OXYBENZONE

US Previously Marketed

First approved in 1966

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12O3
Molecular Weight	228.2433
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C(=O)C2=CC=CC=C2)C(O)=C1

InChI

InChIKey=DXGLGDHPHMLXJC-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.thedermreview.com/oxybenzone/

Oxybenzone is one of the more popular molecules used by chemists during the manufacturing of cosmetics and is included in sunscreen for UV protection. The chemical is often used to stabilize and strengthen the color and scent of skin care products, but its widest use is in the form of sun block. Unfortunately, the debate about the safety of oxybenzone is still ongoing. One of the biggest concerns in the medical community about the widespread use of the molecule comes from the fact that it’s easily absorbed into the body. This absorption raises concerns that oxybenzone may accumulate in the body, eventually leading to potentially toxic levels of the chemical, which can affect the endocrine system.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sunburns 22 Sources: http://www.hendricks.org/HealthLibrary/default.aspx?sid=1&pTitle=&ContentTypeID=26&ContentID=3437&pTitle=Drug&alpha=S&AdditionalTitle=Shade%20UVA%20Guard%C2%AE	Preventing		Approved 8583	SHADE UVAGUARD Approved Use To prevent sunburns. Launch Date 1992

C_max

Value	Dose	Co-administered	Analyte	Population
94.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
258.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² 4 times / day multiple, topical dose: 2 mg/cm² route of administration: Topical experiment type: MULTIPLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
85.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
180.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² 4 times / day multiple, topical dose: 2 mg/cm² route of administration: Topical experiment type: MULTIPLE co-administered:		OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1204 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3443.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² 4 times / day multiple, topical dose: 2 mg/cm² route of administration: Topical experiment type: MULTIPLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1159.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2757.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² 4 times / day multiple, topical dose: 2 mg/cm² route of administration: Topical experiment type: MULTIPLE co-administered:		OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
78.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
79.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31961417/	2 mg/cm² single, topical dose: 2 mg/cm² route of administration: Topical experiment type: SINGLE co-administered: AVOBENZONE	AVOBENZONE	OXYBENZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 % single, topical Accidental dose Dose: 10 % Route: topical Route: single Dose: 10 % Sources: https://pubmed.ncbi.nlm.nih.gov/1935041/	unknown Health Status: unknown Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1935041/	Other AEs: Eczema... Other AEs: Eczema Sources: https://pubmed.ncbi.nlm.nih.gov/1935041/
6 % 4 times / day multiple, topical Recommended Dose: 6 %, 4 times / day Route: topical Route: multiple Dose: 6 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31058986/	unknown Health Status: unknown Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31058986/	Other AEs: Rash... Other AEs: Rash (16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/31058986/

AEs

AE	Significance	Dose	Population
Eczema		10 % single, topical Accidental dose Dose: 10 % Route: topical Route: single Dose: 10 % Sources: https://pubmed.ncbi.nlm.nih.gov/1935041/	unknown Health Status: unknown Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1935041/
Rash	16.7%	6 % 4 times / day multiple, topical Recommended Dose: 6 %, 4 times / day Route: topical Route: multiple Dose: 6 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31058986/	unknown Health Status: unknown Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/31058986/

