Octocrylene

Identification

Summary

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

Brand Names
Meijer
Generic Name
Octocrylene
DrugBank Accession Number
DB09535
Background

Octocrylene is a compound often used as an additive in sun screen, and is thought to have skin moisturizing effects because of its emollient properties. What makes this chemical such a popular additive to sun block, is its ability to neutralize UV radiation dissipated by sunlight, and to minimize skin damage from prolonged sun exposure. Octocrylene is also often combined with avobenzone, another common sunscreen ingredient often appearing on ingredient labels. Because of its effectiveness, the chemical has been approved across the globe for use in cosmetics and skin care products, but the concentrations of this ingredient are usually limited to no more than 10 or 12 percent. However, the use of this chemical doesn’t just stop with sunscreen for face and arms, but can extend to a variety of other products, like hair spray, tannin oil, BB cream, conditioner, and CC cream, among others. Octocrylene may cause contact and photocontact allergy.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 361.485
Monoisotopic: 361.204179113
Chemical Formula
C24H27NO2
Synonyms
  • Octocrileno
  • Octocrilenum
  • Octocrylene

Pharmacology

Indication

In the US, Octocrylene has been evaluated by the FDA and is considered safe for use up to 10% in the formula. Similarly, the EU allows its use up to 10% in a formula while Health Canada allows a maximum use level of 12%.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Octocrylene is an effective oil soluble liquid UV‐B filter. It has excellent dissolving properties for crystalline UV filters. Due to its outstanding photostability it is used as photostabilizer. Conjugated acrylate portion absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths in the range of 280-320 nm which protects the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, which functions as an emollient due to it's hydrophobicity.

TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHumans
UEstrogen receptor betaNot AvailableHumans
Absorption

Ecamsule is used topically, it not absorbed or metabolized.

Volume of distribution

Ecamsule is only used topically, it not absorbed.

Protein binding

Ecamsule is only used topically, it not absorbed.

Metabolism

Ecamsule is used topically, it not absorbed.

Route of elimination

Ecamsule is used topically, it not absorbed.

Half-life

Ecamsule is only used topically, it does not have half life

Clearance

Ecamsule is used topically, it not absorbed or metabolized.

Adverse Effects
Medicalerrors
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Toxicity

Octocrylene is one of those ingredients that can be absorbed into the skin and some studies have shown that it may promote generation of potentially harmful free radicals when exposed to light. Since free radicals can damage DNA, there is concern that this ingredient might have contributed to an increased incidence of melanoma in sunscreen-users compared to non-users.

