<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:32:18 UTC</creation_date>
  <update_date>2015-10-09 22:33:06 UTC</update_date>
  <accession>FDB023605</accession>
  <name>Citalopram</name>
  <description>Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety; Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). It is sold under the brand-names Celexa (U.S., Forest Laboratories, Inc.), Cipramil, Seropram (Europe and Australia) and Ciazil (Australia); A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition; Citalopram is an antidepressant drug used to treat depression associated with mood disorders. It is also used on occasion in the treatment of body dysmorphic disorder and anxiety.
Citalopram belongs to a class of drugs known as selective serotonin reuptake inhibitors (SSRIs). [HMDB]</description>
  <synonyms>
    <synonym>Bonitrile</synonym>
    <synonym>Celexa</synonym>
    <synonym>Citadur</synonym>
    <synonym>Citalopram hydrobromide</synonym>
    <synonym>Nitalapram</synonym>
  </synonyms>
  <chemical_formula>C20H21FN2O</chemical_formula>
  <average_molecular_weight>324.3919</average_molecular_weight>
  <monisotopic_moleculate_weight>324.163791509</monisotopic_moleculate_weight>
  <iupac_name>1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile</iupac_name>
  <traditional_iupac>recital</traditional_iupac>
  <cas_registry_number>59729-33-8</cas_registry_number>
  <smiles>CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1</smiles>
  <inchi>InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3</inchi>
  <inchikey>WSEQXVZVJXJVFP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.</description>
    <direct_parent>Phenylbutylamines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylbutylamines</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl fluorides</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Fluorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isocoumarans</alternative_parent>
      <alternative_parent>Nitriles</alternative_parent>
      <alternative_parent>Organofluorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aryl fluoride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Carbonitrile</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Fluorobenzene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isocoumaran</substituent>
      <substituent>Nitrile</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organofluoride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phenylbutylamine</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>2-benzofurans</external_descriptor>
      <external_descriptor>cyclic ether</external_descriptor>
      <external_descriptor>nitrile</external_descriptor>
      <external_descriptor>organofluorine compound</external_descriptor>
      <external_descriptor>tertiary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.88e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>3.76</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>324.3919</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>324.163791509</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN(C)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C20H21FN2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>WSEQXVZVJXJVFP-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>36.26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>94.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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::EiMs</type>
      <spectrum_id>568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>124990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>131650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>139384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61685</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
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      <spectrum_id>118258</spectrum_id>
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      <spectrum_id>118259</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441061</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>441062</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>441063</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441064</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443252</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443253</spectrum_id>
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    <spectrum>
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      <spectrum_id>443254</spectrum_id>
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      <spectrum_id>443255</spectrum_id>
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    <spectrum>
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      <spectrum_id>443256</spectrum_id>
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      <spectrum_id>443257</spectrum_id>
    </spectrum>
    <spectrum>
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    </spectrum>
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    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443260</spectrum_id>
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    <spectrum>
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      <spectrum_id>443264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443265</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB05038</hmdb_id>
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  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
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  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Cytochrome P450 2D6</name>
      <uniprot_id>Q6NWU0</uniprot_id>
      <uniprot_name/>
      <gene_name>CYP2D6</gene_name>
    </enzyme>
    <enzyme>
      <name>Cytochrome P450, family 1, subfamily A, polypeptide 1</name>
      <uniprot_id>A0N0X8</uniprot_id>
      <uniprot_name/>
      <gene_name>CYP1A1</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
