Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H27NO2 |
Molecular Weight | 361.4767 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC(CC)COC(=O)C(C#N)=C(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=FMJSMJQBSVNSBF-UHFFFAOYSA-N
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
DescriptionSources: http://www.thedermreview.com/octocrylene/Curator's Comment: description was created based on several sources, including, http://onlinelibrary.wiley.com/doi/10.1111/cod.12205/epdf
Sources: http://www.thedermreview.com/octocrylene/
Curator's Comment: description was created based on several sources, including, http://onlinelibrary.wiley.com/doi/10.1111/cod.12205/epdf
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.
Originator
Sources: http://www.google.com/patents/US7037511
Curator's Comment: http://143230426296262911.weebly.com/introduction-to-molecule.html
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
2.7 g single, topical dose: 2.7 g route of administration: Topical experiment type: SINGLE co-administered: |
OCTOCRYLENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
2.7 g 4 times / day steady-state, topical dose: 2.7 g route of administration: Topical experiment type: STEADY-STATE co-administered: |
OCTOCRYLENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
43.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
2.7 g 4 times / day steady-state, topical dose: 2.7 g route of administration: Topical experiment type: STEADY-STATE co-administered: |
OCTOCRYLENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse 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 Sources: avobenzone titanium dioxide |
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... |
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 Sources: avobenzone titanium dioxide |
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%) Sources: 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%) |
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 Sources: avobenzone titanium dioxide |
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%) Sources: Eczema (0.4%) Erythema (0.8%) Skin discomfort (0.8%) Sunburn (1.6%) Conjunctivitis (0.4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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 Sources: avobenzone titanium dioxide |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/28704989/ |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Contact allergy to octocrylene. | 2003 Jan |
|
Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography. | 2004 Sep 17 |
|
Sunscreen enhancement of UV-induced reactive oxygen species in the skin. | 2006 Oct 15 |
|
In vitro assessments of UVA protection by popular sunscreens available in the United States. | 2008 Dec |
|
Development of a method for the determination of UV filters in water samples using stir bar sorptive extraction and thermal desorption-gas chromatography-mass spectrometry. | 2008 Feb 1 |
|
Physicochemical study on microencapsulation of hydroxypropyl-beta-cyclodextrin in dermal preparations. | 2010 Jun |
Sample Use Guides
The study was performed in vitro using a Franz type diffusion cell. Only one of the products contained octocrylene and the concentration was 70 g/L (~7%). The sunscreen product was applied to human skin (surface area = 1.13 -1.23 cm2). Following 8-hr topical applications of the products it was reported that no octocrylene was detected in the receptor fluid suggesting that penetration through the skin was minimal to non-existent.
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Classification Tree | Code System | Code | ||
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 217
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CFR |
21 CFR 352.10
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NCI_THESAURUS |
C851
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CFR |
21 CFR 352.20
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OCTOCRYLENE
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DB09535
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ACTIVE MOIETY