Sulisobenzone

Identification

Name
Sulisobenzone
Accession Number
DB11185
Type
Small Molecule
Groups
Approved
Description

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].

Structure
Thumb
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
External IDs
NSC-60584
Product Ingredients
IngredientUNIICASInChI Key
Benzophenone-5853Z42ZYAS6628-37-1KJCLYACXIWMFCC-UHFFFAOYSA-M
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Anti-frizz SheetsSwab2 g/100gTopicalNINGBO JIANGBEI OCEAN STAR TRADING CO.,LTD2015-09-15Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BENEFIT Triple Performing Facial Broad Spectrum SPF15Sulisobenzone (15 mg/1mL) + Avobenzone (30 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20 mg/1mL)CreamTopicalBenefit Cosmetics, LLC2015-08-22Not applicableUs
Benefit Triple Performing Facial Emulsion Broad Spectrum SPF 15Sulisobenzone (15 mg/1mL) + Avobenzone (30 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20 mg/1mL)EmulsionTopicalBenefit Cosmetics, LLC2011-07-28Not applicableUs
CD Hydra Life Pro-Youth Protective FluidSulisobenzone (15.0 mg/1mL) + Avobenzone (30.0 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20.0 mg/1mL)SolutionTopicalParfums Christian Dior2010-05-072015-03-25Us
CD Hydra Life Pro-Youth Protective SPF 15Sulisobenzone (10.0 mg/1mL) + Avobenzone (30.0 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octocrylene (20.0 mg/1mL)CreamTopicalParfums Christian Dior2010-05-072015-03-25Us
Face Oasis Plus Hydrating Fluid SPF 15Sulisobenzone (0.05 %) + Avobenzone (2.0 %) + Octisalate (5.0 %) + Oxybenzone (5.0 %)LotionTopicalH2 O Plus2009-08-172010-09-02Canada
Givenchy Radically No SurgeticsSulisobenzone (10.0 mg/1mL) + Avobenzone (10.0 mg/1mL) + Octinoxate (74.9 mg/1mL) + Octisalate (10.0 mg/1mL)CreamTopicalParfums Givenchy S.A.2010-07-262014-03-11Us
Guerlain Super Aqua-DaySulisobenzone (5 mg/1mL) + Octinoxate (74 mg/1mL) + Octocrylene (20 mg/1mL) + Oxybenzone (30 mg/1mL) + Titanium dioxide (24 mg/1mL)LiquidTopicalGuerlain S.A.2010-06-172014-04-09Us
Hawaiian Tropic Herbal Protective Gel 15 SPFSulisobenzone (0.1 %) + Ensulizole (4 %)GelTopicalTanning Research Laboratories, Inc.1997-05-022002-06-18Canada
Hawaiian Tropic Herbal Tanning Mist 2 SPFSulisobenzone (0.1 %) + Ensulizole (0.5 %)SprayTopicalTanning Research Laboratories, Inc.1997-05-022001-06-28Canada
Hydra Life CRème Pro-jeunesse Avec Protection Uva/uvbSulisobenzone (1.0 %) + Avobenzone (3.0 %) + Octinoxate (7.49 %) + Octocrylene (2.0 %)CreamTopicalParfums Christian Dior2011-12-22Not applicableCanada
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
Categories
UNII
1W6L629B4K
CAS number
4065-45-6
Weight
Average: 308.3
Monoisotopic: 308.03545928
Chemical Formula
C14H12O6S
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

Pharmacology

Indication

Sunscreening agents are used to prevent sunburn, actinic keratosis, and premature skin aging and to reduce the incidence of skin cancer [5].

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].

TargetActionsOrganism
ASkin epithelial cells
protector
Human
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
Toxicity

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].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:23815618]
  2. 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. [PubMed:26016852]
  3. Heurung AR, Raju SI, Warshaw EM: Benzophenones. Dermatitis. 2014 Jan-Feb;25(1):3-10. doi: 10.1097/DER.0000000000000025. [PubMed:24407064]
  4. Sulsibenzone [Link]
  5. SULISOBENZONE [Link]
  6. SULISOBENZONE [Link]
  7. Sulisobezone, U.S. Pharmacopoeia Monograph [Link]
  8. FDA - CFR - Code of Federal Regulations Title 21: PART 352 -- SUNSCREEN DRUG PRODUCTS FOR OVER-THE-COUNTER HUMAN USE [STAYED INDEFINITELY] [Link]
  9. ECHA Sulisobenzone toxicity study [Link]
  10. Sulisobenzone, Daily Med Search [Link]
  11. Benzophenone [Link]
  12. Benzophenone, science direct [Link]
  13. Derm Net NZ, Benzophenone [Link]
  14. Health Canada Monograph, Sunscreens [File]
  15. NTP Technical Report on the Toxicity Studies of Benzophenone [File]
External Links
PubChem Compound
19988
PubChem Substance
347827937
ChemSpider
18829
ChEBI
135312
ChEMBL
CHEMBL2059073
Wikipedia
Sulisobenzone
MSDS
Download (148 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SwabTopical2 g/100g
SolutionTopical
GelTopical
SprayTopical
CreamTopical
EmulsionTopical
LiquidTopical
LotionTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
PropertyValueSource
melting point (°C) 145MSDS
water solubility10 microgram/mLhttp://www.pharmacopeia.cn/v29240/usp29nf24s0_m80090.html
Predicted Properties
PropertyValueSource
Water Solubility0.214 mg/mLALOGPS
logP0.39ALOGPS
logP2.8ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.7 m3·mol-1ChemAxon
Polarizability29.14 Å3ChemAxon
Number of Rings2ChemAxon
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/MSsplash10-0a4i-0009000000-b7570e368c88fbc8d642
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0059000000-b9a35ff3e9d6a406e10d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03gi-7590000000-b7afd1d3d333b910051d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0009000000-c154c7f2b1e4927895e7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0009000000-c154c7f2b1e4927895e7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-06a746f7069331a7e1eb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-630b349ace208ebc90ac
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0039000000-2906928c028576eb0991
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0049000000-ad08ab192ca26f47f98f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a59-0397000000-664b396d8f30a365ead8

Taxonomy

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
Benzophenone / Diphenylmethane / Aryl-phenylketone / Benzenesulfonate / Methoxyphenol / Benzenesulfonyl group / Arylsulfonic acid or derivatives / 1-sulfo,2-unsubstituted aromatic compound / Anisole / Phenol ether
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

1. Skin epithelial cells
Kind
Group
Organism
Human
Pharmacological action
Yes
Actions
Protector
References
  1. Sulisobezone, U.S. Pharmacopoeia Monograph [Link]
  2. Sulsibenzone [Link]
  3. SULISOBENZONE [Link]

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 09:07