<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:31:51 UTC</creation_date>
  <update_date>2015-10-09 22:32:02 UTC</update_date>
  <accession>FDB023576</accession>
  <name>Loperamide</name>
  <description>Loperamide is an opioid receptor agonist and acts on the mu opioid receptors in the myenteric plexus large intestines; it does not affect the central nervous system like other opioids; Loperamide usually as hydrochloride, is a drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. In most countries it is available generically under brand names such as Lopex, Imodium, Dimor and Pepto Diarrhea Control; Treatment should be avoided in the presence of fever or if the stool is bloody. Treatment is not recommended for patients who could suffer detrimental effects from rebound constipation. If there is a suspicion of diarrhea associated with organisms that can penetrate the intestinal walls, such as E. coli O157:H7 or salmonella, loperamide is contraindicated; Loperamide, usually as hydrochloride, is a drug effective against diarrhea resulting from gastroenteritis or inflammatory bowel disease. In most countries it is available generically under brand names such as Lopex, Imodium, Dimor and Pepto Diarrhea Control; it does not affect the central nervous system like other opioids; One of the long-acting synthetic antidiarrheals; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally; Loperamide is an opioid receptor agonist and acts on the mu opioid receptors in the myenteric plexus large intestines [HMDB]</description>
  <synonyms>
    <synonym>Apo-Loperamide</synonym>
    <synonym>Imodium A-D</synonym>
    <synonym>Imodium A-D Caplets</synonym>
    <synonym>Kaopectate II</synonym>
    <synonym>Loperacap</synonym>
    <synonym>Loperamida</synonym>
    <synonym>Loperamide hydrochloride</synonym>
    <synonym>Loperamidum</synonym>
    <synonym>Maalox Anti-Diarrheal</synonym>
    <synonym>Nu-Loperamide</synonym>
    <synonym>PMS-Loperamide</synonym>
    <synonym>Rho-Loperamide</synonym>
  </synonyms>
  <chemical_formula>C29H33ClN2O2</chemical_formula>
  <average_molecular_weight>477.038</average_molecular_weight>
  <monisotopic_moleculate_weight>476.223056017</monisotopic_moleculate_weight>
  <iupac_name>4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide</iupac_name>
  <traditional_iupac>imodium</traditional_iupac>
  <cas_registry_number>53179-11-6</cas_registry_number>
  <smiles>CN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3</inchi>
  <inchikey>RDOIQAHITMMDAJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.</description>
    <direct_parent>Diphenylmethanes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Diphenylmethanes</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylacetamides</alternative_parent>
      <alternative_parent>Phenylpiperidines</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Diphenylmethane</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylacetamide</substituent>
      <substituent>Phenylpiperidine</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid amide</external_descriptor>
      <external_descriptor>monochlorobenzenes</external_descriptor>
      <external_descriptor>piperidines</external_descriptor>
      <external_descriptor>tertiary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.60e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.77</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>13.96</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.41</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>477.038</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>476.223056017</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN(C)C(=O)C(CCN1CCC(O)(CC1)C1=CC=C(Cl)C=C1)(C1=CC=CC=C1)C1=CC=CC=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C29H33ClN2O2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C29H33ClN2O2/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23/h3-16,34H,17-22H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>RDOIQAHITMMDAJ-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>43.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>139.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>52.59</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>1</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::NmrTwoD</type>
      <spectrum_id>1949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>132826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>140560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244847</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB04999</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x00007f093c18d548&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c18d340&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c18d188&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>DNA-3-methyladenine glycosylase</name>
      <uniprot_id>P29372</uniprot_id>
      <uniprot_name/>
      <gene_name>MPG</gene_name>
    </enzyme>
    <enzyme>
      <name>Glucose 1,6-bisphosphate synthase</name>
      <uniprot_id>Q6PCE3</uniprot_id>
      <uniprot_name/>
      <gene_name>PGM2L1</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
