Ecamsule

562.7

562.69

410-960-6

Solid

159.64000

1.35

1.4±0.1 g/cm3

255° (dec)

1.631

In water, 0.1507 mg/L at 25 °C (est)

Precautions for safe handling: Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.

6.28X10-23 mm Hg at 25 °C (est)

Henry's Law constant = 2.07X10-23 atm-cu m/mol at 25 °C (est)

pKa = 1.99 /sulfuric acid moiety/

NONH for all modes of transport

1

41

26-39

Xi

Stable under recommended storage conditions.

P280-P305 + P351 + P338 + P310

H318

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Oxidizing agents.

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed over-the-counter drug products, including ecamsule, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

|Danger|H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]|P280, P305+P351+P338, and P310|H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]|Aggregated GHS information provided by 3 companies from 1 notifications to the ECHA C&L Inventory.

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.|Precautions for safe handling: Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

IDENTIFICATION AND USE: Terephthalylidene dicamphor sulfonic acid is a solid. It is used as broad spectrum UVA absorber with some UVB absorption. It has been tested as an ultraviolet screen in animals. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: In a 90-day oral repeat dose study in rats, no dose related effects were found at 300 mg/kg/day. At 1,000 mg/kg/day there was phosphoremia in males at week 4 and decreased protein, albumin and globulin levels in females at week 13. There was some evidence of variation in thyroid weight in the male animals fed terephthalylidene dicamphor sulfonic acid, however, there was some doubt as to validity of this observation as the control animals were found to have unusually low thyroid weights. Follow up 21-day studies using the triethalanoamine and sodium salts on thyroid metabolism found no treatment related changes at dose rates of 305 mg/kg and 444 mg/kg respectively.

LD50 Rat oral >1,835 mg/kg|LD50 Rat dermal >1,637 mg/kg

Terephthalylidene dicamphor sulfonic acid's (Ecamsule) production and use as a ultraviolet screen(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.4X10+5(SRC), determined from a structure estimation method(2), indicates that terephthalylidene dicamphor sulfonic acid is expected to be immobile in soil(SRC). A pKa of 1.99 for the sulfuric acid moiety(3) suggests that this compound will exist entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Terephthalylidene dicamphor sulfonic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-23 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2018).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.4X10+5(SRC), determined from a structure estimation method(2), indicates that terephthalylidene dicamphor sulfonic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 1.99 for the sulfuric acid moiety(4) suggests terephthalylidene dicamphor sulfonic acid will exist almost in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 3.83(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2018).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), terephthalylidene dicamphor sulfonic acid, which has an estimated vapor pressure of 6.3X10-23 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase terephthalylidene dicamphor sulfonic acid may be removed from the air by wet and dry deposition(SRC). Terephthalylidene dicamphor sulfonic acid absorbs UV light at wavelength 345 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Terephthalylidene dicamphor sulfonic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Terephthalylidene dicamphor sulfonic acid absorbs UV light at wavelength 345 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for terephthalylidene dicamphor sulfonic acid(SRC), using an estimated log Kow of 3.83(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of terephthalylidene dicamphor sulfonic acid can be estimated to be 2.4X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that terephthalylidene dicamphor sulfonic acid is expected to be immobile in soil(SRC). A pKa of 1.99 for the sulfuric acid moiety(3) suggests that this compound will exist entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

A pKa of 1.99 for the sulfuric acid moiety(1) indicates terephthalylidene dicamphor sulfonic acid will exist entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Terephthalylidene dicamphor sulfonic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-23 mm Hg(SRC), determined from a fragment constant method(2).

Occupational exposure to terephthalylidene dicamphor sulfonic acid may occur through inhalation and dermal contact with this compound at workplaces where terephthalylidene dicamphor sulfonic acid is produced or used. Limited use data indicate that the general population may be exposed to terephthalylidene dicamphor sulfonic acid via dermal contact with a limited number of sunscreen products containing terephthalylidene dicamphor sulfonic acid. (SRC)

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

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.)

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.|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.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

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

When used in OTC sunscreen drug products in the United States, this ingredient must be called ecamsule. For cosmetics and personal care products in the United States, terephthalylidene dicamphor sulfonic acid may be used as an ultraviolet light absorber. In this case, the ingredient protects the product from deterioration by absorbing UV light. When used to protect the product, this ingredient is called terephthalylidene dicamphor sulfonic acid.

Sixteen UV filters were simultaneously analyzed using the high-performance liquid chromatographic method. They were drometrizole (USAN Drometrizole), 4-methylbenzylidene camphor (USAN Enzacamene), menthyl anthranilate (USAN Menthyl anthranilate), benzophenone-3 (USAN Oxybenzone), benzophenone-8 (USAN Dioxybenzone), butyl methoxydibenzoylmethane (USAN Avobenzone), ethylhexyl triazone (USAN Octyl triazone), octocrylene (USAN Octocrylene), ethylhexyl dimethyl p-aminobenzoic acid (USAN Padimate O), ethylhexyl methoxycinnamate (USAN Octinoxate), p-aminobenzoic acid (USAN Aminobenzoic acid), 2-phenylbenzimidazole-5-sulfonic acid (USAN Ensulizole), isoamyl p-methoxycinnamate (USAN Amiloxate), and recent UV filters such as diethylhexyl butamidotriazone (USAN Iscotrizinol), methylene bis-benzotriazolyl tetramethylbutylphenol (USAN Bisoctrizole), and terephthalylidene dicamphor sulfonic acid (USAN Ecamsule). Separation of the UV filters was carried out in a C(18) column with a gradient of methanol-phosphate buffer, and the UV detection was at 300, 320, or 360 nm without any interference. The limits of detection were between 0.08 and 1.94 ug/mL, and the limits of quantitation were between 0.24 and 5.89 ug/mL. The extracting solvent for the UV filters was methanol, except for ethylhexyl triazone and methylene bis-benzotriazolyl tetramethylbutylphenol, which were prepared with tetrahydrofuran. The recoveries from spiked samples were between 94.90% and 116.54%, depending on the matrixes used. The developed method was applied to 23 sunscreens obtained from local markets, and the results were acceptable to their own criteria and to maximum authorized concentrations. Consequently, these results would provide a simple extracting method and a simultaneous determination for various UV filters, which can improve the quality control process as well as the environmental monitoring of sunscreens.|Liquid chromatography was used for the determination of the three most used water-soluble UV filters, benzophenone-4 (BZ4), terephthalylidene dicamphor sulfonic acid (TDS), and phenylbenzimidazole sulfonic acid (PBS), in aqueous sunscreen sprays. A C18 stationary phase and an isocratic mobile phase of EtOH-20 mM sodium acetate buffer of pH 4.6 (30:70, v/v) were used at a flow-rate of 0.5 mL/min. Mobile phase was also used as solvent for samples and standards. UV detection was at 313 nm. The analytical run took 5.5 min. The limits of detection were 0.5, 0.9 and 2 ug/mL for BZ4, TDS and PBS, respectively. The proposed method does not involve highly toxic solvents.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Cosmetics -> Uv absorber; Uv filter