Identification
- Summary
Dioxybenzone is a benzophenone derivative used in sunscreens to block UVB and short-wave UVA radiation.
- Generic Name
- Dioxybenzone
- DrugBank Accession Number
- DB11221
- Background
Dioxybenzone, or benzophenone-8, is an organic compound derived from Benzophenone that is used as a sunscreen agent. It absorbed UV-B and UV-AII rays. Dioxybenzone is an approved sunscreen ingredient in concentrations up to 3% 4.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Dioxybenzone (DB11221)
- Weight
- Average: 244.246
Monoisotopic: 244.073558866 - Chemical Formula
- C14H12O4
- Synonyms
- 2,2'-Dihydroxy-4-methoxybenzophenone
- Dioxybenzone
- External IDs
- NSC-56769
Pharmacology
- Indication
Indicated for use as an active sunscreen agent.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for prophylaxis of Sunburn ••• ••• - 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
Dioxybenzone is a sunscreen agent and chemical UV filter that absorbs UV-B rays and UV-AII rays to limit their penetration into human skin. In a screening protocol consisting of the in vitro EBV-EA activation assay followed by the in vivo confirmation test in the two-stage mouse skin cancer model utilizing NOR-1 as inducer and TPA as promoter of tumour, dioxybenzone exhibited a significant chemopreventive activity against mouse skin carcinogenesis which correlated with their antioxidant potency 2. There is some evidence that suggests some benzophenones and their hydroxylated metabolites act as weak estrogens in the environment; however similar effect of dioxybenzone has not been established 5.
- Mechanism of action
Emitted by the sun, UVA-II rays, which range at 320–400 nm and are not absorbed by the ozone layer, and UVB rays, which range 290–320 nm and are partially absorbed by the ozone layer and exert a damaging effect on human skin, including basal cell carcinoma and melanoma 4. As a chemical filter, dioxybenzone absorb these rays to prevent their penetration into the skin and attenuate long-term skin damage caused by UV radiation from the sun. In a rat uterine cytosolic estrogen receptor (ER) competitive binding assay, dioxybenzone was not found to be a ER-binder 3.
Target Actions Organism USex hormone-binding globulin binderHumans - Absorption
Dioxybenzone is a derivative of benzophenone. In monkeys, percutaneous absorption of benzophenone was observed 4. Other derivatives of benzophenone are capable of crossing the skin via direct penetration through the intercellular laminae of the stratum corneum (SC) or by passive diffusion by high-concentration gradient into the systemic circulation, where they are transported to different tissues including liver and brain 1.
- Volume of distribution
No pharmacokinetic data available.
- Protein binding
No pharmacokinetic data available.
- Metabolism
No pharmacokinetic data available.
- Route of elimination
No pharmacokinetic data available.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
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No toxicokinetic data 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
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.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Viquin Forte With Moisturizing Aha - Crm Dioxybenzone (3 %) + Hydroquinone (4 %) + Oxybenzone (2 %) + Padimate O (8 %) Cream Topical Icn Pharmaceuticals 1997-02-18 2005-04-26 Canada 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Hydroquinone with sunscreens Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) + Padimate O (80 mg/1g) Cream Topical Preferreed Pharmaceuticals Inc. 2012-01-30 2017-01-31 US 
Nuquin Hp Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Padimate O (50 mg/1g) Gel Topical Stratus Pharmaceuticals 1999-09-14 2015-04-15 US Nuquin Hp Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) + Padimate O (80 mg/1g) Cream Topical Stratus Pharmaceuticals 2003-12-09 2015-04-09 US Perrigo Hydroquinone with sunscreens Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Padimate O (50 mg/1g) Gel Topical Perrigo New York Inc. 2009-02-04 2013-01-01 US Perrigo Hydroquinone with sunscreens Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) + Padimate O (80 mg/1g) Cream Topical Perrigo New York Inc. 2008-10-23 2013-04-01 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
