Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
Identification
NameOxybenzone
Accession NumberDB01428
Typesmall molecule
Groupsapproved
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
SynonymLanguageCode
(2-Hydroxy-4-methoxyphenyl)phenylmethanoneNot AvailableNot Available
2-Benzoyl-5-methoxyphenolNot AvailableNot Available
2-Hydroxy-4-methoxybenzophenoneNot AvailableNot Available
4-Methoxy-2-hydroxybenzophenoneNot AvailableNot Available
4-Methoxy-2-hydroxybenzophenone butyric acidNot AvailableNot Available
OxibenzonaSpanishINN
OxybenzonumLatinINN
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number131-57-7
WeightAverage: 228.2433
Monoisotopic: 228.07864425
Chemical FormulaC14H12O3
InChI KeyInChIKey=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
Mass Specshow(8.57 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzophenones
Direct parentBenzophenones
Alternative parentsDiphenylmethanes; Salicylic Acid and Derivatives; Methoxyphenols and Derivatives; Acetophenones; Benzoyl Derivatives; Anisoles; Alkyl Aryl Ethers; Ketones; Enols; Polyamines; Enolates
Substituentssalicylic acid or derivative; methoxyphenol; acetophenone; phenol ether; anisole; benzoyl; phenol derivative; alkyl aryl ether; ketone; enolate; ether; polyamine; enol; carbonyl group
Classification descriptionThis compound belongs to the benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
Pharmacology
IndicationUsed as an ingredient in sunscreen and other cosmetics.
PharmacodynamicsOxybenzone is an organic compound used in sunscreens. It is a derivative of benzophenone.
Mechanism of actionOxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationIn vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9973
Blood Brain Barrier + 0.8691
Caco-2 permeable + 0.9258
P-glycoprotein substrate Non-substrate 0.6198
P-glycoprotein inhibitor I Non-inhibitor 0.7188
P-glycoprotein inhibitor II Non-inhibitor 0.8124
Renal organic cation transporter Non-inhibitor 0.8178
CYP450 2C9 substrate Non-substrate 0.703
CYP450 2D6 substrate Non-substrate 0.8915
CYP450 3A4 substrate Non-substrate 0.6542
CYP450 1A2 substrate Inhibitor 0.911
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9437
CYP450 2C19 substrate Inhibitor 0.8995
CYP450 3A4 substrate Non-inhibitor 0.9258
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5
Ames test Non AMES toxic 0.9098
Carcinogenicity Non-carcinogens 0.8403
Biodegradation Not ready biodegradable 0.6452
Rat acute toxicity 1.6986 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9358
hERG inhibition (predictor II) Non-inhibitor 0.9337
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
LotionTopical
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point65.5 °CPhysProp
boiling point155 °C at 5.00E+00 mm HgPhysProp
logP3.79CHEM INSPECT TEST INST (1992)
Predicted Properties
PropertyValueSource
water solubility1.28e-01 g/lALOGPS
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 area46.53ChemAxon
rotatable bond count3ChemAxon
refractivity65.08ChemAxon
polarizability23.96ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  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
External Links
ResourceLink
KEGG DrugD05309
KEGG CompoundC14285
PubChem Compound4632
PubChem Substance46508419
ChemSpider4471
BindingDB50253134
PharmGKBPA164742933
WikipediaOxybenzone
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.7 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
Drug created on July 24, 2007 06:56 / Updated on September 16, 2013 17:14