Identification

Name
Oxybenzone
Accession Number
DB01428
Type
Small Molecule
Groups
Approved
Description

Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone. It forms colorless crystals that are readily soluble in most organic solvents. It is used as an ingredient in sunscreen and other cosmetics because it absorbs UV-A ultraviolet rays.

Structure
Thumb
Synonyms
  • (2-Hydroxy-4-methoxyphenyl)phenylmethanone
  • 2-Benzoyl-5-methoxyphenol
  • 2-Hydroxy-4-methoxybenzophenone
  • 4-Methoxy-2-hydroxybenzophenone
  • 4-Methoxy-2-hydroxybenzophenone butyric acid
  • Benzophenone-3
  • Oxibenzona
  • Oxybenzonum
External IDs
NSC-7778
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Zep Sun Screen TowelsLiquid.05 g/100gTopicalZep, Inc2013-05-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
100 SPF CreamOxybenzone (6 %) + Avobenzone (3 %) + Homosalate (15 %) + Octisalate (5 %) + Octocrylene (10 %)CreamTopicalVital Science A Div. Of/Une Div. De Valeant Canada Ltd/Ltee2010-06-032014-08-27Canada
14-day Skin Rescue SPF 30Oxybenzone (6 %) + Avobenzone (3 %) + Homosalate (4 %) + Octisalate (5 %) + Octocrylene (2.35 %)CreamTopicalJohnson & Johnson2009-02-162013-07-31Canada
15 SPF Fps Premium SunscreenOxybenzone (2.0 %) + Avobenzone (3.0 %) + Ensulizole (2.0 %) + Octocrylene (10.0 %)LotionTopicalEmpack Spraytech Inc.2005-05-04Not applicableCanada
15 SPF Fps Sunscreen Lotion écran SolaireOxybenzone (3.0 %) + Avobenzone (0.9 %) + Octocrylene (3.0 %)LotionTopicalEnergizer Canada Inc2007-03-012011-07-29Canada
15 SPF Sunscreen Uva/uvb Protection Oil-free Milky SprayOxybenzone (2.0 %) + Avobenzone (3.0 %) + Octinoxate (5.0 %) + Octisalate (3.0 %) + Octocrylene (2.0 %)EmulsionTopicalCoty Canada Inc.2009-02-232013-07-24Canada
15 SPF Sunscreen Uva/uvb Protection Vitalizing Age-defying CreamOxybenzone (3.0 %) + Avobenzone (3.0 %) + Octinoxate (7.5 %) + Octisalate (5.0 %) + Octocrylene (2.0 %)CreamTopicalCoty Canada Inc.2009-02-232013-07-24Canada
24K Bio-Brightening Skin Tone Moisturizer SPF 30Oxybenzone (3.1 g/100g) + Avobenzone (1.5 g/100g) + Homosalate (6.2 g/100g) + Octinoxate (7.4 g/100g) + Octisalate (5 g/100g)CreamTopicalVivo Per Lei, Inc.2014-10-03Not applicableUs
29 by LYDIA MONDAVI Napa Valley BROAD SPECTRUM SPF 30 D VINE DAYOxybenzone (25 mg/mL) + Avobenzone (30 mg/mL) + Homosalate (100 mg/mL) + Octisalate (50 mg/mL) + Octocrylene (20 mg/mL)CreamTopical29 Luxury Goods, Inc.2013-10-16Not applicableUs
2X Sunblock SPF 50Oxybenzone (6 mL/100mL) + Avobenzone (3 mL/100mL) + Homosalate (15 mL/100mL) + Octocrylene (6 mL/100mL)LiquidTopicalNupur Formulations Inc2011-04-22Not applicableUs
30 Plus Sunblock SprayOxybenzone (4 %) + Homosalate (5 %) + Octinoxate (7.5 %) + Octisalate (5 %)Lotion; SprayTopicalTanning Research Laboratories, Inc.2000-02-282001-06-28Canada
Categories
UNII
95OOS7VE0Y
CAS number
131-57-7
Weight
Average: 228.2433
Monoisotopic: 228.07864425
Chemical Formula
C14H12O3
InChI Key
DXGLGDHPHMLXJC-UHFFFAOYSA-N
InChI
InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3
IUPAC Name
2-benzoyl-5-methoxyphenol
SMILES
COC1=CC(O)=C(C=C1)C(=O)C1=CC=CC=C1

Pharmacology

Indication

Used as an ingredient in sunscreen and other cosmetics.

Structured Indications
Pharmacodynamics

Oxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone.

Mechanism of action

Oxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.

