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Chemistry

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Also known as: Ecamsule, 92761-26-7, Nsc-760054, Ecamsule (usp/inn), Schembl100469, Hms3264d09
Molecular Formula
C28H34O8S2
Molecular Weight
562.7  g/mol
InChI Key
HEAHZSUCFKFERC-AXPXABNXSA-N

Terephthalylidene Dicamphor Sulfonic Acid
1 2D Structure

Terephthalylidene Dicamphor Sulfonic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(3Z)-3-[[4-[(Z)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid
2.1.2 InChI
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-
2.1.3 InChI Key
HEAHZSUCFKFERC-AXPXABNXSA-N
2.1.4 Canonical SMILES
CC1(C2CCC1(C(=O)C2=CC3=CC=C(C=C3)C=C4C5CCC(C4=O)(C5(C)C)CS(=O)(=O)O)CS(=O)(=O)O)C
2.1.5 Isomeric SMILES
CC1(C2(C(=O)/C(=C\C3=CC=C(C=C3)/C=C/4\C(=O)C5(C(C4CC5)(C)C)CS(=O)(=O)O)/C1CC2)CS(=O)(=O)O)C
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 3,3'-(1,4-phenylenedimethylidyne)bis(7,7-dimethyl-2-oxobicyclo(2.2.1)heptane-1-methanesulfonic Acid)

2. Ecamsule

3. Terephthalylidene Dicamphor Sulfonic Acid

2.2.2 Depositor-Supplied Synonyms

1. Ecamsule

2. 92761-26-7

3. Nsc-760054

4. Ecamsule (usp/inn)

5. Schembl100469

6. Hms3264d09

7. Pharmakon1600-01503832

8. Nsc760054

9. Akos015900169

10. Ccg-213204

11. [(2z)-2-[[4-[(z)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic Acid

12. Hy-16182

13. Cs-0006179

14. D03932

15. E83896

16. Ab01563286_01

17. Sr-01000944180

18. Q5332142

19. Sr-01000944180-1

20. Terephthalylidene-3,3'-dicamphor-10,10'-disulfonic Acid

21. 3,3',3,3'-(p-phenylenebismethylidyne)bis(2-oxo-7,7-dimethylbicyclo[2.2.1]heptane-1-methanesulfonic Acid)

2.3 Create Date
2006-04-28
3 Chemical and Physical Properties
Molecular Weight 562.7 g/mol
Molecular Formula C28H34O8S2
XLogP33.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count6
Exact Mass562.16951039 g/mol
Monoisotopic Mass562.16951039 g/mol
Topological Polar Surface Area160 Ų
Heavy Atom Count38
Formal Charge0
Complexity1230
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count4
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Ultraviolet screen

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 639


/EXPL THER/ The aim of this study was to determine, for regulatory purposes, the potential of Mexoryl SX, a broad UVA absorber that also absorbs to some extent in the UVB, to modify the UV radiation (UVR)-induced murine skin tumor development and growth. Skh-hr1 mice were exposed to solar-simulated UVR 5 days per week for 40 weeks. Two control groups were irradiated without topical application, three groups received a sunscreen preparation containing either the UVA absorber, Mexoryl SX at 5 or 10% concentration, or a filter that absorbs principally in the UVB, 2-ethylhexyl-p-methoxycinnamate (2-EHMC) at 5% concentration, introduced as a comparator test article. Sunscreen application was performed before UVR exposure 3 days per week and after UVR exposure on the other 2 days (consistent with the design of a standard photocarcinogenesis safety test). Two different weekly UVR doses were administrated: the lower dose was given to one group of unprotected animals, whereas the higher dose was administrated to the other unprotected group and to the three sunscreen-treated groups. The two UVR control groups demonstrated a UVR-dependent response for cumulative tumor prevalence, tumor yield and median latent period. Neither concentration of Mexoryl SX increased the probability of tumor development; consistent with the principles for safety testing, this provides evidence in that it is safe for use in sunlight. Although this study was explicitly designed as a safety test, the results also provide some clues about the efficacy of Mexoryl SX in decreasing the probability of tumor development. Topical administration of Mexoryl SX, at both concentrations, resulted in a 6 week delay in the median latent period compared to high UVR controls, whereas 5% 2-EHMC delayed the median latent periods only by 2 weeks. Tumor prevalence and yield show the same efficacy differences between the two sunscreen ingredients. Tumor protection factors were calculated from these results and found to be equal to 2.4 for the two preparations containing Mexoryl SX and to 1.3 for the 5% 2-EHMC preparation. These findings illustrate the efficacy of Mexoryl SX in preventing UVR-induced carcinogenesis.

