<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:09:14 UTC</creation_date>
  <update_date>2018-05-28 23:28:45 UTC</update_date>
  <accession>FDB010662</accession>
  <name>Sulfadiazine</name>
  <description>Antibacterial agent. It is used in some countries for control of bacterial disease in farmed fish. Not approved for aquacultural use in the USA

Sulfadiazine is a sulfonamide antibiotic.; Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of &lt;i&gt;p&lt;/i&gt;-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.</description>
  <synonyms>
    <synonym>&lt;IMG SRC="/ncidb2/images/delta.gif" WIDTH=12 HEIGHT=14&gt;zina</synonym>
    <synonym>2-(4-Aminobenzenesulfonamido)pyrimidine</synonym>
    <synonym>2-Sulfanilamido-pyrimidine</synonym>
    <synonym>2-Sulfanilamidopyridine</synonym>
    <synonym>2-Sulfanilamidopyrimidin</synonym>
    <synonym>2-Sulfanilamidopyrimidine</synonym>
    <synonym>2-Sulfanilylaminopyrimidine</synonym>
    <synonym>2-Sulfapyrimidine</synonym>
    <synonym>2-Sulphanilamidopyrimidine</synonym>
    <synonym>2-Sulphanilylaminopyrimidine</synonym>
    <synonym>4-Amino-N-(2-pyrimidinyl)benzenesulfonamide</synonym>
    <synonym>4-amino-N-(pyrimidin-2-yl)benzenesulfonamide</synonym>
    <synonym>4-Amino-N-2-pyrimidinyl- benzenesulfonamide</synonym>
    <synonym>4-Amino-N-2-pyrimidinyl-benzenesulfonamide</synonym>
    <synonym>4-Amino-N-2-pyrimidinylbenzenesulfonamide</synonym>
    <synonym>4-Amino-N-2-pyrimidinylbenzenesulfonamide, 9CI</synonym>
    <synonym>4-amino-N-2-Pyrimidinylbenzenesulphonamide</synonym>
    <synonym>4-amino-N-pyrimidin-2-ylbenzenesulfonamide</synonym>
    <synonym>Adiazin</synonym>
    <synonym>Adiazine</synonym>
    <synonym>Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-</synonym>
    <synonym>Coco-Diazine</synonym>
    <synonym>Cocodiazine</synonym>
    <synonym>Codiazine</synonym>
    <synonym>Cremodiazine</synonym>
    <synonym>Cremotres</synonym>
    <synonym>CRL-8131 &amp; Sulfadiazine</synonym>
    <synonym>Debenal</synonym>
    <synonym>Deltazina</synonym>
    <synonym>Di-azo-mul</synonym>
    <synonym>Diazin</synonym>
    <synonym>Diazolone</synonym>
    <synonym>Diazovit</synonym>
    <synonym>Eskadiazine</synonym>
    <synonym>Honey diazine</synonym>
    <synonym>Lipo-diazine</synonym>
    <synonym>Lipo-levazine</synonym>
    <synonym>Liquadiazine</synonym>
    <synonym>Metha-meridiazine</synonym>
    <synonym>Microsulfon</synonym>
    <synonym>Mixture of sulfadiazine, sulfamerazine, and sulfamethazine</synonym>
    <synonym>N'-(2-Pyrimidinyl)sulfanilamide, 8CI</synonym>
    <synonym>N(1)-2-pyrimidinylsulfanilamide</synonym>
    <synonym>N(1)-2-Pyrimidinylsulphanilamide</synonym>
    <synonym>N(1)-2-pyrimidylsulfanilamide</synonym>
    <synonym>N(1)-2-Pyrimidylsulphanilamide</synonym>
    <synonym>N(sup 1)-2-Pyrimidinylsulfanilamide</synonym>
    <synonym>N(sup1)-2-Pyrimidinylsulfanilamide</synonym>
    <synonym>N(sup1)-2-Pyrimidylsulfanilamide</synonym>
    <synonym>N1-(Pyrimidin-2-yl)sulfanilamide</synonym>
    <synonym>N1-2-Pyrimidinylsulfanilamide</synonym>
    <synonym>N1-2-Pyrimidylsulfanilamide</synonym>
    <synonym>Neazine</synonym>
    <synonym>Neotrizine</synonym>
    <synonym>Palatrize</synonym>
    <synonym>Pecta-diazine, suspension</synonym>
    <synonym>Piridisir</synonym>
    <synonym>Pirimal</synonym>
    <synonym>Pyrimal</synonym>
    <synonym>Pyrimidine, 2-sulfanilamido-</synonym>
    <synonym>Quadetts</synonym>
    <synonym>Quadramoid</synonym>
    <synonym>rBPI21 &amp; Sulfa</synonym>
    <synonym>Sanodiazine</synonym>
    <synonym>SDA</synonym>
    <synonym>Sodium sulfadiazine</synonym>
    <synonym>Solfadiazina</synonym>
    <synonym>Solfadiazina [dcit]</synonym>
    <synonym>Spofadrizine</synonym>
    <synonym>Sterazine</synonym>
    <synonym>Sulfacombin</synonym>
    <synonym>Sulfadiazene</synonym>
    <synonym>Sulfadiazin</synonym>
    <synonym>Sulfadiazina</synonym>
    <synonym>Sulfadiazine (jan/usp/inn)</synonym>
    <synonym>Sulfadiazine (TN)</synonym>
    <synonym>Sulfadiazine [usan:inn:jan]</synonym>
    <synonym>Sulfadiazinum</synonym>
    <synonym>Sulfanilamide, N(sup 1)-2-pyrimidinyl-</synonym>
    <synonym>Sulfanilamide, N1-2-pyrimidinyl-</synonym>
    <synonym>Sulfanilamide, N1-2-pyrimidinyl- (8CI)</synonym>
    <synonym>Sulfanilamide, N1-2(1H)-pyrimidinylidene-</synonym>
