption
Does not penetrate the skin to a large degree, but enhances the ability of other chemicals to penetrate 6.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol. A small amount (1%) is converted to p-hydroxybenzophenone following oral administration to rats 4.
- Route of elimination
This drug's main metabolite is excreted in urine conjugated with glucuronic acid. No p-hydroxybenzohydrol was detected in urine or feces, in a study of pharmacokinetics in rats 4.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Acute oral toxicity (LD50): 3530 mg/kg [Rat].
This drug can cause skin and eye irritation 6.
Drug-induced phototoxicity is a non-immunological inflammatory skin reaction, caused by concurrent topical or systemic exposure to a specific molecule and ultraviolet radiation. Most of the phototoxic compounds absorb energy particularly from UVA light leading to activated derivatives, which can induce cellular damage 5.
Benzophenones are ultraviolet light filters that have been documented to cause a variety of adverse skin reactions, including contact and photocontact dermatitis, contact and photocontact urticaria, and anaphylaxis. Recently, they have become especially well known for their ability to induce allergy and photoallergy. Topical sunscreens and other cosmetics are the sources of these allergens in the majority of patients, however reports of reactions secondary to use of industrial products also exist. Benzophenones as a group have been named the American Contact Dermatitis Society's Allergen of the Year for 2014 to raise awareness of both allergy and photoallergy to these ubiquitous agents 3.
The liver is the main target organ of benzophenone toxicity in rats and mice, based on elevations n liver weights, hepatocellular hypertrophy, clinical chemistry changes, and induction of liver microsomal cytochrome P450 2B isomer. The kidney was also identified as a target organ of benzophenone toxicity in rats only, which was based on exposure concentration-related increases in kidney weights and microscopic changes 15.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareTenofovir alafenamide The serum concentration of Tenofovir alafenamide can be increased when it is combined with Sulisobenzone. - 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.- Product Ingredients
Ingredient UNII CAS InChI Key Benzophenone-5 853Z42ZYAS 6628-37-1 KJCLYACXIWMFCC-UHFFFAOYSA-M - International/Other Brands
- Escalol 577 / MS 40 / Seesorb 101S / Spectra-sorb UV 284 / Sungard / Syntase 230 / Uval / Uvasorb S 5 / Uvinul D 5030 / Uvinul MS 40 / Uvinul MS-40 / Viosorb 111
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anti-frizz Sheets Swab 2 g/100g Topical NINGBO JIANGBEI OCEAN STAR TRADING CO.,LTD 2015-09-15 Not applicable US 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 3-IN-1 Active Moisturizer Sulisobenzone (0.5 % w/w) + Octinoxate (7.5 % w/w) + Oxybenzone (3.5 % w/w) Cream Topical Bb Lifestyle Canada Not applicable Not applicable Canada 
BENEFIT Triple Performing Facial Broad Spectrum SPF15 Sulisobenzone (15 mg/1mL) + Avobenzone (30 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20 mg/1mL) Cream Topical Benefit Cosmetics, LLC 2015-08-22 Not applicable US Benefit Triple Performing Facial Emulsion Broad Spectrum SPF 15 Sulisobenzone (15 mg/1mL) + Avobenzone (30 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20 mg/1mL) Emulsion Topical Benefit Cosmetics, LLC 2011-07-28 Not applicable US Brillie Ultimate Soothing Sun Shield Sulisobenzone (1.5 g/50mL) + Octinoxate (2.5 g/50mL) Cream Topical Inhanzglobal Co.,Ltd 2020-08-24 Not applicable US CD Hydra Life Pro-Youth Protective Fluid Sulisobenzone (15.0 mg/1mL) + Avobenzone (30.0 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20.0 mg/1mL) Solution Topical Parfums Christian Dior 2010-05-07 2015-03-25 US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzophenones
