U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H22O3
Molecular Weight 310.3869
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AVOBENZONE

SMILES

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

InChI

InChIKey=XNEFYCZVKIDDMS-UHFFFAOYSA-N
InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.wikidoc.org/index.php/Avobenzone | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=de3fd7fb-4a28-4db8-9a4d-d7fdd2e45daf

Avobenzone is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays. It helps prevent sunburn. Avobenzone works by absorbing the rays and converting them to energy that is less damaging to the skin.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
SHADE UVAGUARD

Approved Use

helps prevent sunburn; higher SPF gives more sunburn protection; helps provide protection from UVA rays (short and long wavelengths).

Launch Date

7.2368639E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.5 ng/mL
0.81 g 4 times / day multiple, topical
dose: 0.81 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
AVOBENZONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.1 ng/mL
0.81 g 4 times / day steady-state, topical
dose: 0.81 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
AVOBENZONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
45.2 h
0.81 g 4 times / day steady-state, topical
dose: 0.81 g
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
AVOBENZONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3.7 g 1.3 times / day multiple, topical (median)
Recommended
Dose: 3.7 g, 1.3 times / day
Route: topical
Route: multiple
Dose: 3.7 g, 1.3 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 3.69 years (range: 0.64-48.15 years)
n = 79
Health Status: healthy
Age Group: 3.69 years (range: 0.64-48.15 years)
Sex: M+F
Population Size: 79
Sources:
Other AEs: Dermatitis, Eczema...
Other AEs:
Dermatitis (2.5%)
Eczema (1.3%)
Sources:
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Other AEs: Acne, Dermatitis...
Other AEs:
Acne (4.8%)
Dermatitis (2.8%)
Dry skin (1.2%)
Eczema (1.2%)
Erythema (1.2%)
Pruritus (2%)
Rosacea (0.4%)
Seborrhea (0.8%)
Skin discomfort (1.2%)
Sunburn (0.8%)
Conjunctivitis (0.8%)
Taste perversion (0.4%)
Sources:
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Other AEs: Dermatitis, Eczema...
Other AEs:
Dermatitis (2.8%)
Eczema (0.4%)
Erythema (0.8%)
Skin discomfort (0.8%)
Sunburn (1.6%)
Conjunctivitis (0.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Eczema 1.3%
3.7 g 1.3 times / day multiple, topical (median)
Recommended
Dose: 3.7 g, 1.3 times / day
Route: topical
Route: multiple
Dose: 3.7 g, 1.3 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 3.69 years (range: 0.64-48.15 years)
n = 79
Health Status: healthy
Age Group: 3.69 years (range: 0.64-48.15 years)
Sex: M+F
Population Size: 79
Sources:
Dermatitis 2.5%
3.7 g 1.3 times / day multiple, topical (median)
Recommended
Dose: 3.7 g, 1.3 times / day
Route: topical
Route: multiple
Dose: 3.7 g, 1.3 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 3.69 years (range: 0.64-48.15 years)
n = 79
Health Status: healthy
Age Group: 3.69 years (range: 0.64-48.15 years)
Sex: M+F
Population Size: 79
Sources:
Rosacea 0.4%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Taste perversion 0.4%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Conjunctivitis 0.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Seborrhea 0.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Sunburn 0.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Dry skin 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Eczema 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Erythema 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Skin discomfort 1.2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Pruritus 2%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Dermatitis 2.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Acne 4.8%
1.6 g 1.1 times / day multiple, topical (median)
Recommended
Dose: 1.6 g, 1.1 times / day
Route: topical
Route: multiple
Dose: 1.6 g, 1.1 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 35.44 years (range: 12.04-83.43 years)
n = 248
Health Status: healthy
Age Group: 35.44 years (range: 12.04-83.43 years)
Sex: M+F
Population Size: 248
Sources:
Conjunctivitis 0.4%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Eczema 0.4%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Erythema 0.8%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Skin discomfort 0.8%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Sunburn 1.6%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Dermatitis 2.8%
3.1 g 1.2 times / day multiple, topical (median)
Recommended
Dose: 3.1 g, 1.2 times / day
Route: topical
Route: multiple
Dose: 3.1 g, 1.2 times / day
Co-administed with::
ecamsule
octocrylene
titanium dioxide
Sources:
healthy, 6.69 years (range: 0.5-67.95 years)
n = 246
Health Status: healthy
Age Group: 6.69 years (range: 0.5-67.95 years)
Sex: M+F
Population Size: 246
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Multiple chemical sensitivities, including iatrogenic allergic contact dermatitis, in a patient with chronic actinic dermatitis: implications for management.
1996 Sep
The effects of derivatives of the nitroxide tempol on UVA-mediated in vitro lipid and protein oxidation.
2002 Jul 1
Protection against UVB irradiation by natural filters extracted from lichens.
2002 Nov
Lack of in vitro protection by a common sunscreen ingredient on UVA-induced cytotoxicity in keratinocytes.
2004 Oct 15
Evaluation of the photostability of different UV filter combinations in a sunscreen.
2006 Jan 13
Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation.
2006 Mar 1
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
A new sunscreen agent.
2007 May 21
Influence of hydroxypropyl-beta-cyclodextrin on transdermal penetration and photostability of avobenzone.
2008 Jun
Role of UV light in photodamage, skin aging, and skin cancer: importance of photoprotection.
2009
Evaluation of spray congealing as technique for the preparation of highly loaded solid lipid microparticles containing the sunscreen agent, avobenzone.
2009 Aug
Polymorphism and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone.
2010 Feb 24
Determination of organic UV filters in water by stir bar sorptive extraction and direct analysis in real-time mass spectrometry.
2010 May
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor.
2015 Mar 1
Patents