PubMed

Title	Date	PubMed
Quantification of organic eluates from polymerized resin-based dental restorative materials by use of GC/MS.	2007-05-01	17127109
Determination of UV filters and antimicrobial agents in environmental water samples.	2007-02	17136341
Expression of osteoblast marker genes in rat calvarial osteoblast-like cells, and effects of the endocrine disrupters diphenylolpropane, benzophenone-3, resveratrol and silymarin.	2006-12-15	17069779
Parabens as urinary biomarkers of exposure in humans.	2006-12	17185273
Endocrine disruptors and rat adrenocortical function: studies on freshly dispersed and cultured cells.	2006-12	17089022
A validated method for the determination of traces of UV filters in fish using LC-MS/MS.	2006-11	17072605
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Simultaneous determination of benzophenone-type UV filters in water and soil by gas chromatography-mass spectrometry.	2006-10-27	16890944
Sunscreen enhancement of UV-induced reactive oxygen species in the skin.	2006-10-15	17015167
Photopatch testing of 1155 patients: results of the U.K. multicentre photopatch study group.	2006-10	16965423
Estradiol and resveratrol stimulating effect on osteocalcin, but not osteonectin and collagen-1alpha gene expression in primary culture of rat calvarial osteoblast-like cells.	2006-10	16964405
Preparation and characterization of oxybenzone-loaded gelatin microspheres for enhancement of sunscreening efficacy.	2006-08-01	16877306
Causal agents of photoallergic contact dermatitis diagnosed in the national institute of dermatology of Colombia.	2006-08	16869867
Photoallergic contact cheilitis due to oxybenzone found in a lip cosmetic.	2006-07	16842557
Activity related to the carcinogenicity of plastic additives in the benzophenone group.	2006-06-01	16780223
Bioactive constituents from Chinese natural medicines. XVII. constituents with radical scavenging effect and new glucosyloxybenzyl 2-isobutylmalates from Gymnadenia conopsea.	2006-04	16595954
Estrogenic activities of chemicals related to food contact plastics and rubbers tested by the yeast two-hybrid assay.	2006-04	16546889
Comparison of in vitro and in vivo estrogenic activity of UV filters in fish.	2006-04	16403853
In vitro permeation of repellent DEET and sunscreen oxybenzone across three artificial membranes.	2006-03-09	16414221
Photocontact allergy to oxybenzone and contact allergy to lignocaine and prilocaine.	2006-03	16524446
Photoallergic contact dermatitis from ketoprofen in southern Sweden.	2006-03	16524438
Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation.	2006-02	16433806
Evaluation of the photostability of different UV filter combinations in a sunscreen.	2006-01-13	16289662
Influence of complexation with cyclodextrins on photo-induced free radical production by the common sunscreen agents octyl-dimethylaminobenzoate and octyl-methoxycinnamate.	2006-01	16454205
In vivo bioassay-guided fractionation of marine sediment extracts from the Southern California Bight, USA, for estrogenic activity.	2005-11	16398118
Separation via flotation, spectrophotometric speciation, and determination of vanadium(IV) in wastes of power stations.	2005-11	16317901
Additive estrogenic effects of mixtures of frequently used UV filters on pS2-gene transcription in MCF-7 cells.	2005-10-15	16183391
Quantification of urinary conjugates of bisphenol A, 2,5-dichlorophenol, and 2-hydroxy-4-methoxybenzophenone in humans by online solid phase extraction-high performance liquid chromatography-tandem mass spectrometry.	2005-10	16132150
Photoallergic and allergic reaction to 2-hydroxy-4-methoxybenzophenone (sunscreen) and allergy to cetyl alcohol in cosmetic cream.	2005-09	16128759
Screening for androgen receptor activities in 253 industrial chemicals by in vitro reporter gene assays using AR-EcoScreen cells.	2005-09	15950433
Fading of artificial hair color and its prevention by photofilters.	2005-08-09	16538296
Simultaneous analysis of insect repellent DEET, sunscreen oxybenzone and five relevant metabolites by reversed-phase HPLC with UV detection: application to an in vivo study in a piglet model.	2005-08-05	15993660
[Estrogenic activity of ultraviolet absorbers and the related compounds].	2005-08	16079615
Assay of common sunscreen agents in suncare products by high-performance liquid chromatography on a cyanopropyl-bonded silica column.	2005-06-15	15925215
The effect of packaging materials on the stability of sunscreen emulsions.	2005-06-13	15885937
In vitro evaluation of concurrent use of commercially available insect repellent and sunscreen preparations.	2005-06	15948991
Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens, and musks.	2005-02-27	15799449
Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss Lakes.	2005-02-15	15773466
Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays.	2005-02	15537743
Sunscreens - which and what for?	2004-12-13	16113595
Effects of estradiol, benzophenone-2 and benzophenone-3 on the expression pattern of the estrogen receptors (ER) alpha and beta, the estrogen receptor-related receptor 1 (ERR1) and the aryl hydrocarbon receptor (AhR) in adult ovariectomized rats.	2004-12-01	15458797
Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone.	2004-11-25	15560736
Sunscreen penetration of human skin and related keratinocyte toxicity after topical application.	2004-09-28	15908756
Recrystallization in different sunscreen formulations after cutaneous application.	2004-07	17134426
Systemic absorption of the sunscreens benzophenone-3, octyl-methoxycinnamate, and 3-(4-methyl-benzylidene) camphor after whole-body topical application and reproductive hormone levels in humans.	2004-07	15191542
[First derivative spetrophotometric direct determination of 2-hydroxy-4-methoxybenzo phenone in polyester resin by computer assistant].	2004-06	15766192
In-vitro permeation of the insect repellent N,N-diethyl-m-toluamide (DEET) and the sunscreen oxybenzone.	2004-05	15142339
Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes.	2004-05	15051365
Liquid chromatographic assay for common sunscreen agents: application to in vivo assessment of skin penetration and systemic absorption in human volunteers.	2004-04-25	15063329
Contact and photocontact allergy to ketoprofen. The Belgian experience.	2004-04	15186381

Patents

Sample Use Guides

In Vivo Use Guide

Apply evenly and liberally to all exposed areas of the skin 30 minutes before any sun exposure.

Route of Administration: Topical

In Vitro Use Guide

Unknown

Name

Type

Language

BENZOPHENONE-3

Preferred Name

English

OXYBENZONE

Official Name

English

ONGROSTAB HMB

Common Name

English

SHADE UVAGUARD COMPONENT OXYBENZONE

Common Name

English

OXYBENZONE [USP-RS]

Common Name

English

oxybenzone [INN]

Common Name

English

ADVASTAB 45

Common Name

English

VIOSORB 110

Common Name

English

Oxybenzone [WHO-DD]

Common Name

English

BENZOPHENONE-3 [VANDF]

Common Name

English

OXYBENZONE [MART.]

Common Name

English

OXYBENZONE [MI]

Common Name

English

OXYBENZONE [USP MONOGRAPH]

Common Name

English

OXYBENZONE [HSDB]

Common Name

English

NSC-7778

Code

English

OXYBENZONE [ORANGE BOOK]

Common Name

English

UVINUL 40

Brand Name

English

OXYBENZONE [USAN]

Common Name

English

2-Hydroxy-4-methoxybenzophenone

Systematic Name

English

TINOSORB B 3

Common Name

English

OXYBENZONE [VANDF]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 352.10