    <synonym>Sulfanilamidopyrimidine</synonym>
    <synonym>Sulfapirimidin</synonym>
    <synonym>Sulfapyrimidin</synonym>
    <synonym>Sulfapyrimidin (german)</synonym>
    <synonym>Sulfapyrimidine</synonym>
    <synonym>Sulfatryl</synonym>
    <synonym>Sulfazin</synonym>
    <synonym>Sulfazin (Russian pharmaceutical)</synonym>
    <synonym>Sulfazin (russian)</synonym>
    <synonym>Sulfazine</synonym>
    <synonym>Sulfolex</synonym>
    <synonym>Sulfonamide duplex</synonym>
    <synonym>Sulfonamides duplex</synonym>
    <synonym>Sulfonsol</synonym>
    <synonym>Sulfose</synonym>
    <synonym>Sulphadiazina</synonym>
    <synonym>Sulphadiazine</synonym>
    <synonym>Sulphadiazine e</synonym>
    <synonym>Sulphadiazine, BAN</synonym>
    <synonym>Sulphadiazinum</synonym>
    <synonym>Sulphapyrimidine</synonym>
    <synonym>Terfonyl</synonym>
    <synonym>Theradiazine</synonym>
    <synonym>Thi-di-mer</synonym>
    <synonym>Tri-sulfameth</synonym>
    <synonym>Trifonamide</synonym>
    <synonym>Triple sulfas</synonym>
    <synonym>Trisem</synonym>
    <synonym>Trisulfapyrimidine, oral suspension</synonym>
    <synonym>Truozine</synonym>
    <synonym>Zinc sulfadiazine</synonym>
  </synonyms>
  <chemical_formula>C10H10N4O2S</chemical_formula>
  <average_molecular_weight>250.277</average_molecular_weight>
  <monisotopic_moleculate_weight>250.052446274</monisotopic_moleculate_weight>
  <iupac_name>4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide</iupac_name>
  <traditional_iupac>sulfadiazine</traditional_iupac>
  <cas_registry_number>68-35-9</cas_registry_number>
  <smiles>NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1</smiles>
  <inchi>InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)</inchi>
  <inchikey>SEEPANYCNGTZFQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.</description>
    <direct_parent>Aminobenzenesulfonamides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzenesulfonamides</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenesulfonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonamides</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidines and pyrimidine derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminobenzenesulfonamide</substituent>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenesulfonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid amide</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Sulfonyl</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>pyrimidines</external_descriptor>
      <external_descriptor>substituted aniline</external_descriptor>
      <external_descriptor>sulfonamide</external_descriptor>
      <external_descriptor>sulfonamide antibiotic</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.01e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 255-256° dec.</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>6.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>2.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-amino-N-(pyrimidin-2-yl)benzene-1-sulfonamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>250.277</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>250.052446274</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=N1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H10N4O2S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>SEEPANYCNGTZFQ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.97</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>64.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>24.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>135547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>143281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440733</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441617</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441620</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441621</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441622</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441623</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441626</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441627</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2226621</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB14503</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>9328</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
