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
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
| Molecular Formula | C20H22O3 |
| Molecular Weight | 310.3869 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/ |
832.5 mg 4 times / day multiple, topical dose: 832.5 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/ |
810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.4 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
576 mg 4 times / day multiple, topical dose: 576 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
591.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/ |
832.5 mg 4 times / day multiple, topical dose: 832.5 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
350.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/ |
810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
112.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/ |
832.5 mg 4 times / day multiple, topical dose: 832.5 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
94.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31058986/ |
810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
45.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
810 mg 4 times / day multiple, topical dose: 810 mg route of administration: Topical experiment type: MULTIPLE co-administered: OXYBENZONE |
AVOBENZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
33 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/31058986 |
576 mg 4 times / day multiple, topical dose: 576 mg route of administration: Topical experiment type: MULTIPLE co-administered: OCTOCRYLENE |
AVOBENZONE 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 Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: |
healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: |
Other AEs: Dermatitis, Eczema... |
1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F 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 Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F 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 Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: |
healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: |
| Dermatitis | 2.5% | 3.7 g 1.3 times / day multiple, topical Recommended Dose: 3.7 g, 1.3 times / day Route: topical Route: multiple Dose: 3.7 g, 1.3 times / day Sources: |
healthy, 3.69 years (range: 0.64-48.15 years) Health Status: healthy Age Group: 3.69 years (range: 0.64-48.15 years) Sex: M+F Sources: |
| Rosacea | 0.4% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Taste perversion | 0.4% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Conjunctivitis | 0.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Seborrhea | 0.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Sunburn | 0.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Dry skin | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Eczema | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Erythema | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Skin discomfort | 1.2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Pruritus | 2% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Dermatitis | 2.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Acne | 4.8% | 1.6 g 1.1 times / day multiple, topical Recommended Dose: 1.6 g, 1.1 times / day Route: topical Route: multiple Dose: 1.6 g, 1.1 times / day Sources: |
healthy, 35.44 years (range: 12.04-83.43 years) Health Status: healthy Age Group: 35.44 years (range: 12.04-83.43 years) Sex: M+F Sources: |
| Conjunctivitis | 0.4% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Eczema | 0.4% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Erythema | 0.8% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Skin discomfort | 0.8% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Sunburn | 1.6% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
| Dermatitis | 2.8% | 3.1 g 1.2 times / day multiple, topical Recommended Dose: 3.1 g, 1.2 times / day Route: topical Route: multiple Dose: 3.1 g, 1.2 times / day Sources: |
healthy, 6.69 years (range: 0.5-67.95 years) Health Status: healthy Age Group: 6.69 years (range: 0.5-67.95 years) Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chemical allergens stimulate human epidermal keratinocytes to produce lymphangiogenic vascular endothelial growth factor. | 2015-03-01 |
|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013-09-05 |
|
| Characterization of the UVA protection provided by avobenzone, zinc oxide, and titanium dioxide in broad-spectrum sunscreen products. | 2010-12-01 |
|
| True photoallergy to sunscreens is rare despite popular belief. | 2010-07-22 |
|
| An Assessment of the Efficacy and Safety of CROSS Technique with 100% TCA in the Management of Ice Pick Acne Scars. | 2010-05 |
|
| Determination of organic UV filters in water by stir bar sorptive extraction and direct analysis in real-time mass spectrometry. | 2010-05 |
|
| Filter-filter interactions. Photostabilization, triplet quenching and reactivity with singlet oxygen. | 2010-04 |
|
| A randomized, controlled comparative study of the wrinkle reduction benefits of a cosmetic niacinamide/peptide/retinyl propionate product regimen vs. a prescription 0.02% tretinoin product regimen. | 2010-03 |
|
| Polymorphism and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone. | 2010-02-24 |
|
| Optical and electron paramagnetic resonance studies of the excited states of 4-tert-butyl-4'-methoxydibenzoylmethane and 4-tert-butyl-4'-methoxydibenzoylpropane. | 2009-12-03 |
|
| Photodegradation of dibenzoylmethanes: potential cause of photocontact allergy to sunscreens. | 2009-11 |
|
