Avobenzone

Identification

Summary

Avobenzone is a sunscreen agent found in sunscreens that absorbs UV rays.

Brand Names
Meijer, Sumadan Wash
Generic Name
Avobenzone
DrugBank Accession Number
DB09495
Background

Avobenzone is dibenzoyl methane derivative. It is oil soluble ingredient. Avobenzone has the ability to absorb ultraviolet light over wider range of wavelengths. It is included in many commercially available sunscreens which are used as wide spectrum sunscreens. Avobenzone is very sensitive to light, to increase its stability and duration of action, photostablizers are added in the sunscreen product. Avobenzone has an absorption maximum of 357 nm. Sunscreens containing avobenzone is indicated for providing protection from the sun. In addition to limiting the skin's exposure to the sun, using sunscreen agents may help reduce long-term sun damage such as premature aging of the skin and skin cancer.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 310.393
Monoisotopic: 310.156894568
Chemical Formula
C20H22O3
Synonyms
  • Avobenzone
  • Butyl Methoxydibenzoylmethane
  • Parsol 1789

Pharmacology

Indication

Sun protection factor, added in the sunscreen products for its wide spectrum ultraviolet absorption properties.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for prophylaxis ofSunburn••• •••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

It blocks UVA I, UVA II, and UVB wavelengths, thereby limiting the impact of UV rays on skin. Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

A minimum toxic dose has not been established. Significant toxicity is not expected

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dynamic Skin Recovery SPF 50Lotion30 mg/1mLTopicalDermalogica2014-03-17Not applicableUS flag
Leaders Sunbuddy All Over SunSpray0.64 g/90mLTopicalLeaders Cosmetics Co.,ltd.2017-07-01Not applicableUS flag
Naked Sundays Golden Glow Body Sunscreen SPF50 100mlCream3 g/100mLTopicalWILD CHILD W A PTY LTD2022-06-01Not applicableUS flag
Ponds Clarant B3Cream100 g/3gTopicalTeresa Cecena Dba Genesis2015-05-26Not applicableUS flag
PONDS clarant b3Cream12 g/400gTopicalAll Natural Dynamics2012-06-29Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
(Re)Setting Refreshing Mist SPF 40Avobenzone (2.9 g/100mL) + Homosalate (9.8 g/100mL) + Octisalate (4.9 g/100mL) + Octocrylene (9.5 g/100mL)SprayTopicalSupergoop, LLC2022-01-05Not applicableUS flag
100 SPF CreamAvobenzone (3 % w/w) + Homosalate (15 % w/w) + Octisalate (5 % w/w) + Octocrylene (10 % w/w) + Oxybenzone (6 % w/w)CreamTopicalVital Science A Div. Of/Une Div. De Valeant Canada Ltd/Ltee2010-06-032014-08-27Canada flag
1000 Roses Daily Shade Facial SPF 18Avobenzone (25 mg/1mL) + Octisalate (50 mg/1mL) + Octocrylene (50 mg/1mL)LotionTopicalAndalou Naturals2014-03-01Not applicableUS flag
14-day Skin Rescue SPF 30Avobenzone (3 % w/w) + Homosalate (4 % w/w) + Octisalate (5 % w/w) + Octocrylene (2.35 % w/w) + Oxybenzone (6 % w/w)CreamTopicalJohnson & Johnson2009-02-162013-07-31Canada flag
15 Continuous Spray Sunscreen With Instant BronzerAvobenzone (2 %) + Octisalate (5 %) + Octocrylene (1.85 %)SprayTopicalPrime Enterprises, Inc.2018-04-092020-03-01Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4362 First Aid KitAvobenzone (1 g/100mL) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Homosalate (5 g/100mL) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Octinoxate (7.5 g/100mL) + Octisalate (5 g/100mL) + Oxybenzone (6 g/100mL) + Polymyxin B sulfate (5000 [iU]/1g) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)KitOphthalmic; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc.2018-09-13Not applicableUS flag
BEYOND THE SHAVE For MenAvobenzone (3.0 g/100mL) + Allantoin (0.5 g/100mL) + Dimethicone (2.9 g/100mL) + Homosalate (2.5 g/100mL) + Octasulfur (3.0 g/100mL) + Octisalate (5 g/100mL) + Octocrylene (2.7 g/100mL)KitTopicalRodan & Fields2017-06-01Not applicableUS flag
Conju Princess UV Sun BlockAvobenzone (0.03 mL/1mL) + Enzacamene (0.05 mL/1mL) + Octinoxate (0.075 mL/1mL) + Titanium dioxide (0.0249 mL/1mL) + Zinc oxide (0.01 mL/1mL)CreamTopicalConju Inc2010-12-18Not applicableUS flag
Conju Princess UV Sun BlockAvobenzone (0.03 mL/1mL) + Enzacamene (0.05 mL/1mL) + Octinoxate (0.075 mL/1mL) + Titanium dioxide (0.0249 mL/1mL) + Zinc oxide (0.01 mL/1mL)CreamTopicalConju Inc2010-12-18Not applicableUS flag
CoreTex Professional Outdoor Skin Protection WalletAvobenzone (1 g/100mL) + Avobenzone (1 g/100g) + Avobenzone (3 g/100mL) + Benzocaine (6 g/100mL) + Diphenhydramine hydrochloride (2 g/100mL) + Ethanol (62.5 mL/100mL) + Homosalate (5 g/100mL) + Homosalate (5 g/100g) + Homosalate (7.5 g/100mL) + Octinoxate (7.5 g/100mL) + Octinoxate (7.5 g/100g) + Octisalate (5 g/100mL) + Octisalate (5 g/100g) + Octisalate (5 g/100mL) + Octocrylene (2.5 g/100mL) + Oxybenzone (6 g/100mL) + Oxybenzone (6 g/100g) + Oxybenzone (6 g/100mL) + Synthetic camphor (0.1 g/100mL) + Zinc acetate dihydrate (1 g/100mL)Gel; Kit; Lipstick; Liquid; Lotion; SwabTopicalCoreTex Products Inc2019-11-27Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Linear 1,3-diarylpropanoids
Sub Class
Chalcones and dihydrochalcones
Direct Parent
Retro-dihydrochalcones
Alternative Parents
Alkyl-phenylketones / Butyrophenones / Phenylpropanes / Phenoxy compounds / Methoxybenzenes / Benzoyl derivatives / Aryl alkyl ketones / Anisoles / Beta-diketones / Alkyl aryl ethers
show 2 more
Substituents
1,3-dicarbonyl compound / 1,3-diketone / Alkyl aryl ether / Alkyl-phenylketone / Anisole / Aromatic homomonocyclic compound / Aryl alkyl ketone / Aryl ketone / Benzenoid / Benzoyl
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
G63QQF2NOX
CAS number
70356-09-1
InChI Key
XNEFYCZVKIDDMS-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione
SMILES
COC1=CC=C(C=C1)C(=O)CC(=O)C1=CC=C(C=C1)C(C)(C)C

