<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3110</id>
  <title>T3D3068</title>
  <common-name>Silver sulfadiazine</common-name>
  <description>Silver sulfadiazine is only found in individuals that have used or taken this drug. It is a sulfa derivative topical antibacterial used primarily on second- and third-degree burns. [Wikipedia] Studies utilizing radioactive micronized silver sulfadiazine, electron microscopy, and biochemical techniques have revealed that the mechanism of action of silver sulfadiazine on bacteria differs from silver nitrate and sodium sulfadiazine. Silver sulfadiazine acts only on the cell membrane and cell wall to produce its bactericidal effect. A specific mechanism of action has not been determined, but silver sulfadiazine's effectiveness may possibly be from a synergistic interaction, or the action of each component. Silver is a biocide, which binds to a broad range of targets. Silver ions bind to nucleophilic amino acids, as well as sulfhydryl, amino, imidazole, phosphate, and carboxyl groups in proteins, causing protein denaturation and enzyme inhibition. Silver binds to surface membranes and proteins, causing proton leaks in the membrane, leading to cell death. Sulfadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.</description>
  <cas>22199-08-2</cas>
  <pubchem-id>441244</pubchem-id>
  <chemical-formula>C10H9AgN4O2S</chemical-formula>
  <weight>355.949710</weight>
  <appearance>White powder.</appearance>
  <melting-point>285°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>7.87e+00 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Very limited penetration through the skin. Only when applied to very large area burns is absorption into the body generally an issue.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Studies utilizing radioactive micronized silver sulfadiazine, electron microscopy, and biochemical techniques have revealed that the mechanism of action of silver sulfadiazine on bacteria differs from silver nitrate and sodium sulfadiazine. Silver sulfadiazine acts only on the cell membrane and cell wall to produce its bactericidal effect. A specific mechanism of action has not been determined, but silver sulfadiazine's effectiveness may possibly be from a synergistic interaction, or the action of each component. Silver is a biocide, which binds to a broad range of targets. Silver ions bind to nucleophilic amino acids, as well as sulfhydryl, amino, imidazole, phosphate, and carboxyl groups in proteins, causing protein denaturation and enzyme inhibition. Silver binds to surface membranes and proteins, causing proton leaks in the membrane, leading to cell death. Sulfadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.</mechanism-of-toxicity>
  <metabolism>The degradation of sulfonamides has two different pathways: the N-acetylation pathway which is genetically determined and saturable, and the cytochrome P450 pathway which produces toxic hydroxylamine metabolites "detoxified" by glutathione. (A2885)</metabolism>
  <toxicity>LD50: 10001 mg/kg (oral, rat)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Indicated as an adjunct for the prevention and treatment of wound sepsis in patients with second- and third-degree burns.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Health effects include areas of dead skin, red and raised rash on the body, and argyria (Skin discoloration). [Wikipedia]</health-effects>
  <symptoms>Symptoms include burning sensation. [Wikipedia]</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:29:00Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:56Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Silver_sulfadiazine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>9142</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Silver sulfadiazine</stitch-id>
  <drugbank-id>DB05245</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins>CYP2C9 (P11712) Arylamine N-Acetyltransferase 2 (P11245)</metabolizing-proteins>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[Ag+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C1=NC=CC=N1</moldb-smiles>
  <moldb-formula>C10H9AgN4O2S</moldb-formula>
  <moldb-inchi>InChI=1S/C10H9N4O2S.Ag/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h1-7H,11H2;/q-1;+1</moldb-inchi>
  <moldb-inchikey>InChIKey=UEJSSZHHYBHCEL-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">357.137</moldb-average-mass>
  <moldb-mono-mass type="decimal">355.949714262</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB15610</hmdb-id>
  <chembl-id>CHEMBL1382627</chembl-id>
  <chemspider-id>390017</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Charles L. Fox, Jr., Shanta M. Modak, Paul Fox, &amp;#8220;Wound dressing comprising silver sulfadiazine incorporated in animal tissue and method of preparation.&amp;#8221; U.S. Patent US4599226, issued September, 1977.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