| Evaluation of spray congealing as technique for the preparation of highly loaded solid lipid microparticles containing the sunscreen agent, avobenzone. | 2009-08 |
|
| Addressing technical challenges associated with the FDA's proposed rules for the UVA in vitro testing procedure. | 2009-06-15 |
|
| A new ecamsule-containing SPF 40 sunscreen cream for the prevention of polymorphous light eruption: a double-blind, randomized, controlled study in maximized outdoor conditions. | 2009-02 |
|
| Impact on facial rejuvenation with dermatological preparations. | 2009 |
|
| Role of UV light in photodamage, skin aging, and skin cancer: importance of photoprotection. | 2009 |
|
| In vitro assessments of UVA protection by popular sunscreens available in the United States. | 2008-12 |
|
| A blocked diketo form of avobenzone: photostability, photosensitizing properties and triplet quenching by a triazine-derived UVB-filter. | 2008-08-05 |
|
| Influence of hydroxypropyl-beta-cyclodextrin on transdermal penetration and photostability of avobenzone. | 2008-06 |
|
| Assessing retinol stability in a hydroquinone 4%/retinol 0.3% cream in the presence of antioxidants and sunscreen under simulated-use conditions: a pilot study. | 2008-03 |
|
| Photostability and efficacy studies of topical formulations containing UV-filters combination and vitamins A, C and E. | 2007-10-01 |
|
| Degradation kinetics of butylmethoxydibenzoylmethane (avobenzone) in aqueous solution. | 2007-10 |
|
| Mexoryl: a review of an ultraviolet a filter. | 2007-09-15 |
|
| OTC product: Anthelios SX. | 2007-09-13 |
|
| I've heard there's a new sunscreen that's supposed to offer better skin protection. Can you tell me more? | 2007-06 |
|
| A new sunscreen agent. | 2007-05-21 |
|
| The FDA approves new over-the-counter sunscreen. | 2007-03-01 |
|
| [Simultaneous determination of 9 ultraviolet absorbers in cosmetics by high-performance liquid chromatography]. | 2007 |
|
| Transient enol isomers of dibenzoylmethane and avobenzone as efficient hydrogen donors toward a nitroxide pre-fluorescent probe. | 2006-11-11 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| Interactions between different solar UVB/UVA filters contained in commercial suncreams and consequent loss of UV protection. | 2006-09 |
|
| Sun protection strength of a hydroquinone 4%/retinol 0.3% preparation containing sunscreens. | 2006-04 |
|
| Changes in ultraviolet absorbance and hence in protective efficacy against lipid peroxidation of organic sunscreens after UVA irradiation. | 2006-03-01 |
|
| Design of a photostabilizer having built-in antioxidant functionality and its utility in obtaining broad-spectrum sunscreen formulations. | 2006-02-24 |
|
| Evaluation of the photostability of different UV filter combinations in a sunscreen. | 2006-01-13 |
|
| A new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane: absorbance stability under solar irradiation. | 2005-02-16 |
|
| Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. | 2005-02 |
|
| Unexpected photolysis of the sunscreen octinoxate in the presence of the sunscreen avobenzone. | 2004-11-25 |
|
| Lack of in vitro protection by a common sunscreen ingredient on UVA-induced cytotoxicity in keratinocytes. | 2004-10-15 |
|
| Sunscreen penetration of human skin and related keratinocyte toxicity after topical application. | 2004-09-28 |
|
| Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography. | 2004-09-17 |
|
| Photochemical behavior of a new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane. | 2004-09-15 |
|
| Non-invasive in vivo determination of UVA efficacy of sunscreens using diffuse reflectance spectroscopy. | 2003-08 |
|
| Bioconvertible vitamin antioxidants improve sunscreen photoprotection against UV-induced reactive oxygen species. | 2003-05-20 |
|
| Protection against UVB irradiation by natural filters extracted from lichens. | 2002-11 |
|
| The effects of derivatives of the nitroxide tempol on UVA-mediated in vitro lipid and protein oxidation. | 2002-07-01 |
|
| The effect of UV absorbing sunscreens on the reflectance and the consequent protection of skin. | 2002-02 |
|
| A new model using liposomes that allow to distinguish between absorption and oxidative properties of sunscreens. | 2002-01 |
|
| Photochemical studies of 4-tert-butyl-4'-methoxydibenzoylmethane (BM-DBM). | 2001-11-15 |
|
| Multiple chemical sensitivities, including iatrogenic allergic contact dermatitis, in a patient with chronic actinic dermatitis: implications for management. | 1996-09 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:56:01 GMT 2025
by
admin
on
Mon Mar 31 17:56:01 GMT 2025
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| Record UNII |
G63QQF2NOX
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
142401
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NCI_THESAURUS |
C851
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CFR |
21 CFR 352.10
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| Code System | Code | Type | Description | ||
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SUB05617MIG
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45045
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AA-89
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AVOBENZONE
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6480
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CHEMBL1200522
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m2151
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1045337
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C47406
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DB09495
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100000086882
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