References

General References
  1. MSDS [Link]
  2. article [Link]
  3. product info [Link]
PubChem Compound
51040
PubChem Substance
310265226
ChemSpider
46261
RxNav
45045
ChEBI
134751
ChEMBL
CHEMBL1200522
ZINC
ZINC000000000973
Wikipedia
Avobenzone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionCoronavirus Disease 2019 (COVID‑19) / Sports Nutrition1
4CompletedSupportive CareAtrophic Vaginitis / Endometrial Hyperplasia / Pelvic Organ Prolapse (POP)1
4CompletedSupportive CareSkin Irritation1
4CompletedTreatmentAcne Prone Skin1
4CompletedTreatmentActinic Keratosis (AK)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOphthalmic; Respiratory (inhalation); Topical
OintmentTopical
GelCutaneous
SalveTopical
LiquidNot applicable1 kg/1kg
PatchTopical
Cream, augmentedTopical
SprayCutaneous
Cream; kit; oil; stickTopical
KitOral; Topical
CreamTopical
JellyTopical
PowderTopical
GelTopical
AerosolTopical
ClothTopical
Gel; kit; lotionTopical
Gel; kit; lipstick; liquid; lotion; swabTopical
Cream; gel; kit; lotionTopical
LotionTopical30 mg/1mL
Kit; stickTopical
Cream; kitTopical
SpongeTopical
OilTopical
Kit; lipstickTopical
SprayTopical0.64 g/90mL
LipstickTopical
LiquidTopical
CreamTopical3 g/100mL
Cream; kit; lotionTopical
EmulsionTopical
Kit; lotionTopical
SuspensionTopical
CreamTopical100 g/3g
CreamTopical12 g/400g
CreamTopical3 g/100g
Jelly; kitTopical
LotionCutaneous
StickTopical
SprayOral
KitTopical
PasteTopical
SoapTopical
SprayTopical
Liquid; sprayTopical
LotionOral
Kit; liquidTopical
LotionTopical
Gel; kitTopical
SolutionTopical
Aerosol, foamTopical
Aerosol, sprayTopical
CreamCutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000622 mg/mLALOGPS
logP4.98ALOGPS
logP4.56Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)9.88Chemaxon
pKa (Strongest Basic)-4.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area43.37 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity91.75 m3·mol-1Chemaxon
Polarizability34.86 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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-004i-0301009001-6899df9cdc4f6074943c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1619000000-f818edacf6d19a9f7160
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03dr-3900000000-0c3f2cd90f17bc9fa504
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0903000000-55b50daa82e16db1193f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0309000000-7136da4c4eedd3000c52
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-2900000000-f488b372fff43bfff092
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a7i-2945000000-c496a5c007eb16639f06
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-f46e86e8f2227df6d703
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-5930000000-8349d8193b0078d0330b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-202.5385433
predicted
DarkChem Lite v0.1.0
[M-H]-181.2086
predicted
DeepCCS 1.0 (2019)
[M+H]+203.7680433
predicted
DarkChem Lite v0.1.0
[M+H]+183.74634
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.90752
predicted
DeepCCS 1.0 (2019)

Drug created at November 30, 2015 19:10 / Updated at February 21, 2021 18:52