- Diphenylmethanes / Aryl-phenylketones / Methoxyphenols / Phenoxy compounds / Methoxybenzenes / Benzoyl derivatives / Anisoles / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids show 3 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Aryl ketone / Aryl-phenylketone / Benzophenone / Benzoyl / Diphenylmethane show 12 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzophenones (CHEBI:34208)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- B762XZ551X
- CAS number
- 131-53-3
- InChI Key
- MEZZCSHVIGVWFI-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H12O4/c1-18-9-6-7-11(13(16)8-9)14(17)10-4-2-3-5-12(10)15/h2-8,15-16H,1H3
- IUPAC Name
- 2-(2-hydroxybenzoyl)-5-methoxyphenol
- SMILES
- COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1O
References
- General References
- Ruszkiewicz JA, Pinkas A, Ferrer B, Peres TV, Tsatsakis A, Aschner M: Neurotoxic effect of active ingredients in sunscreen products, a contemporary review. Toxicol Rep. 2017 May 27;4:245-259. doi: 10.1016/j.toxrep.2017.05.006. eCollection 2017. [Article]
- Rao GS, Tokuda H, Ichiishi E, Takasaki M, Iida A, Suzuki N, Konoshima T, Kapadia GJ: Oral chemoprevention of skin cancer in mice by benzophenone sunscreens dioxybenzone and octabenzone in drinking water. Anticancer Res. 2013 Jun;33(6):2535-40. [Article]
- Hong H, Rua D, Sakkiah S, Selvaraj C, Ge W, Tong W: Consensus Modeling for Prediction of Estrogenic Activity of Ingredients Commonly Used in Sunscreen Products. Int J Environ Res Public Health. 2016 Sep 29;13(10). pii: ijerph13100958. doi: 10.3390/ijerph13100958. [Article]
- Pharmacokinetic and Toxicological Characterization of Repellent DEET and Sunscreen Oxybenzone (2011) - by DJ Fediuk [Link]
- BENZOPHENONE - National Library of Medicine HSDB Database - Toxnet - NIH [Link]
- External Links
- KEGG Drug
- D03853
- KEGG Compound
- C14283
- ChemSpider
- 8251
- 23350
- ChEBI
- 34208
- ChEMBL
- CHEMBL1326877
- ZINC
- ZINC000000037293
- Wikipedia
- Dioxybenzone
- MSDS
- Download (77.1 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Gel Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 74 MSDS boiling point (°C) 172.5 MSDS - Predicted Properties
Property Value Source Water Solubility 0.148 mg/mL ALOGPS logP 3.15 ALOGPS logP 3.97 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 6.78 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.76 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 67.06 m3·mol-1 Chemaxon Polarizability 24.81 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]- 166.5409361 predictedDarkChem Lite v0.1.0 [M-H]- 166.8002361 predictedDarkChem Lite v0.1.0 [M-H]- 153.63228 predictedDeepCCS 1.0 (2019) [M+H]+ 166.9695361 predictedDarkChem Lite v0.1.0 [M+H]+ 167.3125361 predictedDarkChem Lite v0.1.0 [M+H]+ 155.99028 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.0996361 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.3789361 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.08344 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
Carriers
- Kind
- Protein
- Organism
- Rat
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds estrogens, fatty acids and metals.
- Specific Function
- Metal ion binding
- Gene Name
- Afp
- Uniprot ID
- P02773
- Uniprot Name
- Alpha-fetoprotein
- Molecular Weight
- 68385.48 Da
References
- Shen J, Zhang W, Fang H, Perkins R, Tong W, Hong H: Homology modeling, molecular docking, and molecular dynamics simulations elucidated alpha-fetoprotein binding modes. BMC Bioinformatics. 2013;14 Suppl 14:S6. doi: 10.1186/1471-2105-14-S14-S6. Epub 2013 Oct 9. [Article]
Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:53