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
Thumb
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.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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.

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
Adverseeffects
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Toxicity

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

Products2
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Banana Boat Dark Tanning Lotion SPF 4Lotion2.5 %TopicalPlaytex Ltd.1994-12-312009-08-06Canada flag
Banana Bt.aloe V.dry Sk.pR.B.lot W/ss.SPF 4Lotion2.7 %TopicalThe Banana Boat Company1994-12-311997-09-02Canada flag
Blue Green Algae With Grape Seed Extract Moisturizer SPF 10Lotion8 %TopicalAubrey Organics Inc.2003-12-022010-09-22Canada flag
Body Satin Lotion 4.85%Lotion4.85 %TopicalMelaleuca, Inc.1994-12-311996-09-10Canada flag
Cap Soleil: Lait Solaire Fps 4Lotion2.5 %TopicalYves Rocher Inc.1998-10-262003-04-30Canada flag
Chap-ice SPF 4 Cherry Lip BalmStick1.5 %TopicalOralabs IncNot applicableNot applicableCanada flag
Chap-ice SPF 4 Original Lip BalmStick1.5 %TopicalOralabs IncNot applicableNot applicableCanada flag
Chapstick Lip Balm 1.5%Stick1.5 %TopicalWhitehall Robins Inc.1992-12-312007-07-20Canada flag
Green Tea and Ginkgo Moisturizer SPF 10Lotion5.75 %TopicalAubrey Organics Inc.2003-12-022010-09-22Canada flag
Grooming Gear After Shave Treatment Lot 2.5%Lotion2.5 %TopicalAmway Corporation1994-12-312001-06-29Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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 flag
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 flag
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 flag
Aruba Aloe Lip Sunscreen and MoisturizerPadimate O (8 g/100g) + Oxybenzone (3 g/100g)LipstickTopicalAruba Aloe Balm NV2011-06-01Not applicableUS flag
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 flag
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 flag
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 flag
Baléa Face Lip Balm SPF 15Padimate O (6.6 % w/w) + Oxybenzone (2.5 % w/w)StickTopicalNorwood Packaging Ltd.2009-07-312015-10-19Canada flag
Banana BoatPadimate O (1.4 g/100g) + Octinoxate (2 g/100g)OilTopicalEdgewell Personal Care Brands Llc2010-09-28Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
Nuquin HpPadimate O (50 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g)GelTopicalStratus Pharmaceuticals1999-09-142015-04-15US flag
Nuquin HpPadimate O (80 mg/1g) + Dioxybenzone (30 mg/1g) + Hydroquinone (40 mg/1g) + Oxybenzone (20 mg/1g)CreamTopicalStratus Pharmaceuticals2003-12-092015-04-09US flag
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 flag
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 flag
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 flag

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
  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. [Article]
  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]
KEGG Drug
D05335
PubChem Compound
30541
PubChem Substance
347827986
ChemSpider
28343
RxNav
32786
ChEBI
135932
ChEMBL
CHEMBL1323699
Wikipedia
Padimate_O
MSDS
Download (47.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
OilTopical
LotionTopical2.7 %
LotionTopical4.85 %
StickTopical1.5 %
JellyTopical
StickTopical
LotionTopical5.75 %
LotionTopical2.5 %
EmulsionTopical
SprayTopical
StickTopical1.5 mg/1g
LipstickTopical
LotionTopical3.5 %
OintmentTopical8 %
LotionTopical
OintmentTopical1.5 %
LotionTopical5 %
LotionTopical1 %
LiquidTopical1 %
GelTopical
CreamTopical
OintmentTopical
SprayTopical8 %
GelTopical4 %
CreamTopical5 %
LotionTopical8 %
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

Drug created at April 06, 2016 21:24 / Updated at October 26, 2021 21:40