Sample Use Guides

apply liberally 15 min before sun exposure. reapply as needed or after towel drying, 40 min of swimming, or perspiring.
Route of Administration: Topical
In Vitro Use Guide
Sources: DOI: 10.7324/JAPS.2015.50611
Avobenzone 2% and ethyl ascorbic acid2% represented the best photostability with avobenzone concentrations decrease by 11,82% for 15 hour using UVA lamp irradiation 4,7 mW/cm2.
Name Type Language
AVOBENZONE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NEOHELIOPAN 357
Brand Name English
AVOBENZONE [USP-RS]
Common Name English
Avobenzone [WHO-DD]
Common Name English
NSC-758680
Code English
AVOBENZONE COMPONENT OF ANTHELIOS SX
Common Name English
AVOBENZONE COMPONENT OF SHADE UVAGUARD
Common Name English
1,3-PROPANEDIONE, 1-(4-(1,1-DIMETHYLETHYL)PHENYL)-3-(4-METHOXYPHENYL)-
Systematic Name English
ESCALOL 517
Brand Name English
4-METHOXY-4'-TERT-BUTYLDIBENZOYLMETHANE
Common Name English
BUTYL METHOXYDIBENZOYLMETHANE [INCI]
Common Name English
1-(4-TERT-BUTYLPHENYL)-3-(4-METHOXYPHENYL)PROPAN-1,3-DIONE
Systematic Name English
BUTYL METHOXYDIBENZOYLMETHANE
INCI  
INCI  
Official Name English
AVOBENZONE [MART.]
Common Name English
AVOBENZONE [USP IMPURITY]
Common Name English
AVOBENZONE [MI]
Common Name English
AVOBENZONE [HSDB]
Common Name English
CAPITAL SOLEIL COMPONENT AVOBENZONE
Common Name English
ANTHELIOS SX COMPONENT AVOBENZONE
Common Name English
avobenzone [INN]
Common Name English
EUSOLEX 9020
Brand Name English
AVOBENZONE [ORANGE BOOK]
Common Name English
AVOBENZONE [USP MONOGRAPH]
Common Name English
AVOBENZONE COMPONENT OF CAPITAL SOLEIL
Common Name English
AVOBENZONE [USAN]
Common Name English
PARSOL 1789
Brand Name English
SHADE UVAGUARD COMPONENT AVOBENZONE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 142401
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
NCI_THESAURUS C851
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
CFR 21 CFR 352.10
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
Code System Code Type Description
EVMPD
SUB05617MIG
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
RXCUI
45045
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY RxNorm
USAN
AA-89
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
WIKIPEDIA
AVOBENZONE
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
INN
6480
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
FDA UNII
G63QQF2NOX
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
PUBCHEM
51040
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200522
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
EPA CompTox
DTXSID9044829
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
HSDB
7423
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
DAILYMED
G63QQF2NOX
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
ECHA (EC/EINECS)
274-581-6
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
MERCK INDEX
m2151
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1045337
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
NCI_THESAURUS
C47406
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
NSC
758680
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
DRUG CENTRAL
4242
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
CAS
70356-09-1
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
DRUG BANK
DB09495
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY
SMS_ID
100000086882
Created by admin on Fri Dec 15 15:23:18 UTC 2023 , Edited by admin on Fri Dec 15 15:23:18 UTC 2023
PRIMARY