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

Products
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Panama Jack SPF 4Lotion19.12 mg/1mLTopicalPrime Enterprises Inc.2019-02-01Not applicableUS flag
Panama Jack SPF 4 Dark Tanning OilOil16.72 mg/1mLTopicalPrime Enterprises Inc.2019-03-04Not applicableUS flag
Scarsystem Scar GelGel3.8 %TopicalSystem Biologie AgNot applicableNot applicableCanada flag
UV Defense Pocket Sun Block Tissues (Broad Spectrum, SPF30)Liquid9.5 g/100gTopicalC&tech Corporation2018-03-012018-03-25US flag
UV Defense Pocket Sun Pad (Broad Spectrum, SPF30)Liquid9.5 g/100gTopicalC&tech Corporation2018-03-012018-03-25US flag
W.skin Triple Care SunStick8.5 g/100gTopicalJ&J COMPANY2021-05-08Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
02 Cushion Spf45 SunscreenOctocrylene (2.5 g/100mL) + Octinoxate (5 g/100mL) + Octisalate (5 g/100mL) + Titanium dioxide (13.5 g/100mL) + Zinc oxide (8 g/100mL)LiquidTopicalCOIZ CO LTD2019-06-30Not applicableUS flag
100 SPF CreamOctocrylene (10 % w/w) + Avobenzone (3 % w/w) + Homosalate (15 % w/w) + Octisalate (5 % 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 18Octocrylene (50 mg/1mL) + Avobenzone (25 mg/1mL) + Octisalate (50 mg/1mL)LotionTopicalAndalou Naturals2014-03-01Not applicableUS flag
14-day Skin Rescue SPF 30Octocrylene (2.35 % w/w) + Avobenzone (3 % w/w) + Homosalate (4 % w/w) + Octisalate (5 % w/w) + Oxybenzone (6 % w/w)CreamTopicalJohnson & Johnson2009-02-162013-07-31Canada flag
15 Continuous Spray Sunscreen With Instant BronzerOctocrylene (1.85 %) + Avobenzone (2 %) + Octisalate (5 %)SprayTopicalPrime Enterprises, Inc.2018-04-092020-03-01Canada flag
15 SPF Fps Premium SunscreenOctocrylene (10 % w/w) + Avobenzone (3 % w/w) + Ensulizole (2 % w/w) + Oxybenzone (2 % w/w)LotionTopicalEmpack Spraytech Inc2005-05-04Not applicableCanada flag
15 SPF Fps Sunscreen Lotion Écran SolaireOctocrylene (3.0 % w/w) + Avobenzone (0.9 % w/w) + Oxybenzone (3.0 % w/w)LotionTopicalEnergizer Canada Inc2007-03-012011-07-29Canada flag
15 SPF Sunscreen Uva/uvb Protection Oil-free Milky SprayOctocrylene (2.0 %) + Avobenzone (3.0 %) + Octinoxate (5.0 %) + Octisalate (3.0 %) + Oxybenzone (2.0 %)EmulsionTopicalCoty Canada Inc.2009-02-232013-07-24Canada flag
15 SPF Sunscreen Uva/uvb Protection Vitalizing Age-defying CreamOctocrylene (2.0 %) + Avobenzone (3.0 %) + Octinoxate (7.5 %) + Octisalate (5.0 %) + Oxybenzone (3.0 %)CreamTopicalCoty Canada Inc.2009-02-232013-07-24Canada flag
15 Spray Gel Sunscreen With Instant BronzerOctocrylene (1.85 %) + Avobenzone (2 %) + Octisalate (5 %) + Oxybenzone (0.5 %)GelTopicalPrime Enterprises, Inc.2018-04-092020-03-31Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Abalone Crystaldouble EX BbOctocrylene (3 g/100mL) + Adenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL) + Octinoxate (2 g/100mL) + Titanium dioxide (9.9 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-03-10Not applicableUS flag
BEYOND THE SHAVE For MenOctocrylene (2.7 g/100mL) + Allantoin (0.5 g/100mL) + Avobenzone (3.0 g/100mL) + Dimethicone (2.9 g/100mL) + Homosalate (2.5 g/100mL) + Octasulfur (3.0 g/100mL) + Octisalate (5 g/100mL)KitTopicalRodan & Fields2017-06-01Not applicableUS flag
CoreTex Professional Outdoor Skin Protection WalletOctocrylene (2.5 g/100mL) + Avobenzone (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) + Oxybenzone (6 g/100mL) + Oxybenzone (6 g/100g) + Oxybenzone (6 g/100mL) + Synthetic camphor (0.1 g/100mL) + Zinc acetate dihydrate (1 g/100mL)TopicalCoreTex Products2019-11-27Not applicableUS flag
D-one By Tamdoan Bb LightOctocrylene (1 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2016-02-232016-09-05US flag
D-one By Tamdoan Bb MediumOctocrylene (1 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2019-11-19Not applicableUS flag
D-one By Tamdoan Sunscreen 50Octocrylene (1 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g)CreamTopicalDran Co.,ltd2019-11-19Not applicableUS flag
Dr.althea Aurora Cover Cushion 21Octocrylene (2 g/100g) + Adenosine (0.04 g/100g) + Nicotinamide (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (4.8 g/100g) + Titanium dioxide (9.00552 g/100g) + Zinc oxide (2 g/100g)LiquidTopicalDr. Althea2017-04-032018-11-22US flag
Glytone Clarifying SunVanish with SunscreenOctocrylene (18.6 mg/1g) + Avobenzone (20 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (75 mg/1g) + Oxybenzone (50 mg/1g)CreamTopicalGenesis Pharmaceutical, Inc.2012-06-132018-02-28US flag
Glytone SunVanish Skin LighteningOctocrylene (18.6 mg/1g) + Avobenzone (20 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (75 mg/1g) + Oxybenzone (50 mg/1g)CreamTopicalPierre Fabre USA Inc.2012-06-132021-09-30US flag
MediSpa SunSpray sunblockOctocrylene (0.01 mL/1mL) + Enzacamene (0.05 mL/1mL) + Octinoxate (0.075 mL/1mL)SprayTopicalUniversal Cosmetic Co., Ltd2010-08-06Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5A68WGF6WM
CAS number
6197-30-4
InChI Key
FMJSMJQBSVNSBF-UHFFFAOYSA-N
InChI
InChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3
IUPAC Name
2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate
SMILES
CCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C1=CC=CC=C1

References

General References
  1. Hanson KM, Gratton E, Bardeen CJ: Sunscreen enhancement of UV-induced reactive oxygen species in the skin. Free Radic Biol Med. 2006 Oct 15;41(8):1205-12. Epub 2006 Jul 6. [Article]
  2. Drug Information [Link]
  3. Skin care research [Link]
PubChem Substance
347910458
ChemSpider
21165
BindingDB
74416
RxNav
77674
ChEBI
135526
ChEMBL
CHEMBL1201147
Wikipedia
Octocrylene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentBMI >30 kg/m2 / Weight Loss1
4Active Not RecruitingTreatmentOsteoporotic Fractures / Postmenopausal Osteoporosis1
4Active Not RecruitingTreatmentPercutaneous Coronary Intervention (PCI)1
4Active Not RecruitingTreatmentPneumonia1
4Active Not RecruitingTreatmentRespiratory Muscle Weakness / Spinal Cord Injuries (SCI)1
4Active Not RecruitingTreatmentRheumatoid Arthritis1
4Active Not RecruitingTreatmentSmoking, Cessation1
4CompletedNot AvailableChronic Heart Failure (CHF)1
4CompletedNot AvailableDrug Safety1
4CompletedBasic ScienceAsthma / Healthy Volunteers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GelCutaneous
PasteTopical
Cream, augmentedTopical
Spray, suspensionTopical
KitOral; Topical
JellyTopical
PowderTopical
GelTopical
SalveTopical
KitTopical
Gel; kit; lotionTopical
OintmentTopical
Kit; stickTopical
SpongeTopical
OilTopical
LotionTopical
SprayTopical
StickTopical
SuspensionTopical
LotionTopical19.12 mg/1mL
OilTopical16.72 mg/1mL
Kit; lotionTopical
Cream; kitTopical
Jelly; kitTopical
GelTopical3.8 %
AerosolTopical
CreamCutaneous; Topical
SprayOral
EmulsionTopical
SoapTopical
CreamTopical
LotionOral
SolutionTopical
Aerosol, foamTopical
Aerosol, sprayTopical
LiquidTopical9.5 g/100g
StickTopical8.5 g/100g
LiquidTopical
LipstickTopical
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00157 mg/mLALOGPS
logP6.23ALOGPS
logP6.78ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area50.09 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.58 m3·mol-1ChemAxon
Polarizability41.43 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [Article]

Drug created on November 30, 2015 19:10 / Updated on July 29, 2021 06:27