Avobenzone

Identification

Name
Avobenzone
Accession Number
DB09495
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
Synonyms
  • Butyl Methoxydibenzoylmethane
  • Parsol 1789
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Balancing Dynamics Kit JafraKitJafra Cosmetics2012-11-16Not applicableUs
Dynamic Skin Recovery SPF 50Lotion30 mg/mLTopicalDermalogica2014-03-17Not applicableUs
Leaders Sunbuddy All Over SunSpray.64 g/90mLTopicalLeaders Cosmetics Co.,ltd.2017-07-01Not applicableUs
Octisalate, Avobenzone, Homosalate, Octocrylene SPF30KitTopicalJulep Nail Parlor2013-09-10Not applicableUs
Ponds Clarant B3Cream3 g/100gTopicalAll Natural Dynamics2012-06-29Not applicableUs
Ponds Clarant B3Cream100 g/3gTopicalTeresa Cecena Dba Genesis2015-05-26Not applicableUs
Ponds Vao-B3Cream3 g/100gTopicalAll Natural Dynamics2013-09-02Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
100 SPF CreamAvobenzone (3 %) + Homosalate (15 %) + Octisalate (5 %) + Octocrylene (10 %) + Oxybenzone (6 %)CreamTopicalVital Science A Div. Of/Une Div. De Valeant Canada Ltd/Ltee2010-06-032014-08-27Canada
1000 Roses Daily Shade Facial SPF 18Avobenzone (25 mg/mL) + Octisalate (50 mg/mL) + Octocrylene (50 mg/mL)LotionTopicalAndalou Naturals2014-03-01Not applicableUs
14-day Skin Rescue SPF 30Avobenzone (3 %) + Homosalate (4 %) + Octisalate (5 %) + Octocrylene (2.35 %) + Oxybenzone (6 %)CreamTopicalJohnson & Johnson2009-02-162013-07-31Canada
15 Continuous Spray Sunscreen With Instant BronzerAvobenzone (2 %) + Octisalate (5 %) + Octocrylene (1.85 %)SprayTopicalPrime Enterprises, Inc.2018-04-09Not applicableCanada
15 SPF Fps Premium SunscreenAvobenzone (3.0 %) + Ensulizole (2.0 %) + Octocrylene (10.0 %) + Oxybenzone (2.0 %)LotionTopicalEmpack Spraytech Inc.2005-05-04Not applicableCanada
15 SPF Fps Sunscreen Lotion écran SolaireAvobenzone (0.9 %) + Octocrylene (3.0 %) + Oxybenzone (3.0 %)LotionTopicalEnergizer Canada Inc2007-03-012011-07-29Canada
15 SPF Sunscreen Uva/uvb Protection Oil-free Milky SprayAvobenzone (3.0 %) + Octinoxate (5.0 %) + Octisalate (3.0 %) + Octocrylene (2.0 %) + Oxybenzone (2.0 %)EmulsionTopicalCoty Canada Inc.2009-02-232013-07-24Canada
15 SPF Sunscreen Uva/uvb Protection Vitalizing Age-defying CreamAvobenzone (3.0 %) + Octinoxate (7.5 %) + Octisalate (5.0 %) + Octocrylene (2.0 %) + Oxybenzone (3.0 %)CreamTopicalCoty Canada Inc.2009-02-232013-07-24Canada
15 Spray Gel Sunscreen With Instant BronzerAvobenzone (2 %) + Octisalate (5 %) + Octocrylene (1.85 %) + Oxybenzone (0.5 %)GelTopicalPrime Enterprises, Inc.2018-04-09Not applicableCanada
15 Tanning CVSAvobenzone (2 g/100mL) + Homosalate (10 g/100mL) + Octisalate (5 g/100mL) + Octocrylene (5 g/100mL)LotionTopicalProduct Quest Mff, Llc2014-11-062016-04-05Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
BEYOND THE SHAVE For MenAvobenzone + Allantoin + Dimethicone + Homosalate + Octisalate + Octocrylene + SulfurKitTopicalRodan & Fields2017-06-01Not applicableUs
Conju Princess UV Sun BlockAvobenzone (.03 mL/mL) + Enzacamene (.05 mL/mL) + Octinoxate (.075 mL/mL) + Titanium dioxide (.0249 mL/mL) + Zinc oxide (.01 mL/mL)CreamTopicalConju Inc2010-12-18Not applicableUs
Conju Princess UV Sun BlockAvobenzone (.03 mL/mL) + Enzacamene (.05 mL/mL) + Octinoxate (.075 mL/mL) + Titanium dioxide (.0249 mL/mL) + Zinc oxide (.01 mL/mL)CreamTopicalConju Inc2010-12-18Not applicableUs
Glytone Clarifying SunVanish with SunscreenAvobenzone (20 mg/g) + Hydroquinone (40 mg/g) + Octinoxate (75 mg/g) + Octocrylene (18.6 mg/g) + Oxybenzone (50 mg/g)CreamTopicalGenesis2012-06-13Not applicableUs
Laser Block 100 sunblockAvobenzone (.005 mL/mL) + Amiloxate (.02 mL/mL) + Enzacamene (.03 mL/mL) + Octinoxate (.07 mL/mL) + Titanium dioxide (.02 mL/mL) + Zinc oxide (.05 mL/mL)CreamTopicalUniversal Cosmetic Co., Ltd2010-08-04Not applicableUs
MediSpa Sunblock sunblockAvobenzone (.005 mL/mL) + Enzacamene (.03 mL/mL) + Octinoxate (.07 mL/mL) + Zinc oxide (.05 mL/mL)CreamTopicalUniversal Cosmetic Co., Ltd2010-08-04Not applicableUs
REVERS Lightening Regimen for the Appearance of Stubborn Dark Marks, Patches and Age Spots Travel SizeAvobenzone + Homosalate + Hydroquinone + Octisalate + OctocryleneKitTopicalRodan & Fields2017-07-24Not applicableUs
REVERSE Lightening Regimen for the Appearance of Stubborn Dark Marks, Patches and Age SpotsAvobenzone + Homosalate + Hydroquinone + Octisalate + OctocryleneKitTopicalRodan & Fields2017-06-01Not applicableUs
Skinprint Ultra Sheer SPF 20Avobenzone (3 g/100g) + Ensulizole (4 g/100g) + Homosalate (15 g/100g) + Octisalate (5 g/100g) + Octocrylene (2.7 g/100g) + Oxybenzone (5 g/100g)LotionTopicalThe Skin Atelier, Inc.2010-10-06Not applicableUs
Skinprint Ultra Sheer SPF 20Avobenzone (1.5 g/100g) + Ensulizole (3 g/100g) + Octinoxate (6 g/100g) + Octocrylene (1.2 g/100g)LotionTopicalThe Skin Atelier, Inc.2009-08-06Not applicableUs
Categories
UNII
G63QQF2NOX
CAS number
70356-09-1
Weight
Average: 310.393
Monoisotopic: 310.156894568
Chemical Formula
C20H22O3
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

