<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 01:52:13 UTC</creation_date>
  <update_date>2025-11-19 02:57:05 UTC</update_date>
  <accession>FDB029229</accession>
  <name>Isoniazid</name>
  <description>Isoniazid (also called isonicotinyl hydrazine or INH; sold as Laniazid, Nydrazid) is an organic compound that is the first-line antituberculosis medication in prevention and treatment. First discovered in 1912 as an inhibitor of the MAO enzyme, it was first used as an antidepressant, but discontinued due to side effects. In 1951, it was later discovered that isoniazid was effective against TB. Isoniazid is never used on its own to treat active tuberculosis because resistance quickly develops.; Isoniazid is a bactericidal agent active against organisms of the genus Mycobacterium, specifically &lt;i&gt;M. tuberculosis&lt;/i&gt;, &lt;i&gt;M. bovis&lt;/i&gt; and &lt;i&gt;M. kansasii&lt;/i&gt;. It is a highly specific agent, ineffective against other microorganisms. Isoniazid is bactericidal to rapidly-dividing mycobacteria, but is bacteriostatic if the mycobacterium is slow-growing.; Isoniazid is a prodrug and must be activated by bacterial catalase. It is activated by catalase-peroxidase enzyme KatG which couples the isonicotinic acyl with NADH to form isonicotinic acyl-NADH complex. This complex binds tightly to ketoenoylreductase known as InhA, thereby blocking the natural enoyl-AcpM substrate and the action of fatty acid synthase. This process inhibits the synthesis of mycolic acid required for the mycobacterial cell wall. A range of radicals are produced by KatG activation of Isoniazid, including nitric oxide, that has also been shown to be important in the action of another antimycobacterial prodrug PA824. [HMDB]</description>
  <synonyms>
    <synonym>(HBD) Human beta-defensin-1 &amp; INH</synonym>
    <synonym>4-(Hydrazinocarbonyl)pyridine</synonym>
    <synonym>4-Pyridinecarbonylhydrazine</synonym>
    <synonym>4-Pyridinecarboxylic acid hydrazide</synonym>
    <synonym>4-Pyridinecarboxylic acid, hydrazide</synonym>
    <synonym>4-Pyridinecarboxylic hydrazide</synonym>
    <synonym>4-Pyridylcarbonyl hydrazide</synonym>
    <synonym>4-Pyridylcarbonylhydrazide</synonym>
    <synonym>Abdizide</synonym>
    <synonym>Amidon</synonym>
    <synonym>Andrazide</synonym>
    <synonym>Anidrasona</synonym>
    <synonym>Antimicina</synonym>
    <synonym>Antituberkulosum</synonym>
    <synonym>Armacide</synonym>
    <synonym>Armazid</synonym>
    <synonym>Armazide</synonym>
    <synonym>Atcotibine</synonym>
    <synonym>Azt + isoniazid</synonym>
    <synonym>Azuren</synonym>
    <synonym>Bacillen</synonym>
    <synonym>Bacillin</synonym>
    <synonym>Cedin</synonym>
    <synonym>Cedin (aerosol)</synonym>
    <synonym>Cemidon</synonym>
    <synonym>Chemiazid</synonym>
    <synonym>Chemidon</synonym>
    <synonym>Continazine</synonym>
    <synonym>Cortinazine</synonym>
    <synonym>Cotinazin</synonym>
    <synonym>Cotinizin</synonym>
    <synonym>Defonin</synonym>
    <synonym>Dibutin</synonym>
    <synonym>Diforin</synonym>
    <synonym>Dinacrin</synonym>
    <synonym>Ditubin</synonym>
    <synonym>Dom-Isoniazid 300mg Tablets</synonym>
    <synonym>Dow-isoniazid</synonym>
    <synonym>Ebidene</synonym>
    <synonym>Eralon</synonym>
    <synonym>Ertuban</synonym>
    <synonym>Eutizon</synonym>
    <synonym>Evalon</synonym>
    <synonym>Fetefu</synonym>
    <synonym>Fimalene</synonym>
    <synonym>FRS-3</synonym>
    <synonym>FSR 3</synonym>
    <synonym>FSR-3</synonym>
    <synonym>Ftivazide</synonym>
    <synonym>GINK</synonym>
    <synonym>HIA</synonym>
    <synonym>Hid rasonil</synonym>
    <synonym>Hidranizil</synonym>
    <synonym>Hidrasonil</synonym>
    <synonym>Hidrulta</synonym>
    <synonym>Hidrun</synonym>
    <synonym>Hycozid</synonym>
    <synonym>Hydra</synonym>
    <synonym>Hydrazid</synonym>
    <synonym>Hydrazide</synonym>
    <synonym>Hydrazide, isonicotinic acid</synonym>
    <synonym>Hyozid</synonym>
    <synonym>Hyzyd</synonym>
    <synonym>I.a.I</synonym>
    <synonym>I.a.I.</synonym>
    <synonym>I3377_FLUKA</synonym>
    <synonym>I3377_SIGMA</synonym>
    <synonym>Ido-tebin</synonym>
    <synonym>Idrazide dell'acido isonicotinico [italian]</synonym>
