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Details

Stereochemistry RACEMIC
Molecular Formula C17H27NO2
Molecular Weight 277.4018
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PADIMATE O

SMILES

CCCCC(CC)COC(=O)C1=CC=C(C=C1)N(C)C

InChI

InChIKey=WYWZRNAHINYAEF-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C17H27NO2
Molecular Weight 277.4018
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: http://www.skincancer.org/prevention/sun-protection/sunscreen/the-skin-cancer-foundations-guide-to-sunscreens http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=352.50 http://www.ncbi.nlm.nih.gov/pubmed/10477339

Padimate O is an organic compound related to the water-soluble compound PABA (4-aminobenzoic acid) that is used as an ingredient in some sunscreens. this chemical releases free radicals, damages DNA, has estrogenic activity, and causes allergic reactions in some people. Maximum FDA-approved concentration - 8%. Range of protection - UVB.

Originator

Willstätter, R.|Kahn, W.
1
Sources: DOI: 10.1002/cber.19040370172

Approval Year

1964
103
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
Unknown

Approved Use

Lightens dark discolorations in the skin such as age spots, liver spots, freckles, minor scars and pigment in skin that may occur during pregnancy or from the use of oral contraceptives. Helps prevent sunburn.
Doses

Doses

DosePopulationAdverse events​
10 % single, topical
Highest studied dose
Dose: 10 %
Route: topical
Route: single
Dose: 10 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/9249286/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9249286/
Other AEs: Contact dematitis...
Other AEs:
Contact dematitis
Sources:
https://pubmed.ncbi.nlm.nih.gov/9249286/
AEs

AEs

AESignificanceDosePopulation
Contact dematitis
10 % single, topical
Highest studied dose
Dose: 10 %
Route: topical
Route: single
Dose: 10 %
Sources:
https://pubmed.ncbi.nlm.nih.gov/9249286/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9249286/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP19A1
429

UMAT
30

CYP2C19
2057

P-gp
1741
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 inconclusive [IC50 10.684 uM]
CYP19A1
430
 no
P-gp
1932
 no
UMAT
30
 no
CYP2C9
2497
 yes [IC50 13.4504 uM]
CYP1A2
2333
 yes [IC50 4.5646 uM]
CYP2C19
2141
 yes [IC50 6.9178 uM]
CYP3A4
2633
 yes [IC50 7.5637 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Dispersive liquid-liquid microextraction followed by gas chromatography-mass spectrometry for the rapid and sensitive determination of UV filters in environmental water samples.
2010-09
Photostability and phytotoxicity of selected sunscreen agents and their degradation mixtures in water.
2009-11
Determination of ink photoinitiators in packaged beverages by gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry.
2008-06-20
Determination of 2-isopropyl thioxanthone and 2-ethylhexyl-4-dimethylaminobenzoate in milk: comparison of gas and liquid chromatography with mass spectrometry.
2007-09
Fluorescence of sunscreens adsorbed to dielectric nanospheres: parallels to optical behavior on hacat cells and skin.
2006-09-28
Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography.
2004-09-17
Optical spectroscopy of hydrophobic sunscreen molecules adsorbed to dielectric nanospheres.
2004-06
Patents

Patents

JP2007537173A
1
JP4829795B2
1
JPH08165222A
1

Sample Use Guides

In Vivo Use Guide
Apply liberally 15 minutes before sun exposure. At least every 2 hours
Route of Administration: Topical
In Vitro Use Guide
Padimate-O reduces direct DNA damage in human keratinocytes from sunlight (UV-endonuclease-sensitive sites) from 4.32 to 1.52 (given as the number/megabase/kJ/m2).
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:14 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:14 GMT 2025
Record UNII
Z11006CMUZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PADIMATE O
HSDB   MART.   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
ETHYLHEXYL DIMETHYL PABA
INCI  
INCI  
Preferred Name English
PADIMATE O [VANDF]
Common Name English
ARLATONE UVB
Brand Name English
2-ETHYLHEXYL 4-(DIMETYLAMINO)BENZOATE
Common Name English
OCTYL DIMETHYL PABA [VANDF]
Common Name English
2-ETHYL-HEXYL 4-DIMETHYLAMINOBENZOATE
Systematic Name English
PADIMATE O [USAN]
Common Name English
Padimate o [WHO-DD]
Common Name English
OCTYL DIMETHYL PABA
VANDF  
Common Name English
BENZOIC ACID, 4-(DIMETHYLAMINO)-, 2-ETHYLHEXYL ESTER
Common Name English
UVASORB DMO
Brand Name English
PADIMATE O [USP MONOGRAPH]
Common Name English
PADIMATE O, (±)-
Common Name English
4-(DIMETHYLAMINO)BENZOIC ACID 2-ETHYLHEXYL ESTER [MI]
Common Name English
PADIMATE O [HSDB]
Common Name English
2-ETHYLHEXYL N,N-DIMETHYL-P-AMINOBENZOATE
Common Name English
PADIMATE-O
VANDF  
Common Name English
EUSOLEX 6007
Brand Name English
PADIMATE-O [VANDF]
Common Name English
PAMIMATE O [VANDF]
Common Name English
4-(DIMETHYLAMINO)BENZOIC ACID 2-ETHYLHEXYL ESTER
MI  
Systematic Name English
2-ETHYLHEXYL P-(DIMETHYLAMINO)BENZOATE
Common Name English
PADIMATE O [MART.]
Common Name English
ESCALOL 507
Brand Name English
PADIMATE O [USP-RS]
Common Name English
2-Ethylhexyl 4-(dimethylamino)benzoate
Systematic Name English
(±)-PADIMATE O
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C851
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
Code System Code Type Description
MERCK INDEX
m4524
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY Merck Index
HSDB
7169
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
244-289-3
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
RS_ITEM_NUM
1491503
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL1323699
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
FDA UNII
Z11006CMUZ
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
EVMPD
SUB169711
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
DRUG CENTRAL
4270
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
DAILYMED
Z11006CMUZ
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
WIKIPEDIA
PADIMATE O
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
CAS
21245-02-3
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
SMS_ID
100000159525
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
DRUG BANK
DB11570
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID7029320
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
PUBCHEM
30541
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
NCI_THESAURUS
C84038
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
EVMPD
SUB14742MIG
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
MESH
C041981
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY
RXCUI
32786
Created by admin on Mon Mar 31 17:34:14 GMT 2025 , Edited by admin on Mon Mar 31 17:34:14 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of N-nitroso-desmethyl-padimate o
IMPURITY -> PARENT
Related Record Type Details
Structure of PADIMATE O
ACTIVE MOIETY
NIH
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