PMID:8863475 Fourtanier A; Photochem Photobiol 64 (4): 688-93 (1996)


/EXPL THER/ In a previous study on the hairless mouse it was shown that sub-erythemal doses of pure UV-A enhanced the numerous changes normally observed during chronological aging. A new sunscreen (a bis-benzylidene campho sulfonic acid derivative) has been synthesized in our research laboratory (lambda max: 345 nm, epsilon: 47,000). Its photoprotective properties against UV-A induced damages were assessed in our mouse model. Three-month-old albino hairless mice were exposed for 1 y to suberythemal doses (35 J/sq cm) of UV-A obtained from a xenon source filtered through a WG 345 filter. One group of animals was exposed untreated, the other received a formulation containing 5% of the sunscreen prior to irradiation. At the end of the study the cutaneous properties of protected mice were compared to those of unprotected animals and to 3 and 15-month-old unirradiated controls. We found that the visible changes induced by UV-A irradiation were mainly sagging and wrinkling. Histological and electron microscopic alterations consisted of hyperkeratosis, increased density of elastic fibers with alteration of fiber orientation and increased glycosaminoglycan deposits. Biochemical changes consisted of decreases in total collagen and collagen hydroxylation and increases in both collagen III/I + III ratio and fibronectin biosynthesis. All these changes were reduced or abolished by the sunscreen.

PMID:1320278 Fourtanier A et al; Photochem Photobiol 55 (4): 549-60 (1992)


/EXPL THER/ BACKGROUND/PURPOSE: Exposure to ultraviolet (UV) radiation increases skin pigmentation and usually results in an even darkening of the skin. However, it may also occasionally lead to the development of hyperpigmented lesions due to a local overproduction of pigment. Skin pigmentation is induced both by UVB and UVA rays. METHODS: The in vivo protection by sunscreens against pigmentation was studied using the determination of a level of protection against pigmentation based on the standardized sun protection factor (SPF) test method. The method includes delayed UVB and UVA pigmentations. The level of prevention against pigmentation was determined 7 days after exposure to solar-simulated radiation by visual assessment. It was calculated using the ratio of the minimal pigmenting dose on protected skin to the minimal pigmenting dose on unprotected skin. Broadspectrum UVB/UVA filters, Mexoryl SX and Mexoryl XL, and complete formula were tested. RESULTS: Protection against pigmentation correlates with the concentration of Mexoryl SX. The levels of protection obtained show a synergetic effect of Mexoryl SX when associated with Mexoryl XL. When different products having the same SPF (same protection against erythema) and different levels of UVA protection are compared, only sunscreen products with a high level of UVA protection show a similar level of protection against sunburn and pigmentation. Products with low UVA protection have a lower capacity of preventing induced pigmentation compared with their efficacy against erythema. CONCLUSIONS: These studies have evidenced that SPF determination was not sufficient to account for the efficiency in preventing pigmentation and that UVA protection was an essential part of this prevention.

PMID:15379874 Moyal D; Photodermatol Photoimmunol Photomed 20 (5): 243-7 (2004)


For more Therapeutic Uses (Complete) data for Terephthalylidene dicamphor sulfonic acid (6 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Sunscreening Agents

Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)


