Identification

Name
Dioxybenzone
Accession Number
DB11221
Type
Small Molecule
Groups
Approved
Description

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].

Structure
Thumb
Synonyms
  • 2,2'-Dihydroxy-4-methoxybenzophenone
External IDs
NSC-56769
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Viquin Forte With Moisturizing Aha - CrmDioxybenzone (3 %) + Hydroquinone (4 %) + Oxybenzone (2 %) + Padimate O (8 %)CreamTopicalIcn Pharmaceuticals1997-02-18Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Hydroquinone with sunscreensDioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) + Padimate O (80 mg/1g)CreamTopicalPreferreed Pharmaceuticals Inc.2012-01-302017-01-31Us
Nuquin HpDioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Padimate O (50 mg/1g)GelTopicalStratus Pharmaceuticals1999-09-142015-04-15Us
Nuquin HpDioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) + Padimate O (80 mg/1g)CreamTopicalStratus Pharmaceuticals2003-12-092015-04-09Us
Perrigo Hydroquinone with sunscreensDioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) + Padimate O (80 mg/1g)CreamTopicalPerrigo New York Inc.2008-10-232013-04-01Us
Perrigo Hydroquinone with sunscreensDioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Padimate O (50 mg/1g)GelTopicalPerrigo New York Inc.2009-02-042013-01-01Us
Categories
UNII
B762XZ551X
CAS number
131-53-3
Weight
Average: 244.246
Monoisotopic: 244.073558866
Chemical Formula
C14H12O4
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

Pharmacology

Indication

Indicated for use as an active sunscreen agent.

Associated Conditions
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].

TargetActionsOrganism
USex hormone-binding globulin
binder
Human
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.

Toxicity

No toxicokinetic data available.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:28959646]
  2. 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. [PubMed:23749905]
  3. 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. [PubMed:27690075]
  4. Pharmacokinetic and Toxicological Characterization of Repellent DEET and Sunscreen Oxybenzone (2011) - by DJ Fediuk [Link]
  5. BENZOPHENONE - National Library of Medicine HSDB Database - Toxnet - NIH [Link]
External Links
KEGG Drug
D03853
KEGG Compound
C14283
ChemSpider
8251
ChEBI
34208
ChEMBL
CHEMBL1326877
Wikipedia
Dioxybenzone
MSDS
Download (77.1 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelTopical
CreamTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)74MSDS
boiling point (°C)172.5MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.148 mg/mLALOGPS
logP3.15ALOGPS
logP3.97ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.78ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity67.06 m3·mol-1ChemAxon
Polarizability24.81 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
GC-MS Spectrum - EI-BGC-MSsplash10-00di-4940000000-2c3d6cfb7d965e13c292
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/MSsplash10-006x-6950000000-609717a3d05749da24af
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-006x-8900000000-41e6f76cb518b9945a46
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-052f-9500000000-dc8e101c89f7f7c5d22a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dj-0950000000-df004f08d4b1ec58c60c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-47c83a7c750591adc5ae
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01bc-9400000000-ed92fd233e08bf95537b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fk9-3900000000-89cfb6ab7edb964da658

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
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
Benzophenone / Diphenylmethane / Aryl-phenylketone / Methoxyphenol / Anisole / Phenoxy compound / Methoxybenzene / Benzoyl / Aryl ketone / Phenol ether
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzophenones (CHEBI:34208)

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:25349334]

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
  1. 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. [PubMed:24266910]

Drug created on December 03, 2015 09:51 / Updated on November 02, 2018 07:08