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Identification
- Summary
Padimate O is an ingredient used in sunscreens to absorb UV radiation.
- Generic Name
- Padimate O
- DrugBank Accession Number
- DB11570
- Background
Padimate O is an active sunscreen agent in cosmetics and over-the-counter sunscreen drug products in concentrations up to 8%, as regulated by the FDA 3. It is a structurally-related compound to Aminobenzoic acid that absorbs UV-B rays to prevent photodamage. It penetrates human skin, and is shown to induce non-ligatable strand breaks on DNA in vitro and mutagenic effects on yeast in vivo 1.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Padimate O (DB11570)
- Weight
- Average: 277.408
Monoisotopic: 277.204179113 - Chemical Formula
- C17H27NO2
- Synonyms
- Padimate O
- Padimate-O
Pharmacology
- Indication
Indicated as an active UV-B filter to prevent photodamage.
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Padimate O absorbs UV-B rays, which can in turn induce DNA damage in human keratinocytes. While treatment of padimate O suppresses the formation of UV-endonuclease-sensitive sites, there is also an increase in direct strand breaks of DNA in cells 1,2.
- Mechanism of action
It is proposed that simultaneous contact of padimate O with keratinocytes can stimulate the diffusion through human epidermis. Upon photoexcitation, padimate O generates singlet oxygen and forms carbon-centred free radicals. While padimate O attenuates simple and repairable, UV-induced cellular damage, it may also increase complex chemical damage that is more difficult to repair by normal cells 1.
- Absorption
Padimate O is capable of human skin penetration 1.
- Volume of distribution
No pharmacokinetic data available.
- Protein binding
No pharmacokinetic data available.
- Metabolism
No pharmacokinetic data available.
- Route of elimination
No pharmacokinetic data available.
- Half-life
No pharmacokinetic data available.
- Clearance
No pharmacokinetic data available.
- Adverse Effects
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Padimate O causes DNA strand breaks of cells under the epidermis in vitro 1. No LD50 value reported.
- 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.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Banana Boat Dark Tanning Lotion SPF 4 Lotion 2.5 % Topical Playtex Ltd. 1994-12-31 2009-08-06 Canada 
Banana Bt.aloe V.dry Sk.pR.B.lot W/ss.SPF 4 Lotion 2.7 % Topical The Banana Boat Company 1994-12-31 1997-09-02 Canada Blue Green Algae With Grape Seed Extract Moisturizer SPF 10 Lotion 8 % Topical Aubrey Organics Inc. 2003-12-02 2010-09-22 Canada Body Satin Lotion 4.85% Lotion 4.85 % Topical Melaleuca, Inc. 1994-12-31 1996-09-10 Canada Cap Soleil: Lait Solaire Fps 4 Lotion 2.5 % Topical Yves Rocher Inc. 1998-10-26 2003-04-30 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Alba Botanica UN-petroleum Cherry SPF18 Lip Balm Padimate O (7.5 g/100g) + Oxybenzone (5.0 g/100g) Stick Topical The Hain Celestial Group 2011-11-02 Not applicable US 
Alba Botanica UN-petroleum Tangerine SPF18 Lip Balm Padimate O (7.5 g/100g) + Oxybenzone (5.0 g/100g) Stick Topical The Hain Celestial Group 2011-11-02 Not applicable US Alba Botanica UN-petroleum Vanilla SPF18 Lip Balm Padimate O (7.5 g/100g) + Oxybenzone (5.0 g/100g) Stick Topical The Hain Celestial Group 2011-11-02 Not applicable US Ariel Sun Smacker SPF 24 Strawberry Kiwi Padimate O (8 g/100g) + Octinoxate (7.5 g/100g) + Oxybenzone (6 g/100g) Lipstick Topical Bonne Bell Llc 2012-09-06 Not applicable US Aruba Aloe Lip Sunscreen and Moisturizer Padimate O (8 g/100g) + Oxybenzone (3 g/100g) Lipstick Topical Aruba Aloe Balm NV 2011-06-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Hydroquinone with sunscreens Padimate O (80 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) Cream Topical Preferreed Pharmaceuticals Inc. 2012-01-30 2017-01-31 US Nuquin Hp Padimate O (50 