U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C28H34O8S2
Molecular Weight 562.698
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ECAMSULE

SMILES

CC1(C)C/2CCC1(CS(=O)(=O)O)C(=O)\C2=C(/[H])\c3ccc(cc3)/C(/[H])=C/4\C5CCC(CS(=O)(=O)O)(C4=O)C5(C)C

InChI

InChIKey=HEAHZSUCFKFERC-IWGRKNQJSA-N
InChI=1S/C28H34O8S2/c1-25(2)21-9-11-27(25,15-37(31,32)33)23(29)19(21)13-17-5-7-18(8-6-17)14-20-22-10-12-28(24(20)30,26(22,3)4)16-38(34,35)36/h5-8,13-14,21-22H,9-12,15-16H2,1-4H3,(H,31,32,33)(H,34,35,36)/b19-13+,20-14+

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://en.wikipedia.org/wiki/Ecamsule

Also called Ecamsule (technical name terephthalylidine dicamphor sulfonic acid), Mexoryl SX is a synthetic sunscreen agent developed and patented by L’Oreal and used in the company’s sunscreen products sold outside the United States since 1993 (approved for use in Europe in 1991). Ecamsule affords broad spectrum protection against the sun’s UVB and UVA rays. Exposed to UV, ecamsule undergoes reversible photoisomerization, followed by photoexcitation. The absorbed UV is then released as thermal energy, without penetrating the skin. The UVB range is 280 to 320 nanometers, and the UVA range is 320 to 400. Ecamsule protects against UV wavelengths in the 290–400 nanometer range, with peak protection at 345 nm.[3][4] Since ecamsule doesn't cover the entire UV spectrum, it should be combined with other active sunscreen agents to ensure broad-spectrum UV protection. Ecamsule is a photostable organic UVA absorber, meaning it doesn't degrade significantly when exposed to light.

Originator

Curator's Comment:: ECAMSULE (Mexoryl) was developed and patented by L’Oreal in 1982 and approved for use in Europe in 1991. To improve its UV coverage and photostability ecamsule has been formulated with avobenzone and octocrylene. This product is marketed in the US as Anthelios SX.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
ANTHELIOS SX

Approved Use

For the prevention of sunburn and for protection against ultraviolet B (UVB) and ultraviolet A (UVA) rays.

Launch Date

1.15344002E12
Preventing
Unknown

Approved Use

Unknown
Preventing
Mexoryl SX

Approved Use

Unknown

Launch Date

6.6268797E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.5 ng/mL
0.576 g 4 times / day multiple, topical
dose: 0.576 g
route of administration: Topical
experiment type: MULTIPLE
co-administered:
ECAMSULE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 % 1 times / day single, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
unknown
n = 2539
Health Status: unknown
Condition: UNK
Sex: M+F
Population Size: 2539
Sources:
Disc. AE: Irritation skin...
AEs leading to
discontinuation/dose reduction:
Irritation skin
Sources:
AEs

AEs

AESignificanceDosePopulation
Irritation skin Disc. AE
2 % 1 times / day single, topical
Recommended
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
unknown
n = 2539
Health Status: unknown
Condition: UNK
Sex: M+F
Population Size: 2539
Sources:
PubMed

PubMed

TitleDatePubMed
Evaluation of the protective effect of sunscreens on in vitro reconstructed human skin exposed to UVB or UVA irradiation.
2000 Mar
A new ecamsule-containing SPF 40 sunscreen cream for the prevention of polymorphous light eruption: a double-blind, randomized, controlled study in maximized outdoor conditions.
2009 Feb
Patents

Sample Use Guides

apply evenly before sun exposure; reapply as needed or after towel drying, swimming, or perspiring
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment:: The evaluation of photoprotection on in vitro reconstructed skin revealed good efficiency for Mexoryl SX (Ecamsule) preparation in preventing UVB-induced damage, as shown by SBC counting and pyrimidine dimer mmunostaining.The efficiency of ECAMSULE applied topically on the skin surface (2 mg/cm2) was assessed regarding specific damage resulting from increasing doses of UVB or UVA.
ECAMSULE applied topically on the skin surface - 2 mg/cm2
Name Type Language
ECAMSULE
INN   MART.   MI   ORANGE BOOK   USAN   USP  
USAN   INN  
Official Name English
ECAMSULE SOLUTION [USP MONOGRAPH]
Common Name English
ECAMSULE [MI]
Common Name English
TEREPHTHALYLIDENE DICAMPHOR SULFONIC ACID [INCI]
Common Name English
(+/-)-(3E,3'E)-3,3'-(P-PHENYLENEDIMETHYLIDYNE)BIS(2-OXO-10-BORNANESULFONIC ACID)
Common Name English
ECAMSULE SOLUTION [USP-RS]
Common Name English
ECAMSULE [USP]
Common Name English
MEXORYL SX
Brand Name English
ECAMSULE COMPONENT OF ANTHELIOS SX
Common Name English
CAPITAL SOLEIL COMPONENT ECAMSULE
Common Name English
ECAMSULE COMPONENT OF CAPITAL SOLEIL
Common Name English
ECAMSULE [INN]
Common Name English
ECAMSULE [MART.]
Common Name English
MEXORYL
Brand Name English
ECAMSULE [WHO-DD]
Common Name English
NSC-760054
Code English
ECAMSULE [USAN]
Common Name English
ECAMSULE [ORANGE BOOK]
Common Name English
ANTHELIOS SX COMPONENT ECAMSULE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C851
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
Code System Code Type Description
INN
7518
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
NCI_THESAURUS
C87221
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
MERCK INDEX
M4807
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
3171
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
DRUG BANK
DB09534
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL2096649
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
PUBCHEM
9915879
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
RXCUI
1544124
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY RxNorm
CAS
92761-26-7
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
FDA UNII
M94R1PM439
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
WIKIPEDIA
ECAMSULE
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY
USP_CATALOG
1231580
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY USP-RS
EVMPD
SUB06443MIG
Created by admin on Fri Jun 25 20:43:16 UTC 2021 , Edited by admin on Fri Jun 25 20:43:16 UTC 2021
PRIMARY