<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:21 UTC</creation_date>
  <update_date>2025-11-18 22:37:07 UTC</update_date>
  <accession>FDB002390</accession>
  <name>Oxytetracycline</name>
  <description>Clinically used broad-spectrum antibacterial antibiotic. Approved by FDA for use in fish and animal feeds

Oxytetracycline is known as a broad-spectrum antibiotic due to its activity against such a wide range of infections. It was the second of the tetracyclines to be discovered. Oxytetracycline, like other tetracyclines, is used to treat many infections common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne, but alternatives sould be sought if no improvement occurs by 3 months.</description>
  <synonyms>
    <synonym>2058-46-0 (mono-hydrochloride)</synonym>
    <synonym>5-Hydroxy-tetracycline</synonym>
    <synonym>5-Hydroxytetracycline</synonym>
    <synonym>6153-64-6 (di-hydrate)</synonym>
    <synonym>6153-65-7 (di-hydrochloride salt, di-hydrate)</synonym>
    <synonym>7179-50-2 (calcium (1:1) salt)</synonym>
    <synonym>79-57-2 (ANHYDROUS)</synonym>
    <synonym>Abbocin</synonym>
    <synonym>Adamycin</synonym>
    <synonym>Antibiotic TM 25</synonym>
    <synonym>Berkmycen</synonym>
    <synonym>Biostat</synonym>
    <synonym>Biostat pa</synonym>
    <synonym>Bisolvomycin</synonym>
    <synonym>Clinimycin</synonym>
    <synonym>Clinimycin?</synonym>
    <synonym>Dabicycline</synonym>
    <synonym>Dalimycin</synonym>
    <synonym>Fanterrin</synonym>
    <synonym>Galsenomycin</synonym>
    <synonym>Geomycin</synonym>
    <synonym>Geomycin (streptomyces vimosus)</synonym>
    <synonym>Geomycin?</synonym>
    <synonym>Geotilin</synonym>
    <synonym>Hydroxytetracycline</synonym>
    <synonym>Imperacin</synonym>
    <synonym>Lenocycline</synonym>
    <synonym>Liquamycin</synonym>
    <synonym>Liquamycin LA 200</synonym>
    <synonym>Macocyn</synonym>
    <synonym>Medamycin</synonym>
    <synonym>Mycoshield TMQTHC 20</synonym>
    <synonym>NSC 9169</synonym>
    <synonym>NSC9169 (HCL)</synonym>
    <synonym>Oksisyklin</synonym>
    <synonym>Ossitetraciclina</synonym>
    <synonym>Ossitetraciclina [dcit]</synonym>
    <synonym>OTC</synonym>
    <synonym>Otc (antibiotic)</synonym>
    <synonym>Oxacycline</synonym>
    <synonym>Oxitetraciclina</synonym>
    <synonym>Oxitetracyclin</synonym>
    <synonym>Oxitetracyclinum</synonym>
    <synonym>Oxy-kesso-tetra</synonym>
    <synonym>Oxydon</synonym>
    <synonym>Oxymycin</synonym>
    <synonym>Oxymykoin</synonym>
    <synonym>Oxypam</synonym>
    <synonym>Oxysteclin</synonym>
    <synonym>Oxyterracin</synonym>
    <synonym>Oxyterracine</synonym>
    <synonym>Oxyterracyne</synonym>
    <synonym>Oxytetracid</synonym>
    <synonym>Oxytetracyclin</synonym>
    <synonym>Oxytetracycline</synonym>
    <synonym>Oxytetracycline (anhydrous)</synonym>
    <synonym>Oxytetracycline (internal use)</synonym>
    <synonym>Oxytetracycline [inn]</synonym>
    <synonym>Oxytetracycline amphoteric</synonym>
    <synonym>Oxytetracycline anhydrous</synonym>
    <synonym>Oxytetracycline calcium</synonym>
    <synonym>Oxytetracyclinum</synonym>
    <synonym>Pennox 200</synonym>
    <synonym>Proteroxyna</synonym>
    <synonym>Riomitsin</synonym>
    <synonym>Ryomycin</synonym>
    <synonym>Solkaciclina</synonym>
    <synonym>Stecsolin</synonym>
    <synonym>Stevacin</synonym>
    <synonym>Tarocyn</synonym>
    <synonym>Tarosin</synonym>
    <synonym>Teravit</synonym>
    <synonym>Terrafungine</synonym>
    <synonym>Terramitsin</synonym>
    <synonym>Terramycin</synonym>
    <synonym>Terramycin im</synonym>
    <synonym>Terramycin Q50</synonym>
    <synonym>Tetrachel</synonym>
    <synonym>Tetracycline, 5-hydroxy-</synonym>
    <synonym>Tetran</synonym>
    <synonym>Unimycin</synonym>
    <synonym>Ursocyclin</synonym>
    <synonym>Ursocycline</synonym>
    <synonym>Vendarcin</synonym>
  </synonyms>
  <chemical_formula>C22H24N2O9</chemical_formula>
  <average_molecular_weight>460.434</average_molecular_weight>
  <monisotopic_moleculate_weight>460.148180376</monisotopic_moleculate_weight>
  <iupac_name>4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboximidic acid</iupac_name>
  <traditional_iupac>4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboximidic acid</traditional_iupac>
  <cas_registry_number>79-57-2</cas_registry_number>
  <smiles>CN(C)C1C2C(O)C3C(=C(O)C2(O)C(=O)C(C(O)=N)=C1O)C(=O)C1=C(C=CC=C1O)C3(C)O</smiles>
  <inchi>InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)</inchi>
  <inchikey>IWVCMVBTMGNXQD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetracyclines. These are polyketides having an octahydrotetracene-2-carboxamide skeleton, substituted with many hydroxy and other groups.</description>
    <direct_parent>Tetracyclines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Tetracyclines</class>
    <sub_class/>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Anthracenecarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl ketones</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Naphthacenes</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Anthracene carboxylic acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Naphthacene</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>Polyol</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tetracene</substituent>
      <substituent>Tetracycline</substituent>
      <substituent>Tetralin</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.02e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 200 dec. (Me2CO solvate)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-6.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>-2.8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>13.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboximidic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>460.434</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>460.148180376</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN(C)C1C2C(O)C3C(=C(O)C2(O)C(=O)C(C(O)=N)=C1O)C(=O)C1=C(C=CC=C1O)C3(C)O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C22H24N2O9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>IWVCMVBTMGNXQD-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>202.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>126.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>44.56</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>8</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>
    <pathway>
      <name>Oxytetracycline Pathway</name>
      <smpdb_id>SMP00293</smpdb_id>
      <kegg_map_id></kegg_map_id>
    </pathway>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB14733</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id>OTC</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce3246d560&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3246d3a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3246d1f0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3246d038&gt;</reference>
    <reference>#&lt;Reference:0x000055ce3246ce80&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
