Salicylanilide compounds

Salicylanilide [87-17-2] - [SALICYLIC ACID AND RELATED COMPOUNDS] pol 21) - [SALICYLIC ACID AND RELATED COMPOUNDS] pol 21)... 

Other compounds under consideration include ammoniacal copper-fatty acids, isothiazolinones, benzothiazoles, sulfonamides, tetrachloroisophthalonitrile, salicylanilide derivatives, and 3-iodo-2-propynyl butylcarbamate (8-J3). 

An additional benzene ring on the acid part of the salicylanilide molecule gives rise to hydroxynaphthanilides with marked anthelmintic activity. Consequently, a number of l-hydroxy-2-naphthanilides have been prepared [38-40], of which 2 -chloro-l-hydroxy-4 -isothiocyanatonaphthanilide (24) was found to kill 100% of H. nana in rats at an oral dose of 7.5 mg/kg. The compound also showed high activity against H. diminuta in rats and Taenia spp. in dogs. Several other... 

During systematic SAR studies on salicylanilides, various compounds of type 25-26 have been prepared [42-44], of which 25 showed good activity against H. nana, while 26 was found to be effective against flukes [42-43]. 

The anthelmintic activity of various salicylanilides and related compounds (27) would suggest the following structure-activity relationship [9,11]. 

There are a number of nonspecific topical drugs, some some of which have been in use for most of this century. Early therapy of superficial mycoses utilized topical fungicides such as salicylic acid, salicylanilide, iodine tincture, and even weak fungistatic compounds such as benzoic acid. Salicylic acid is mainly a keratolytic agent that also removes the softened, loosened infected epithelial layers. In combination with benzoic acid (Whitfield s ointment), it has been a useful product for years. 

The halogenated salicylanilides (tetrachlorosalicylanilide, brominated salicylanilides) and related compounds caused an epidemic of adverse reactions to sunlight between 1960 and 1970, when they were incorporated as antibacterials in soaps and cosmetics (Wilkinson 1961 Calnan et al. 1961 Epstein et al. 1968). After 1968 a striking reduction in numbers of patients with positive photopatch tests to these compounds has been noted (Smith and Epstein 1977), and explained partly by removal from the market of the more potent photosensitizing chemicals, partly by increased awareness by physicians. 

Osmundsen (1970 b) showed a varying cross-photoreaction pattern between halogenated salicylanilides and related compounds (salicylanilide, hexachloro-phene, trichlorocarbanilide, fenticlor, Jadit, 2,4-dichlorbenzylalcohol, and zinc omadine). 

Freeman RG, Knox JM (1968) The action spectrum of photocontact dermatitis Caused by halogenated salicylanilides and related compounds. Arch Dermatol 97 130-136 Fregert S (1968) Cross sensitization among nitrofurylaminothiadazoles. Acta Derm Vene-reol (Stockh) 48 106-109... 

Smith SZ, Epstein JH (1977) Photocontact dermatitis to halogenated salicylanilides and related compounds. Arch Dermatol 113 1372-1374 Sneddon IB, Glew RC (1973) Contact dermatitis due to propanidid in an anaesthetist. Practitioner 211 321-323... 

Recently, the modified broadening index, detection index, densitometric visualizing index (DVl), and modified contrast index were used for the evaluation of detectabihty effects of salicylanilide, estradiol, and ibu-profen. Estradiol is a steroid compound, but it contains an aromatic ring with hydroxyl group about phenohc character. Salicylanilide was detected on glass plates precoated with a 0.50 mm layer of sihca gel 6OF254 (E. Merck, 1.05744) and with a 0.25 mm layer of silica gel 6OF254 (E. Merck, 1.05715), as well as on aluminum plates precoated with a 0.20 mm... 

Also salicylanilides (2-hydroxybenzanilides), long chain A-alkyl-salicylamides and carbanilides (urea derivatives) belong to the amide compounds with antimicrobial action. They are membrane-active substances, i.e. very small concentrations suffice to achieve microbistatic effects whereas microbicidal effects call for much higher addition rates. 

Salicylanilide is especially active against fungi. As it is a practically odourless compound which does not cause coloration and is not hazardous in application, it has been used for the protection of textiles, leather, paper, plastic, paints, adhesives, etc. However, the compound is susceptible to leaching and therefore does not perform satisfactorily on material exposed outdoors. Effective addition rates are high, e.g. up to 10% in paints. Salicylanilide therefore has been widely substituted by more active and more economic microbicides. The sodium salt of salicylanilide may be used in fungicidal wall washes. 

Fasciolicidal action was also reported for another series of salicylanilides in which an electronegative substituent was introduced in the 3-position. The choice of substituents in the aniline ring was restricted to halogens, methyl groups and tri-halogenated methyls (which improve lipid solubility). The most effective compounds were 3-nitro-2,6-dihydroxybenzoic acid anilides. 

Cosmetic manufacturers may use essentially any raw material as a cosmetic ingredient insofar as it is not considered as only a drug active ingredient, and market the product without approval. The law regulates only colour additives specifically approved for cosmetics and a few prohibited and restricted ingredients (e.g. bithionol, mercury compounds, vinyl chloride, halogenated salicylanilides). Cosmetics should not be contaminated with nitrosamines, 1,4-dioxane and pesticide residues, whose potential presence is regularly checked by the FDA (see Section 2.1). 

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