Anilides toxicity

Lldoc ine. Lidocaine hydrochloride, an anilide, was originally introduced as a local anesthetic in 1943 and found to be a potent antiarrhythmic in 1960. The compound is a reverse amide of procainamide. Lidocaine is generally considered to be the dmg of choice in the treatment of ventricular arrhythmias and those originating from digitalis glycoside toxicity (1,2,15—17). 

Starmer GA, McLean S, Thomas J. 1971. Analgesic potency and acute toxicity of substituted anilides and benzamides. Toxicol Appl Pharmacol 19 20-28. 

Relative to the fate in humans of the l pes of compounds just discu.s.sed. Brudie and Axelrod " " point out that acet-anilid and phenacetin are metabolized by two different routes. Acctaniiid is metabolized primarily to Af-acetyl-p-aminophenol and acetaminophen and only a small amount to aniline, which they showed to be the precursor of phenyl-hydroxylamine. the compound re.sponsible for methcmoglobin formation. Phenacetin is mostly dccthylated to acetaminophen. whereas a small amount is convened by dcacctylation top-phenetidinc. also responsible for methemoglobin formation. With both acetanilid and phenacetin. the metabolite acetaminophen is believed to be responsible for the analgesic activity. Because of the toxicity described above, both are no longer available, replaced primarily by acetaminophen. 

Study was (N-2 (carboxyethyl)-2-(3 -nitro-l -triazolyl)acetamide, the carboxylic acid derivative of sanazole, which possesses an optimal combination of desired properties such as selective toxicity for hypoxic cells and lowered lipophilicity, resulting in lowered neurotoxicity. The BFCA used was l,4,7,10-tetraaza-l-(4 -aminobenzylacetamido)-cyclododecane-4,7,10-triacetic acid (p-amino-DOTA-anilide), a DOTA derivative. Radiolabelling of the sanazole-BFCA conjugate (Fig. 8.18) with Lu was achieved under optimized conditions, yielding complexation of approximately 98%. 

Several potential etiologies were investigated, including infectious agents, pet-borne vectors, contaminated food, organophosphate pesticide exposure, and vinyl chloride contamination from food containers, before a link was made between the new disease and the consumption of adulterated cooking oil. Chemical analysis of the case-associated oil identified brassicasterol, a marker for rapeseed oil, trace amounts of aniline, oleyl anilide, and other fatty acid anilides and contaminants (Aldridge, 1992 Posada de la Paz et al., 1996 Ruiz-Mendez et al., 2001). The toxin or toxins appear to be stable in oil, since consumption of toxic oil one year after the main epidemic led to development of the disease. 

To evaluate the role of specific aniline derivatives in the induction of an autoimmune response, animals were exposed to purified anilides and PAP esters. Oleyl and linoleyl anilides were found to be toxic to the rat lung (Tena, 1982), and anilides induced elevated IgE levels and T cells in mice (Lahoz et al., 1997). Neither PAP nor its monoester induced overt toxicity in Lewis and LAC rats or MF1 mice, but PAP induced mesenteric and pulmonary thromboembolism in rats (Gelpi et al., 2002). Most anilides possess... 

Bell SA, Sander C, Kuntze I, Chatelain R (1999) The acute pathology of fatty acid anilides and linoleic diester of 3-phenylamino-1,2-propanediol in mice possible implication as aetiologic agents for the toxic oil syndrome. Arch Toxicol, 73 493-495. 

Bell SA, Kuntze I, Caputo A, Chatelain R (2002) Strain-dependent in vitro and in vivo effects of oleic acid anilides on splenocytes and T cells in a murine model of the toxic oil syndrome. Food Chem Toxicol, 40 19-24. 

Berking C, Hobbs MV, Chatelain R, Meurer M, Bell SA (1998) Strain-dependent cytokine profile and susceptibility to oleic acid anilide in a murine model of the toxic oil syndrome. Toxicol Appl Pharmacol, 148 222-228. 

Tena G (1982) Fatty acid anilides and the toxic oil syndrome. Lancet, 1(8263) 98. 

Beilstein Handbook Reference) Apache BAS-3170 BAS 3170F Benefit Benodanil Benzamide, 2-iodo-N-phenyl- Benzanilide, 2-iodo- BRN 2725018 Calirus 2-lodo-N-phenylbenzamide 2-lodobenzanilide 2-lodobenzoic add anilide NSC 100499. Systemic and contxt fungicide with protective and curative xtion. Used for control of rust disease in various crops. Colorless crystals mp = 137" soluble in H2O (0.002 g/100 ml), MezCO (40 g/100 ml), EtOAc (12 g/100 ml), EtOH (9.3 g/100 ml), CHCI3 (7.7 g/100 ml) LD50 (rat, gpg orl) > 6400 mg/kg, (rat der) > 2000 mg/kg LCsO (trout 96 hr.) = 6.4 mg/l non-toxic to bees. BASF... 

These toxic components of the coatings can be copper oxides (I), mercury, tin-bis(tributyl)oxide, barium metaborate, anilide of salicylic acid, phenols and their derivatives, compounds of aminoformic acids, etc. [87]. In the area of metal ion toxins copper protoxide, lead and tin derivatives have recently come into extensive use. 

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