    <synonym>Idrazil</synonym>
    <synonym>INAH</synonym>
    <synonym>INH</synonym>
    <synonym>Inh-burgthal</synonym>
    <synonym>INHd20</synonym>
    <synonym>Inizid</synonym>
    <synonym>Iscotin</synonym>
    <synonym>Isidrina</synonym>
    <synonym>Ismazide</synonym>
    <synonym>Isobicina</synonym>
    <synonym>Isocid</synonym>
    <synonym>Isocidene</synonym>
    <synonym>Isoco tin</synonym>
    <synonym>Isocotin</synonym>
    <synonym>Isohydrazide</synonym>
    <synonym>Isokin</synonym>
    <synonym>Isolyn</synonym>
    <synonym>Isonerit</synonym>
    <synonym>Isonex</synonym>
    <synonym>Isoniacid</synonym>
    <synonym>Isoniazid (JP15/USP/INN)</synonym>
    <synonym>Isoniazid [ban:inn:jan]</synonym>
    <synonym>Isoniazid [inn:ban:jan]</synonym>
    <synonym>Isoniazid &amp; CRL8131</synonym>
    <synonym>Isoniazid &amp; eep</synonym>
    <synonym>Isoniazid &amp; propolis</synonym>
    <synonym>Isoniazid daily for 9 months</synonym>
    <synonym>Isoniazid sa</synonym>
    <synonym>Isoniazid(isonicotinic acid)</synonym>
    <synonym>Isoniazida [inn-spanish]</synonym>
    <synonym>Isoniazide</synonym>
    <synonym>Isoniazidum [inn-latin]</synonym>
    <synonym>Isonicazide</synonym>
    <synonym>Isonicid</synonym>
    <synonym>Isonico</synonym>
    <synonym>Isonicotan</synonym>
    <synonym>Isonicotil</synonym>
    <synonym>Isonicotinate hydrazide</synonym>
    <synonym>Isonicotinhydrazid</synonym>
    <synonym>Isonicotinic acid hydrazide</synonym>
    <synonym>Isonicotinic hydrazide</synonym>
    <synonym>Isonicotinohydrazide</synonym>
    <synonym>isonicotinohydrazide (ACD/Name 4.0)</synonym>
    <synonym>Isonicotinoyl hydrazide</synonym>
    <synonym>Isonicotinoylhydrazide</synonym>
    <synonym>Isonicotinoylhydrazine</synonym>
    <synonym>Isonicotinsaeurehydrazid [german]</synonym>
    <synonym>Isonicotinyl hydrazide</synonym>
    <synonym>Isonicotinyl hydrazine</synonym>
    <synonym>Isonicotinylhydrazide</synonym>
    <synonym>Isonicotinylhydrazine</synonym>
    <synonym>Isonide</synonym>
    <synonym>Isonidrin</synonym>
    <synonym>Isonikazid</synonym>
    <synonym>Isonilex</synonym>
    <synonym>Isonin</synonym>
    <synonym>Isonindon</synonym>
    <synonym>Isonirit</synonym>
    <synonym>Isoniton</synonym>
    <synonym>Isonizida</synonym>
    <synonym>Isonizide</synonym>
    <synonym>Isopyrin</synonym>
    <synonym>Isotamine</synonym>
    <synonym>Isotamine powder</synonym>
    <synonym>Isotamine Syr Pediatric 50mg/5ml</synonym>
    <synonym>Isotamine-100</synonym>
    <synonym>Isotamine-300</synonym>
    <synonym>Isotebe</synonym>
    <synonym>Isotebezid</synonym>
    <synonym>Isotinyl</synonym>
    <synonym>Isozid</synonym>
    <synonym>Isozid e</synonym>
    <synonym>Isozide</synonym>
    <synonym>Isozyd</synonym>
    <synonym>ISZ</synonym>
    <synonym>Laniazid</synonym>
    <synonym>Laniazid (TN)</synonym>
    <synonym>Laniozid</synonym>
    <synonym>Lanizid</synonym>
    <synonym>Mixture name</synonym>
    <synonym>Mybasan</synonym>
    <synonym>nchembio884-comp3</synonym>
    <synonym>Neo-tizide</synonym>
    <synonym>Neoteben</synonym>
    <synonym>Neoxin</synonym>
    <synonym>Neumandin</synonym>
    <synonym>Nevin</synonym>
    <synonym>Niadrin</synonym>
    <synonym>Niazid</synonym>
    <synonym>Nicazide</synonym>
    <synonym>Nicetal</synonym>
    <synonym>Nicizina</synonym>
    <synonym>Niconyl</synonym>
    <synonym>Nicotibina</synonym>
    <synonym>Nicotibine</synonym>
    <synonym>Nicotisan</synonym>
    <synonym>Nicozide</synonym>
    <synonym>Nidaton</synonym>
    <synonym>Nidra zid</synonym>
    <synonym>Nidrazid</synonym>
    <synonym>Nikozid</synonym>
    <synonym>Niplen</synonym>
    <synonym>Nitadon</synonym>
    <synonym>Niteban</synonym>
    <synonym>Nitebannsc 9659</synonym>
    <synonym>Nydrazid</synonym>
    <synonym>Nyscozid</synonym>
    <synonym>Pelazid</synonym>
    <synonym>Percin</synonym>
    <synonym>Phthisen</synonym>
    <synonym>Phthivazide</synonym>
    <synonym>Pms-Isoniazid 100mg/Tab</synonym>
    <synonym>Pms-Isoniazid 300mg/Tab</synonym>
    <synonym>Pms-Isoniazid Syrup 50mg/5ml</synonym>
    <synonym>Pms-Isoniazid Tab 50mg</synonym>
    <synonym>Preparation 6424</synonym>
    <synonym>Prestwick_578</synonym>