Pharmacology

Indication

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

Associated Conditions
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
Toxicity

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

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. MSDS [Link]
  2. article [Link]
  3. wikipedia [Link]
  4. product info [Link]
External Links
PubChem Compound
51040
PubChem Substance
310265226
ChemSpider
46261
ChEBI
134751
ChEMBL
CHEMBL1200522
Wikipedia
Avobenzone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedOtherMelasma1
2CompletedSupportive CareAdvanced Malignant Neoplasm / Dermatologic Complication / Dermatologic Complications / Neoplasms, Malignant1
2Unknown StatusPreventionAtopic Dermatitis (AD)1
2, 3CompletedTreatmentFemale Genital Diseases1
3CompletedSupportive CareDermatologic Complications / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentActinic Keratosis (AK)1
3RecruitingTreatmentAdult Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Childhood Acute Promyelocytic Leukemia With t(15;17)(q22;q12); PML-RARA / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Myeloid Neoplasm1
3RecruitingTreatmentFollicular Lymphoma (FL)1
4CompletedTreatmentHyperpigmentation1
4CompletedTreatmentHypertrophic Cicatrix / Hypertrophic Scars / Keloid Scars1
4CompletedTreatmentMelasma1
4TerminatedNot AvailableSkin Aging1
4Unknown StatusTreatmentPruritis1
Not AvailableCompletedNot AvailableLaryngospasm1
Not AvailableCompletedTreatmentRadiation Induced Fibrosis to the Head and Neck1
Not AvailableCompletedTreatmentStrokes1
Not AvailableUnknown StatusPreventionDermatitis, Eczematous1
Not AvailableUnknown StatusTreatmentPrepubertal Labial Adhesions1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelCutaneous
LotionTopical
CreamTopical
SalveTopical
AerosolTopical
Kit
Cream, augmentedTopical
GelTopical
CreamCutaneous
SprayTopical
ClothTopical
Gel; kit; lotionTopical
Aerosol, foamTopical
LotionTopical30 mg/mL
JellyTopical
Kit; stickTopical
KitTopical
SoapTopical
SprayTopical.64 g/90mL
LipstickTopical
SolutionTopical
OintmentTopical
TabletOral
Aerosol, sprayTopical
KitTopical
SuspensionTopical
CreamTopical100 g/3g
CreamTopical3 g/100g
PowderTopical
Kit; lotionTopical
Cream; kitTopical
StickTopical
EmulsionTopical
LiquidTopical
SprayOral
PasteTopical
Kit
Liquid; sprayTopical
OilTopical
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
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-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1619000000-f818edacf6d19a9f7160
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03dr-3900000000-0c3f2cd90f17bc9fa504

Taxonomy

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
Retro-dihydrochalcone / Alkyl-phenylketone / Butyrophenone / Phenylpropane / Phenylketone / Methoxybenzene / Aryl alkyl ketone / Aryl ketone / Phenoxy compound / Phenol ether
show 14 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on November 30, 2015 12:10 / Updated on June 02, 2018 08:20