5.2 Absorption, Distribution and Excretion

The potential human health risk of UV filters depends on their toxicity and the human systemic exposure which is a function of the extent of percutaneous absorption of the topically applied substance into the human organism. Using a 'mass balance' approach, a study was designed to investigate the systemically absorbed dose of [(14)C]-Mexoryl SX((R)) in humans after topical application of a typical sunscreen emulsion. In addition, to assess the correlation with in vitro experiments, the percutaneous absorption of this UVA filter through isolated human skin was measured under identical exposure conditions. When applied in vivo for a period of 4 hr, 89-94% of the applied radioactivity was recovered from the wash-off samples. In urine samples, the radioactivity slightly exceeded background levels and corresponded maximally to 0.014% of the topically applied dose. No radioactivity was measured in blood or feces sampled up to 120 hr after application. In vitro, 24 hr after a 4-hour application, [(14)C]-Mexoryl SX remained primarily on the skin surface. The mean in vitro absorption over 24 hr, adding up the amounts found in the dermis and receptor fluid, was 0.16% of the applied dose. It is concluded from the in vivo pharmacokinetic results that the systemically absorbed dose of [(14)C]-Mexoryl SX is less than 0.1%. The order of magnitude of this value correlates well with the corresponding in vitro data which overestimate the in vivo results as previously observed with other hydrophilic compounds. This study demonstrates that, under realistic exposure conditions, the human systemic exposure to this UVA filter is negligible and poses no risk to human health.

PMID:14528058 Benech-Kieffer F et al; Skin Pharmacol Appl Skin Physiol 16 (6): 343-55 (2003)


An in vivo method in humans using radioactive terephthalylidene dicamphor sulfonic acid ((14)C site not specified) showed an absorption determined up to 24 hours after a 4-hours exposure to 0.16% of the applied dose.

The Danish Environmental Protection Agency. Survey and health assessment of UV filters. p.170 (2015)


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Terephthalylidene Dicamphor Sulfonic Acid Manufacturers

A Terephthalylidene Dicamphor Sulfonic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Terephthalylidene Dicamphor Sulfonic Acid, including repackagers and relabelers. The FDA regulates Terephthalylidene Dicamphor Sulfonic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Terephthalylidene Dicamphor Sulfonic Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Terephthalylidene Dicamphor Sulfonic Acid Suppliers

A Terephthalylidene Dicamphor Sulfonic Acid supplier is an individual or a company that provides Terephthalylidene Dicamphor Sulfonic Acid active pharmaceutical ingredient (API) or Terephthalylidene Dicamphor Sulfonic Acid finished formulations upon request. The Terephthalylidene Dicamphor Sulfonic Acid suppliers may include Terephthalylidene Dicamphor Sulfonic Acid API manufacturers, exporters, distributors and traders.

click here to find a list of Terephthalylidene Dicamphor Sulfonic Acid suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Terephthalylidene Dicamphor Sulfonic Acid USDMF

A Terephthalylidene Dicamphor Sulfonic Acid DMF (Drug Master File) is a document detailing the whole manufacturing process of Terephthalylidene Dicamphor Sulfonic Acid active pharmaceutical ingredient (API) in detail. Different forms of Terephthalylidene Dicamphor Sulfonic Acid DMFs exist exist since differing nations have different regulations, such as Terephthalylidene Dicamphor Sulfonic Acid USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Terephthalylidene Dicamphor Sulfonic Acid DMF submitted to regulatory agencies in the US is known as a USDMF. Terephthalylidene Dicamphor Sulfonic Acid USDMF includes data on Terephthalylidene Dicamphor Sulfonic Acid's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Terephthalylidene Dicamphor Sulfonic Acid USDMF is kept confidential to protect the manufacturer’s intellectual property.

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Terephthalylidene Dicamphor Sulfonic Acid GMP

Terephthalylidene Dicamphor Sulfonic Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Terephthalylidene Dicamphor Sulfonic Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Terephthalylidene Dicamphor Sulfonic Acid GMP manufacturer or Terephthalylidene Dicamphor Sulfonic Acid GMP API supplier for your needs.

Terephthalylidene Dicamphor Sulfonic Acid CoA

A Terephthalylidene Dicamphor Sulfonic Acid CoA (Certificate of Analysis) is a formal document that attests to Terephthalylidene Dicamphor Sulfonic Acid's compliance with Terephthalylidene Dicamphor Sulfonic Acid specifications and serves as a tool for batch-level quality control.

Terephthalylidene Dicamphor Sulfonic Acid CoA mostly includes findings from lab analyses of a specific batch. For each Terephthalylidene Dicamphor Sulfonic Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Terephthalylidene Dicamphor Sulfonic Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (Terephthalylidene Dicamphor Sulfonic Acid EP), Terephthalylidene Dicamphor Sulfonic Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Terephthalylidene Dicamphor Sulfonic Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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