    <synonym>Pycazide</synonym>
    <synonym>Pyreazid</synonym>
    <synonym>Pyricidin</synonym>
    <synonym>Pyridicin</synonym>
    <synonym>pyridine-4-carbohydrazide</synonym>
    <synonym>Pyrizidin</synonym>
    <synonym>Raumanon</synonym>
    <synonym>Razide</synonym>
    <synonym>Retozide</synonym>
    <synonym>Rifamate</synonym>
    <synonym>Rifater</synonym>
    <synonym>Rimicid</synonym>
    <synonym>Rimif on</synonym>
    <synonym>Rimifon</synonym>
    <synonym>Rimiphone</synonym>
    <synonym>Rimitsid</synonym>
    <synonym>Robiselin</synonym>
    <synonym>Robisellin</synonym>
    <synonym>Roxifen</synonym>
    <synonym>Ru-ef-TB</synonym>
    <synonym>RY-ef-TB</synonym>
    <synonym>Sanohidrazina</synonym>
    <synonym>Sauterazid</synonym>
    <synonym>Sauterzid</synonym>
    <synonym>Stanozide</synonym>
    <synonym>TB-phlogin</synonym>
    <synonym>TB-razide</synonym>
    <synonym>TB-vis</synonym>
    <synonym>Tebecid</synonym>
    <synonym>Tebemid</synonym>
    <synonym>Tebenic</synonym>
    <synonym>Tebexin</synonym>
    <synonym>Tebilon</synonym>
    <synonym>Tebos</synonym>
    <synonym>Teebaconin</synonym>
    <synonym>Tekazin</synonym>
    <synonym>Tibazide</synonym>
    <synonym>Tibemid</synonym>
    <synonym>Tibiazide</synonym>
    <synonym>Tibison</synonym>
    <synonym>Tibivis</synonym>
    <synonym>Tibusan</synonym>
    <synonym>Tubazid</synonym>
    <synonym>Tubazide</synonym>
    <synonym>Tubeco</synonym>
    <synonym>Tubecotubercid</synonym>
    <synonym>Tubercid</synonym>
    <synonym>Tuberian</synonym>
    <synonym>Tubicon</synonym>
    <synonym>Tubilysin</synonym>
    <synonym>Tubizid</synonym>
    <synonym>Tubomel</synonym>
    <synonym>Tyvid</synonym>
    <synonym>Unicocyde</synonym>
    <synonym>Unicozyde</synonym>
    <synonym>Usaf cb-2</synonym>
    <synonym>Vazadrine</synonym>
    <synonym>Vederon</synonym>
    <synonym>WLN: T6NJ DVMZ</synonym>
    <synonym>Zidafimia</synonym>
    <synonym>Zinadon</synonym>
    <synonym>Zonazide</synonym>
  </synonyms>
  <chemical_formula>C6H7N3O</chemical_formula>
  <average_molecular_weight>137.1393</average_molecular_weight>
  <monisotopic_moleculate_weight>137.058911861</monisotopic_moleculate_weight>
  <iupac_name>pyridine-4-carbohydrazide</iupac_name>
  <traditional_iupac>isoniazid</traditional_iupac>
  <cas_registry_number>54-85-3</cas_registry_number>
  <smiles>NNC(=O)C1=CC=NC=C1</smiles>
  <inchi>InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)</inchi>
  <inchikey>QRXWMOHMRWLFEY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.</description>
    <direct_parent>Pyridinecarboxylic acids and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acid hydrazides</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid hydrazide</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carbohydrazide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.49e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-0.69</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>13.61</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>3.35</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>pyridine-4-carbohydrazide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>137.1393</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>137.058911861</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NNC(=O)C1=CC=NC=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H7N3O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>QRXWMOHMRWLFEY-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>68.01</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>37.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>3171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>103097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>161833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
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  <chebi_id>6030</chebi_id>
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  <fbonto_id/>
  <foodb_id/>
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  <foods>
  </foods>
  <flavors>
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  <enzymes>
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  <health_effects>
  </health_effects>
</compound>