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) Gel Topical Stratus Pharmaceuticals 1999-09-14 2015-04-15 US Nuquin Hp Padimate O (80 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g) Cream Topical Stratus Pharmaceuticals 2003-12-09 2015-04-09 US Perrigo Hydroquinone with sunscreens Padimate O (50 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) Gel Topical Perrigo New York Inc. 2009-02-04 2013-01-01 US Perrigo Hydroquinone with sunscreens Padimate O (80 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (40 mg/1g) + Oxybenzone (40 mg/1g) Cream Topical Perrigo New York Inc. 2008-09-23 2012-09-01 US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Benzoic acid esters
- Alternative Parents
- Aminobenzoic acids and derivatives / Dialkylarylamines / Benzoyl derivatives / Aniline and substituted anilines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic oxides show 1 more
- Substituents
- Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Dialkylarylamine show 10 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Z11006CMUZ
- CAS number
- 21245-02-3
- InChI Key
- WYWZRNAHINYAEF-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H27NO2/c1-5-7-8-14(6-2)13-20-17(19)15-9-11-16(12-10-15)18(3)4/h9-12,14H,5-8,13H2,1-4H3
- IUPAC Name
- 2-ethylhexyl 4-(dimethylamino)benzoate
- SMILES
- CCCCC(CC)COC(=O)C1=CC=C(C=C1)N(C)C
References
- General References
- Gulston M, Knowland J: Illumination of human keratinocytes in the presence of the sunscreen ingredient Padimate-O and through an SPF-15 sunscreen reduces direct photodamage to DNA but increases strand breaks. Mutat Res. 1999 Jul 21;444(1):49-60. [Article]
- PADIMATE O - National Library of Medicine HSDB Database [Link]
- FDA - CFR - Code of Federal Regulations Title 21: PART 352 -- SUNSCREEN DRUG PRODUCTS FOR OVER-THE-COUNTER HUMAN USE [STAYED INDEFINITELY] [Link]
- External Links
- KEGG Drug
- D05335
- PubChem Compound
- 30541
- PubChem Substance
- 347827986
- ChemSpider
- 28343
- 32786
- ChEBI
- 135932
- ChEMBL
- CHEMBL1323699
- Wikipedia
- Padimate_O
- MSDS
- Download (47.4 KB)
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Oil Topical Lotion Topical 2.7 % Kit; stick Topical Kit; ointment; stick Topical Lotion Topical 4.85 % Stick Topical 1.5 % Jelly Topical Stick Topical Lotion Topical 5.75 % Lotion Topical 2.5 % Emulsion Topical Spray Topical Stick Topical 1.5 mg/1g Lipstick Topical Lotion Topical 3.5 % Ointment Topical 8 % Lotion Topical Ointment Topical 1.5 % Lotion Topical 5 % Lotion Topical 1 % Liquid Topical 1 % Gel Topical Cream Topical Ointment Topical Spray Topical 8 % Gel Topical 4 % Cream Topical 5 % Lotion Topical 8 % Liquid Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 362 MSDS water solubility Insoluble MSDS - Predicted Properties
Property Value Source Water Solubility 0.0355 mg/mL ALOGPS logP 5.11 ALOGPS logP 5.11 Chemaxon logS -3.9 ALOGPS pKa (Strongest Basic) 2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.54 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 84.66 m3·mol-1 Chemaxon Polarizability 33.73 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes 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 splash10-002r-9240000000-9627a7e80be0a92e3cca Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-2970000000-6a11ca84815d149b1fdc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-006t-2900000000-a20c43040abd93783346 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0092-3940000000-8e45e135813f49683e19 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05al-7900000000-3f490c2118c9037a1540 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01wb-2930000000-25d4e4e7b713e184513f 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]- 172.20758 predictedDeepCCS 1.0 (2019) [M+H]+ 174.56558 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.65874 predictedDeepCCS 1.0 (2019)
Drug created at April 06, 2016 21:24 / Updated at September 08, 2024 21:55