Crystal and molecular structure of silver sulphadiazine (N 1-pyrimidin-2-ylsulphanilamide)

Cook, David S.; Turner, Michael F.

doi:10.1039/p29750001021

Cited by 87 publications

(34 citation statements)

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“…The complex of a sulfa drug, sulfadiazine, with silver now appears to be one of the most effective agents for the control of infections in severely burned patients (Fox, 1968;Modak & Fox, 1973;Fox & Modak, 1974). Its crystal structure determination 0108-2701/86/111505-05501.50 (Baenziger & Struss, 1976;Cook & Turner, 1975) showed that its low solubility is due to its polymeric nature in the crystal form. A few strains of bacteria have developed resistance to silver sulfadiazine, however, so that a search has continued for additional compounds which might be effective as topical burn treatment agents.…”

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The structure of silver pefloxacin, an antibiotic related to nalidixic acid

Baenziger¹,

Fox²,

Modak³

1986

Acta Crystallogr C

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1505 l'uranium, ne d6bute qu'au-del~ de 423 K. Les 6tapes ult6rieures correspondent ~ la d6gradation de la chaine carbon6e.Cette 6volution, qui confirme l'existence de deux types de mol6cules d'eau, est en bon accord avec le spectre de diffraction X de poudre en fonction de la temp6rature qui montre que, jusque 413 K, la structure n'est pas affect~e par la d6shydratation. Au-del~t de cette temperature, le spectre subit une premi6re modification accompagnant le d~part des molecules d'eau coordin6es. L'alt~ration de la cha~ne mol6culaire qui intervient vers 483 K se traduit par la formation d'une phase amorphe. Abstract. Silver(I) 1-ethyl-6-fluoro-l,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylate tetrahydrate,Ag[C 17H~gFN303].4H20, M r = 512.31, triclinic, P1, a=8.7146 (9), b=9.8853 (11), c= 13.8115(18)A, a=69.17(1), fl=67.54(1), ),= 84.69 (1) °, V = 1026.4 (2) A 3, D x = 1.658 Mg m -3, Z =2, 2(MoKal)=0.70926,/k, B=l.01mm -~, F(000) = 524, T= 297 K, final R =0.038 for 3130 observed reflections. Two silver atoms are joined in dimeric pairs by bridging coordinating carboxyl groups from two pefloxacin molecules. The terminal piperazinyl N atom from another pefloxacin molecule also coordinates to each Ag atom. The silver coordination is completed by an O atom from a water molecule and, possibly, a bond to the other silver atom (Ag-Ag = 2.901 A). Since both ends of the pefloxacin molecules are coordinated to silver, the dimeric silver pairs are linked into a chain extending through the crystal. The general features of the structure are strikingly similar to those of silver sulfadiazine, a well known burn treatment compound. Rff~rences

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confidence: 99%

The structure of silver pefloxacin, an antibiotic related to nalidixic acid

Baenziger¹,

Fox²,

Modak³

1986

Acta Crystallogr C

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“…S-C(7) at 1.775 (4)A agrees with 1.766/i, found in sodium naphthionate tetrahydrate (Brown & Corbridge, 1966) and S-N(1) at 1.661 (3)/i, agrees with 1.666/k in y-sulphanilamide (All~aume & Decap, 1965). The other bonds in the molecule are similar to those found in other sulphanilamides and sulphadiazines, a table of comparisons is given by Cook & Turner (1975).…”

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confidence: 83%

“…This work was undertaken as part of a programme relating the crystal structures of various sulpha compounds (Cook & Turner, 1975to their therapeutic activity in the treatment of infections in burns. The material was supplied by Messrs Smith & Nephew Limited, Harlow.…”

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N1-Phenylsulphanilamide, C12H12N2O2S

Brown¹,

Cook²,

Sengier³

1984

Acta Crystallogr C

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“…Zinc sulfadiazine is used to prevent bacterial infection in burned animals and silvadene (2-sulfanilamidopyrimidine-silver(I)) is used commercially for the treatment of topical burn [15]. The crystal structures of silver sulfadiazine [16], zinc sulfadiazine [17] and cadmium sulfadiazine [18] have been reported. In our effort to contribute to metal-based drugs as alternative therapies in the management of chloroquine-resistant malaria, we have embarked on the synthesis, characterization and in vitro studies of metal complexes of antimalarial drugs [19].…”

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confidence: 99%

<b>Synthesis, characterization, antiplasmodial and antitrypanosomal activity of some metal(III) complexes of sulfadiazine</b>

Ajibade¹,

Kolawole²

2008

Bull. Chem. Soc. Eth.

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ABSTRACT. The Fe(III), Ru(III), Rh(III), and Cr(III) complexes of 4-amino-N-(2-pyrimidinyl)benzene sulfonamide (sulfadiazine) have been synthesized and characterized by elemental analysis, electronic and IR spectroscopy, conductance and room temperature magnetic susceptibility measurements. Sulfadiazine acts as a bidentate ligand through the sulfonamido and the pyrimidinic N-atoms. The compounds are non-electrolytes and the electronic spectra are consistent with the proposed octahedral geometry around the metal ions. The complexes were tested for in vitro activity against cultures of the resistant strains of Plasmodium falciparum, tripamastigotes T. b. rhodesiense and amastigotes L. donovani to determine their antiprotozoal activities. The Fe(III) complex is more active than the other complexes against the parasitic protozoa.

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Crystal and molecular structure of silver sulphadiazine (N 1-pyrimidin-2-ylsulphanilamide)

Cited by 87 publications

References 1 publication

The structure of silver pefloxacin, an antibiotic related to nalidixic acid

The structure of silver pefloxacin, an antibiotic related to nalidixic acid

N1-Phenylsulphanilamide, C12H12N2O2S

<b>Synthesis, characterization, antiplasmodial and antitrypanosomal activity of some metal(III) complexes of sulfadiazine</b>

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