Identification
- Generic Name
- Diethylamino hydroxybenzoyl hexyl benzoate
- DrugBank Accession Number
- DB11269
- Background
Diethylamino hydroxybenzoyl hexyl benzoate is a UV filter with high absorption in the UV-A range. Minimizing the overexposure of human skin to ultraviolet radiation that may lead to acute and chronic photodamage, diethylamino hydroxybenzoyl hexyl benzoate is an oil-soluble UV filter that may be incorporated in the oil phase of emulsions 5. Diethylamino hydroxybenzoyl hexyl benzoate was approved in Europe in 2005, and is also marketed in the U.S., South America, Mexico, Japan and Taiwan. It has a chemical structure similar to the classical benxophoenone drug class, and displays good photostability 1. It is used in concentrations up to 10% in sunscreen products, either alone or in combination with other UV absorbers 5.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Diethylamino hydroxybenzoyl hexyl benzoate (DB11269)
- Weight
- Average: 397.515
Monoisotopic: 397.225308482 - Chemical Formula
- C24H31NO4
- Synonyms
- Hexyl 2-(4-(diethylamino)-2-hydroxybenzoyl)benzoate
Pharmacology
- Indication
Indicated for use as a sunscreen agent.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Sunburn ••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Diethylamino hydroxybenzoyl hexyl benzoate is an organic UV filter that attenuates the exposure of UV radiation on human skin 2. In vitro, topical application of diethylamino hydroxybenzoyl hexyl benzoate exerted an anti-inflammatory effect on inflammation-evoked mouse ears by inhibiting oedema formation 3.
- Mechanism of action
Diethylamino hydroxybenzoyl hexyl benzoate absorbs in the UV-A range with the peak at 354 nm 1.
- Absorption
Based on the findings of a rat study assessing dermal or percutaneous absorption, only a minor amount of diethylamino hydroxybenzoyl hexyl benzoate will undergo percutaneous absorption and most of the compounds will remain in the upper layers of the stratum corneum 5. In rat and porcine skin, the percutaneous absorption was 0.10 ± 0.12 μg/cm^2 or 0.04 ± 0.05% 5.
- Volume of distribution
No pharmacokinetic data.
- Protein binding
No pharmacokinetic data.
- Metabolism
In steady-state and transient photolysis experiments in vitro, diethylamino hydroxybenzoyl hexyl benzoate may be oxidized by H2O2/UV to form degradation products 2. Like other UV filters, diethylamino hydroxybenzoyl hexyl benzoate may be subject to photodegradation upon absorption of UV radiation, which results in the compound passing from a ground state to either a singlet or triplet excited state 1.
- Route of elimination
No pharmacokinetic data.
- Half-life
No pharmacokinetic data.
- Clearance
No pharmacokinetic data.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
In a rat acute oral toxicity study, median LD50 value was reported to be >2000 mg/kg.4 No case of overdose has been reported. Diethylamino hydroxybenzoyl hexyl benzoate was not shown to be mutagenic, clastogenic, or phototoxic in vitro 5. The no observed adverse effect level (NOAEL) 200 mg/kg bw/day for maternal toxicity, and 1000 mg/kg bw/day (highest applied dose) for prenatal developmental toxicity 5.
- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Uvinul A Plus (BASF)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Age 20s ESSENCE COVER PACT WHITE DARK BE-35 Diethylamino hydroxybenzoyl hexyl benzoate (0.375 g/12.5g) + Octinoxate (0.875 g/12.5g) + Octocrylene (0.5 g/12.5g) + Titanium dioxide (0.8825 g/12.5g) Cream Topical Aekyung Industrial Co., Ltd. 2017-06-02 2020-01-13 US 
Age 20s ESSENCE COVER PACT WHITE DEEP BE-25 Diethylamino hydroxybenzoyl hexyl benzoate (0.375 g/12.5g) + Octinoxate (0.875 g/12.5g) + Octocrylene (0.5 g/12.5g) + Titanium dioxide (0.8825 g/12.5g) Cream Topical Aekyung Industrial Co., Ltd. 2017-06-02 2020-01-13 US BRING GREEN Tea Tree CICA Cooling Sun Diethylamino hydroxybenzoyl hexyl benzoate (3.5 g/100g) + Bemotrizinol (1.5 g/100g) + Octyl triazone (3.0 g/100g) + Polysilicone-15 (2.0 g/100g) Stick Topical CJ Olive Young Corporation 2022-08-01 Not applicable US Calming Days Vegan Sunscreen Diethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Bisoctrizole (2 g/100mL) + Iscotrizinol (1.2 g/100mL) + Octyl triazone (2.4 g/100mL) Gel Topical Merci Co. 2022-10-18 Not applicable US CC Cream SPF 50 Diethylamino hydroxybenzoyl hexyl benzoate (2.6 mg/5000mg) + Octyl triazone (0.26 mg/5000mg) + Titanium dioxide (0.83 mg/5000mg) Cream Cutaneous; Topical FRIDDA DORSCH SL 2021-04-07 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BRING GREEN Tea Tree CICA Cooling Sun Diethylamino hydroxybenzoyl hexyl benzoate (3.5 g/100g) + Bemotrizinol (1.5 g/100g) + Octyl triazone (3.0 g/100g) + Polysilicone-15 (2.0 g/100g) Stick Topical CJ Olive Young Corporation 2022-08-01 Not applicable US Calming Days Vegan Sunscreen Diethylamino hydroxybenzoyl hexyl benzoate (3 g/100mL) + Bisoctrizole (2 g/100mL) + Iscotrizinol (1.2 g/100mL) + Octyl triazone (2.4 g/100mL) Gel Topical Merci Co. 2022-10-18 Not applicable US D-one By Tamdoan Bb Light Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g) Cream Topical Dran Co.,ltd 2016-02-23 2016-09-05 US D-one By Tamdoan Bb Medium Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g) Cream Topical Dran Co.,ltd 2019-11-19 Not applicable US D-one By Tamdoan Sunscreen 50 Diethylamino hydroxybenzoyl hexyl benzoate (2 g/100g) + Adenosine (0.04 g/100g) + Arbutin (2 g/100g) + Octinoxate (7 g/100g) + Octisalate (5 g/100g) + Octocrylene (1 g/100g) + Titanium dioxide (2.54 g/100g) + Zinc oxide (5.99 g/100g) Cream Topical Dran Co.,ltd 2019-11-19 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzophenones
- Direct Parent
- Benzophenones
- Alternative Parents
- Diphenylmethanes / Aryl-phenylketones / Benzoic acid esters / m-Aminophenols / Dialkylarylamines / Benzoyl derivatives / Aniline and substituted anilines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids show 4 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Amino acid or derivatives / Aminophenol / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl ketone / Aryl-phenylketone / Benzoate ester show 19 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- ANQ870JD20
- CAS number
- 302776-68-7
- InChI Key
- FDATWRLUYRHCJE-UHFFFAOYSA-N
- InChI
- InChI=1S/C24H31NO4/c1-4-7-8-11-16-29-24(28)20-13-10-9-12-19(20)23(27)21-15-14-18(17-22(21)26)25(5-2)6-3/h9-10,12-15,17,26H,4-8,11,16H2,1-3H3
- IUPAC Name
- hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate
- SMILES
- CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(C=C1O)N(CC)CC
References
- General References
- Kawakami CM, Maximo LN, Fontanezi BB, da Silva RS, Gaspar LR: Diethylamino hydroxybenzoyl hexyl benzoate (DHHB) as additive to the UV filter avobenzone in cosmetic sunscreen formulations - Evaluation of the photochemical behavior and photostabilizing effect. Eur J Pharm Sci. 2017 Mar 1;99:299-309. doi: 10.1016/j.ejps.2016.12.031. Epub 2016 Dec 30. [Article]
- Gong P, Yuan H, Zhai P, Dong W, Li H: Degradation of organic ultraviolet filter diethylamino hydroxybenzoyl hexyl benzoate in aqueous solution by UV/H2O2. Environ Sci Pollut Res Int. 2015 Jul;22(13):10189-95. doi: 10.1007/s11356-015-4166-7. Epub 2015 Feb 20. [Article]
- Couteau C, Chauvet C, Paparis E, Coiffard L: UV filters, ingredients with a recognized anti-inflammatory effect. PLoS One. 2012;7(12):e46187. doi: 10.1371/journal.pone.0046187. Epub 2012 Dec 20. [Article]
- EMA Scientific Committee on Consumer Products (SCCP): OPINION ON Diethylamino hydroxybenzoyl hexyl benzoate [Link]
- European Commission: OPINION ON Diethylamino hydroxybenzoyl hexyl benzoate [File]
- External Links
- ChemSpider
- 8286957
- 1426392
- ChEBI
- 136006
- ZINC
- ZINC000034230491
- Wikipedia
- Diethylamino_hydroxybenzoyl_hexyl_benzoate
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lotion Topical Gel Topical Stick Topical Cream Topical Cream Cutaneous; Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 54, Decomposes at 314 European Commission SCCP/1166/08 water solubility < 0.01 mg/L European Commission SCCP/1166/08 logP 6.2 European Commission SCCP/1166/08 - Predicted Properties
Property Value Source Water Solubility 0.00702 mg/mL ALOGPS logP 6.03 ALOGPS logP 6.82 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 7.29 Chemaxon pKa (Strongest Basic) 3.38 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 66.84 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 117.64 m3·mol-1 Chemaxon Polarizability 45.58 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-1098000000-6ad197a71dc3917ac7fa Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fr2-0059000000-0272ca62b613d0cf7525 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0159-0195000000-666be468da732f612ca7 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05mk-4292000000-2f74ebc1c6c91ff350d7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0159-2493000000-e72d6b4ad8cb3577e2b0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-9553000000-472d631f98dfd865331d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 215.3648838 predictedDarkChem Lite v0.1.0 [M-H]- 204.3185 predictedDeepCCS 1.0 (2019) [M+H]+ 214.6541838 predictedDarkChem Lite v0.1.0 [M+H]+ 207.24377 predictedDeepCCS 1.0 (2019) [M+Na]+ 215.2461838 predictedDarkChem Lite v0.1.0 [M+Na]+ 214.8091 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at March 27, 2024 05:12