Sulphadiazines

C10H10N4O2S. White powder, which darkens on exposure to light m.p. 255-256 C. Prepared by condensing p-acet-amidobenzenesulphonyl chloride with 2-aminopyrimidine and subsequent hydrolysis. Soluble sulphadiazine is the sodium salt. Sulphadiazine is the least toxic of the more potent sulphonamides. ... 

See sulphacetamide, sulphadiazine, sul-phadimidine, sulphaguanidine, sulphamera-zine, sulphamethoxypyridazine, sulphanilamide, sulphathiazole. 

Less study has been made of complexes with polydentate ligands. Ag-N linkages have been studied in relation to polynucleotide bases and the Ag-DNA interaction could be important in the use of the silver-sulphadiazine complex in burn treatment. Ethylenediamine is a bridging ligand in AgenC104 (2-coordinate silver) but essentially planar 5-coordination... 

The sulphonamides show a considerable variation in the extent of their absorption into the bloodstream. Sulphadimidine and sulphadiazine are examples of rapidly absorbed ones, whereas succinylsulphathiazone and phthalylsulphathiazole are poorly absorbed and are excreted unchanged in the faeces. 

The colorimetric assay of sulphadiazine is based on the acid-catalysed equilibrium reaction that occurs between vanillin (an aldehyde) and sulphadiazine (an aiylamine). The chemical species that forms as shown below is known as the Schiff s Base and is yellow in colour. 

Sulphadiazine Sulphathiazole Sulphamerazine Sulphamethazine Sulphamethoxazole Sulphadoxine Sulphaquinoxaline Sulphaphenazole Sulphasalazine 10-Desacetylbaccatine III Baccatine III Erythromycine... 

Major chemical contaminants implicated in food safety include pesticides, herbicides, myeotoxins and antibiotics. These analytes have been targeted by numerous groups developing SPR biosensors. As these analytes are rather small (typical molecular weight < 1,000), inhibition assay has been a preferred detection format. Examples of chemical contaminants detected by SPR biosensors include pesticides atrazine and simazine (detection limits 0.05 ng/ml and 0.1 ng/ml respectively), mycotoxin Fumonisin B1 (detection limit 50 ng/ml ), and antibiotics Sulphamethazine, Sulphadiazine (detection limits 1 ng/ml and 20 ng/ml respectively). 

Schaller, M., Korting, H. C. and Schmid, M. H., Interaction of cultured human keratinocytes with liposomes encapsulating silver sulphadiazine proof of the uptake of intact vesicles. Br. J. Dermatol, 134, 445-50, 1996. 

Benzyl penicillin 5-Fluorouracil Acebutolol Sulphadiazine Isoprenaline Prednisolone Guanethidine Pyridostigmine bromide Additional problems... 

Smith JM, Curi AL, and Pavesio CE. Crystalluria with sulphadiazine. Br J Ophthalmol 2001 85 1265-1269. 

A-heterocyclic derivatives of sulphanilamide, e.g. sulphadiazine, sul-phathiazole and sulphoxazole, have broad-spectrum antimicrobial activity. They are generally more water soluble, and thus better absorbed and retained better, i.e. excreted slowly. 

Applications of dressings soaked in aqueous silver nitrate solution have significant prophylactic action against infection in the treatment of major burns3 A salt other than the nitrate would seem to be preferable in order to avoid possible reduction to nitrite, with resulting toxicity. One such alternative is silver sulphadiazine. Because of its antibacterial action, silver nitrate is also sometimes used in eye drops. 

Dermal. Medical case histories indicate that dermal exposure to silver or silver compounds for extended periods of time can lead to local skin discoloration similar in nature to the generalized pigmentation seen after repeated oral exposure. However, the amount of silver and the duration of time required to produce this effect cannot be established with the existing information (Buckley 1963 McMahon and Bergfeld 1983). Moreover, adverse effects such as argyria have not been associated with the use of silver sulphadiazine as a bactericidal agent (Fox et al. 1969). No studies were located regarding dermal effects in animals after dermal exposure to silver or silver compounds. 

Absorption of silver nitrate across intact skin has been demonstrated in guinea pigs and is similar to that of intact human skin (Wahlberg 1965). The amount absorbed was estimated to be approximately 1 % of the applied dose within 5 hours of exposure. Silver administered in the form of silver sulphadiazine cream was minimally absorbed through both the intact and burned skin of rats and distributed throughout the body (Sano et al. 1982). The absorption of silver increased through burned skin after blister removal. The authors did not determine the percentage of the applied dose that was absorbed (Sano et al. 1982). 

Following the topical application of silver nitrate for the treatment of burns in two humans, silver was distributed to the muscles (0.03-2.3 ppm), liver (0.44 ppm), spleen (0.23 ppm), kidney (0.14 ppm), heart (0.032-0.04 ppm), and bones (0.025 ppm) (Bader 1966). No studies were located that quantitated the distribution of silver in animals following dermal exposure to silver or its compounds. However, Sano et al. (1982) detected silver in the same tissues of rats following topical application of silver sulphadiazine cream. 

Lockhart SP, Rushworth A, Azmy AAF, et al. 1983. Topical silver sulphadiazine Side effects and urinary excretion. Burns 10 9-12. 

Sano S, Fujimori R, Takashima M, et al. 1982. Absorption, excretion and tissue distribution of silver sulphadiazine. Burns 8 278-285. 

Most recently, a further study has been performed using superheated-water HPLC with NMR and MS to analyse a mixture of sulphonamides [68]. The chromatography was performed as before with D20-phosphate buffer (pD 3.0) as eluent. A temperature gradient from 160 to 200 °C at 2°C min-1 was employed. A mixture of four sulphonamides, i.e. sulacetamide, sulphadiazine, sulfamerazine and sulfamethazine, was separated in this system with UV, NMR and MS detection. It rapidly became clear from a study of the spectroscopic data that while sulfacetamide and sulfadiazine gave the expected NMR and mass spectra, those for sulfamerazine and sulfamethazine did not. These compounds gave spectra that were 3 and 6 mass units higher than expected,... 

Out of a total of 22 positive samples, 19 bile samples from the 56 that were analysed contained residues of 17ji-19Nortestosterone ranging in concentration from 8.8 /xg/1 to 125 /xg/1. These concentrations are above the action level of 2 /xg/1, but as this steroid is endogenous in the male pig it was considered that the presence of this compound was not due to illegal use. Two kidney samples contained residues of sulphadiazine (310/xg/kg and 450 /xg/kg) in excess of the MRL. One further kidney sample contained chlortetracycline (1,050 /xg/kg) in excess of the MRL. 

Figure 7.19 Ultraviolet trace (270 nm) obtained from SFC of a mixture of (A) sulphadoxine (1-SDX), (B) sulphamethazine (2-SMT), (C) sulpha-merazine (3-SMZ), (D) sulphadimethoxine (4-SDM), (E) sulphadiazine (5-SDZ), (F) sulphaquinoxaline (6-SQX), (G) sulphachlorpyridazine (7-SCP), and (H) sulphathiazole (8-STZ) on a 100 x 4.6-mm ID column packed with 5- tm amino-bonded Spherisorb. The mobile phase was initially carbon dioxide modified with 15% methanol at a flow rate of 4 ml/ min. After 4 min, the concentration of methanol was increased to 25%. Column pressure, 361 bars temperature, 90°C. [Reprinted from Ref. 33, J. Chromatogr. 540, 239 (1991) with kind permission of Elsevier Science Publishers, The Netherlands.]...

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