Padimate O

Identification

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Name
Padimate O
Accession Number
DB11570
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Padimate O
  • Padimate-O
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Banana Boat Dark Tanning Lotion SPF 4LotionTopicalPlaytex Ltd.1994-12-312009-08-06Canada
Banana Bt.aloe V.dry Sk.pR.B.lot W/ss.SPF 4LotionTopicalThe Banana Boat Company1994-12-311997-09-02Canada
Blue Green Algae With Grape Seed Extract Moisturizer SPF 10LotionTopicalAubrey Organics Inc.2003-12-022010-09-22Canada
Body Satin Lotion 4.85%LotionTopicalMelaleuca, Inc.1994-12-311996-09-10Canada
Cap Soleil: Lait Solaire Fps 4LotionTopicalYves Rocher Inc.1998-10-262003-04-30Canada
Chap-ice SPF 4 Cherry Lip BalmStickTopicalOralabs IncNot applicableNot applicableCanada
Chap-ice SPF 4 Original Lip BalmStickTopicalOralabs IncNot applicableNot applicableCanada
Chapstick Lip Balm 1.5%StickTopicalWhitehall Robins Inc.1992-12-312007-07-20Canada
Green Tea and Ginkgo Moisturizer SPF 10LotionTopicalAubrey Organics Inc.2003-12-022010-09-22Canada
Grooming Gear After Shave Treatment Lot 2.5%LotionTopicalAmway Corporation1994-12-312001-06-29Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Alba Botanica UN-petroleum Cherry SPF18 Lip BalmPadimate O (7.5 g/100g) + Oxybenzone (5.0 g/100g)StickTopicalThe Hain Celestial Group2011-11-02Not applicableUs
Alba Botanica UN-petroleum Tangerine SPF18 Lip BalmPadimate O (7.5 g/100g) + Oxybenzone (5.0 g/100g)StickTopicalThe Hain Celestial Group2011-11-02Not applicableUs
Alba Botanica UN-petroleum Vanilla SPF18 Lip BalmPadimate O (7.5 g/100g) + Oxybenzone (5.0 g/100g)StickTopicalThe Hain Celestial Group2011-11-02Not applicableUs
Ariel Sun Smacker SPF 24 Strawberry KiwiPadimate O (8 g/100g) + Octinoxate (7.5 g/100g) + Oxybenzone (6 g/100g)LipstickTopicalBonne Bell Llc2012-09-06Not applicableUs
Aruba Aloe Lip Sunscreen and MoisturizerPadimate O (8 g/100g) + Oxybenzone (3 g/100g)LipstickTopicalAruba Aloe Balm NV2011-06-01Not applicableUs
Aruba Aloe Very Water Resistant SunscreenPadimate O (42 mg/1mL) + Homosalate (80 mg/1mL) + Octinoxate (70 mg/1mL) + Oxybenzone (30 mg/1mL)LotionTopicalAruba Aloe Balm, Nv2011-06-05Not applicableUs
Aruba Aloe Very Water Resistant Sunscreen - For Faces SPF 30Padimate O (42 mg/1mL) + Homosalate (80 mg/1mL) + Octinoxate (70 mg/1mL) + Oxybenzone (30 mg/1mL)LotionTopicalAruba Aloe Balm NV2011-07-06Not applicableUs
Aruba Aloe Very Water Resistant Sunscreen For Kids SPF 30Padimate O (42 mg/1mL) + Homosalate (80 mg/1mL) + Octinoxate (70 mg/1mL) + Oxybenzone (30 mg/1mL)LotionTopicalAruba Aloe Balm, Nv2011-06-05Not applicableUs
Baléa Face Lip Balm SPF 15Padimate O (6.6 %) + Oxybenzone (2.5 %)StickTopicalNorwood Packaging Ltd.2009-07-312015-10-19Canada
Banana BoatPadimate O (8 g/100g) + Octinoxate (3.5 g/100g) + Oxybenzone (1 g/100g)OilTopicalEdgewell Personal Care, Llc2010-09-282013-12-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Hydroquinone with sunscreensPadimate O (80 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g)CreamTopicalPreferreed Pharmaceuticals Inc.2012-01-302017-01-31Us
Nuquin HpPadimate O (80 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g)CreamTopicalStratus Pharmaceuticals2003-12-092015-04-09Us
Nuquin HpPadimate O (50 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g)GelTopicalStratus Pharmaceuticals1999-09-142015-04-15Us
Perrigo Hydroquinone with sunscreensPadimate O (80 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g)CreamTopicalPerrigo New York Inc.2008-10-232013-04-01Us
Perrigo Hydroquinone with sunscreensPadimate O (50 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g)GelTopicalPerrigo New York Inc.2009-02-042013-01-01Us
Perrigo Hydroquinone with sunscreensPadimate O (80 mg/1g) + Hydroquinone (40 mg/1g) + Octinoxate (40 mg/1g) + Oxybenzone (40 mg/1g)CreamTopicalPerrigo New York Inc.2008-09-232012-09-01Us
Categories
UNII
Z11006CMUZ
CAS number
21245-02-3
Weight
Average: 277.408
Monoisotopic: 277.204179113
Chemical Formula
C17H27NO2
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

Pharmacology

Indication

Indicated as an active UV-B filter to prevent photodamage.

Pharmacodynamics

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.

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

Toxicity

Padimate O causes DNA strand breaks of cells under the epidermis in vitro 1. No LD50 value reported.

Affected organisms
Not Available
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
Not Available

References

General References
  1. 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. [PubMed:10477339]
  2. PADIMATE O - National Library of Medicine HSDB Database [Link]
  3. 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
ChEBI
135932
ChEMBL
CHEMBL1323699
Wikipedia
Padimate_O
AHFS Codes
  • 84:80.00 — Sunscreen Agents
MSDS
Download (47.4 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
OilTopical
KitTopical
StickTopical
JellyTopical
StickTopical
EmulsionTopical
SprayTopical
StickTopical1.5 mg/1g
LipstickTopical
OintmentTopical
LotionTopical
LotionTopical
LiquidTopical
GelTopical
CreamTopical
OintmentTopical
SprayTopical
GelTopical
CreamTopical
LiquidTopical
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)362MSDS
water solubilityInsolubleMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0355 mg/mLALOGPS
logP5.11ALOGPS
logP5.11ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.66 m3·mol-1ChemAxon
Polarizability33.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
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Substituents
Aminobenzoic acid or derivatives / Benzoate ester / Benzoyl / Aniline or substituted anilines / Dialkylarylamine / Tertiary aliphatic/aromatic amine / Amino acid or derivatives / Tertiary amine / Carboxylic acid ester / Carboxylic acid derivative
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Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Drug created on April 06, 2016 15:24 / Updated on September 21, 2019 04:05