TargetActionsOrganism
UProgesterone receptor
antagonist
Human
UAndrogen receptor
antagonist
Human
UEstrogen receptor alphaNot AvailableHuman
UEstrogen receptor betaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

In vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. Gonzalez H, Farbrot A, Larko O, Wennberg AM: Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation. Br J Dermatol. 2006 Feb;154(2):337-40. [PubMed:16433806 ]
External Links
Human Metabolome Database
HMDB15497
KEGG Drug
D05309
KEGG Compound
C14285
PubChem Compound
4632
PubChem Substance
46508419
ChemSpider
4471
BindingDB
50253134
ChEBI
34283
ChEMBL
CHEMBL1625
PharmGKB
PA164742933
Wikipedia
Oxybenzone
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (73.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingSupportive CareDermatologic Complications / Neoplasms, Malignant1
3CompletedSupportive CareDermatologic Complications / Unspecified Adult Solid Tumor, Protocol Specific1
4CompletedTreatmentHypertrophic Cicatrix / Hypertrophic Scars / Keloid Scars1
4CompletedTreatmentMelasma1
4TerminatedNot AvailableSkin Aging1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
SalveTopical
PasteTopical
Cloth; creamTopical
LiquidTopical
SprayTopical
GelTopical
StickOral
Gel; kit; lotionTopical
OilTopical
EmulsionTopical
Liquid; lotionTopical
Kit
JellyTopical
Cream, augmentedTopical
Lotion / shampooTopical
SolutionTopical
Aerosol, foamTopical
SuspensionTopical
Aerosol, sprayTopical
KitTopical
LotionCutaneous
ClothTopical
AerosolTopical
CreamTopical
OintmentTopical
Spray, suspensionTopical
StickTopical
SprayOral
Liquid; sprayTopical
Lotion; sprayTopical
LipstickTopical
LotionTopical
PowderTopical
LiquidTopical.05 g/100g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)65.5 °CPhysProp
boiling point (°C)155 °C at 5.00E+00 mm HgPhysProp
logP3.79CHEM INSPECT TEST INST (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.128 mg/mLALOGPS
logP3.35ALOGPS
logP3.62ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.07ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity65.08 m3·mol-1ChemAxon
Polarizability23.96 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9973
Blood Brain Barrier+0.8691
Caco-2 permeable+0.9258
P-glycoprotein substrateNon-substrate0.6198
P-glycoprotein inhibitor INon-inhibitor0.7188
P-glycoprotein inhibitor IINon-inhibitor0.8124
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.703
CYP450 2D6 substrateNon-substrate0.8915
CYP450 3A4 substrateNon-substrate0.6542
CYP450 1A2 substrateInhibitor0.911
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9437
CYP450 2C19 inhibitorInhibitor0.8995
CYP450 3A4 inhibitorNon-inhibitor0.9258
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.9098
CarcinogenicityNon-carcinogens0.8403
BiodegradationNot ready biodegradable0.6452
Rat acute toxicity1.6986 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9358
hERG inhibition (predictor II)Non-inhibitor0.9337
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Download (8.57 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-004i-0390000000-d20281152dd02868f0f4
GC-MS Spectrum - EI-BGC-MSsplash10-004i-1190000000-c313f66363430324ce8e
Mass Spectrum (Electron Ionization)MSsplash10-0fb9-5970000000-201ffa188f10c8981e9e
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-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-25520d89872ff52a3ed3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-91e535fa71de15e79004
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0390000000-440768455ae7530c1909
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0910000000-d7fdecc4ef3f7a731749
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-e961d0acc366c6018be1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-1900000000-7c8fdbbdfd111f438a02
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfs-5900000000-daad8bf207afcb7e0b35
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0090000000-f005541a3bcdeecd4a50
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0390000000-4d6d607f4d00d653af57
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0910000000-5bd3907cf283f3acd696
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-2952f2aadcf45f405c21
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-1900000000-d9d09a5a4ce6a4afa1f2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0zfs-5900000000-bd6b959b532a530b3906
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0udi-0900000000-c3d717596cccd924dc19
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0590000000-4e2b5ecc7de18b351252
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0900000000-465387cfd8d500df1516
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004j-9400000000-e9226c86961ff5d9d15b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ufr-0940000000-2a55f01ddfa3b0ff8f42
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ufr-0950000000-1544559b42fcf578bf82
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of chemical entities known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Benzenoids
Sub Class
Benzene and substituted derivatives
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
monomethoxybenzene, hydroxybenzophenone (CHEBI:34283 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005 Feb;83(2):264-72. Epub 2004 Nov 10. [PubMed:15537743 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005 Feb;83(2):264-72. Epub 2004 Nov 10. [PubMed:15537743 ]
  2. Araki N, Ohno K, Nakai M, Takeyoshi M, Iida M: Screening for androgen receptor activities in 253 industrial chemicals by in vitro reporter gene assays using AR-EcoScreen cells. Toxicol In Vitro. 2005 Sep;19(6):831-42. [PubMed:15950433 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [PubMed:16079615 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [PubMed:16079615 ]

Drug created on July 24, 2007 06:56 / Updated on October 02, 2017 04:58