- Direct Parent
- Benzophenones
- Alternative Parents
- Aryl-phenylketones / Diphenylmethanes / Methoxyphenols / Benzenesulfonic acids and derivatives / 1-sulfo,2-unsubstituted aromatic compounds / Benzenesulfonyl compounds / Phenoxy compounds / Methoxybenzenes / Benzoyl derivatives / Anisoles show 7 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-sulfo,2-unsubstituted aromatic compound / Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Aryl ketone / Aryl-phenylketone / Arylsulfonic acid or derivatives / Benzenesulfonate / Benzenesulfonyl group show 20 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1W6L629B4K
- CAS number
- 4065-45-6
- InChI Key
- CXVGEDCSTKKODG-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H12O6S/c1-20-12-8-11(15)10(7-13(12)21(17,18)19)14(16)9-5-3-2-4-6-9/h2-8,15H,1H3,(H,17,18,19)
- IUPAC Name
- 5-benzoyl-4-hydroxy-2-methoxybenzene-1-sulfonic acid
- SMILES
- COC1=C(C=C(C(=O)C2=CC=CC=C2)C(O)=C1)S(O)(=O)=O
References
- General References
- Beel R, Lutke Eversloh C, Ternes TA: Biotransformation of the UV-filter sulisobenzone: challenges for the identification of transformation products. Environ Sci Technol. 2013 Jul 2;47(13):6819-28. doi: 10.1021/es400451w. Epub 2013 Jun 19. [Article]
- Seto Y, Ohtake H, Kato M, Onoue S: Phototoxic Risk Assessments on Benzophenone Derivatives: Photobiochemical Assessments and Dermal Cassette-Dosing Pharmacokinetic Study. J Pharmacol Exp Ther. 2015 Aug;354(2):195-202. doi: 10.1124/jpet.115.223644. Epub 2015 May 27. [Article]
- Heurung AR, Raju SI, Warshaw EM: Benzophenones. Dermatitis. 2014 Jan-Feb;25(1):3-10. doi: 10.1097/DER.0000000000000025. [Article]
- Sulsibenzone [Link]
- SULISOBENZONE [Link]
- SULISOBENZONE [Link]
- Sulisobezone, U.S. Pharmacopoeia Monograph [Link]
- FDA - CFR - Code of Federal Regulations Title 21: PART 352 -- SUNSCREEN DRUG PRODUCTS FOR OVER-THE-COUNTER HUMAN USE [STAYED INDEFINITELY] [Link]
- ECHA Sulisobenzone toxicity study [Link]
- Sulisobenzone, Daily Med Search [Link]
- Benzophenone [Link]
- Benzophenone, science direct [Link]
- DermNet NZ: Benzophenone Allergy [Link]
- Health Canada Monograph, Sunscreens [File]
- NTP Technical Report on the Toxicity Studies of Benzophenone [File]
- External Links
- PubChem Compound
- 19988
- PubChem Substance
- 347827937
- ChemSpider
- 18829
- 1311567
- ChEBI
- 135312
- ChEMBL
- CHEMBL2059073
- ZINC
- ZINC000001690324
- Wikipedia
- Sulisobenzone
- MSDS
- Download (148 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Swab Topical 2 g/100g Emulsion Topical Solution Topical Cream Topical Spray Topical Liquid Topical Gel Topical Lotion Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
Property Value Source melting point (°C) 145 MSDS water solubility 10 microgram/mL http://www.pharmacopeia.cn/v29240/usp29nf24s0_m80090.html - Predicted Properties
Property Value Source Water Solubility 0.214 mg/mL ALOGPS logP 0.39 ALOGPS logP 2.8 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) -2.4 Chemaxon pKa (Strongest Basic) -5 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 100.9 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 75.7 m3·mol-1 Chemaxon Polarizability 29.14 Å3 Chemaxon Number of Rings 2 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]- 180.8330183 predictedDarkChem Lite v0.1.0 [M-H]- 168.13792 predictedDeepCCS 1.0 (2019) [M+H]+ 180.9024183 predictedDarkChem Lite v0.1.0 [M+H]+ 170.49593 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.6315183 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.58908 predictedDeepCCS 1.0 (2019)
Targets
Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:53