<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:42:50 UTC</creation_date>
  <update_date>2026-08-21 22:00:10 UTC</update_date>
  <accession/>
  <common_name>Losartan</common_name>
  <class>SmallMolecule</class>
  <description>Losartan (C22H23ClN6O) is a compound with an average molecular weight of 422.91 g/mol. Losartan belongs to the biphenyls and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It acts as an antagonist/stimulator of the Erythropoietin receptor (EPOR) and the Type-1 angiotensin II receptor (AGTR1).

The compound is used in the treatment of high blood pressure (PMC10698095), hypertension (PMC10997981, PMC12000610, PMC8673333, PMC9784116), essential hypertension (PMC4559490, PMC8424126), heart failure (PMC8424126), myocardial infarction (PMC7175553), diabetes mellitus (PMC7175553), hypokalemia (PMC8128374), and diarrhea (PMC8128374). Additionally, it has a therapeutic effect on hyperglycemia (PMC3399393) and stroke (PMC12000610).

Losartan has been found in or released from 29 recorded sources. These include aquatic systems and sediments such as seawater, freshwater, surface water, and groundwater; drinking water and water supply including tap water, bottled water, and desalinated water; and wastewater, sanitation and biosolids including wastewater treatment effluent, industrial wastewater, mine wastewater, and unspecified wastewater. It is also associated with household cleaning and consumer products such as tobacco smoke filters, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Further sources include electrical and electronic equipment such as electrodes, antennas, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials, as well as water heaters and water coolers from the appliances, HVAC and refrigerants sector, and 6 more sectors. Recorded exposure routes for the compound include touch, oral, and inhalation.</description>
  <categories/>
  <types>
    <type>PMT</type>
  </types>
  <synonyms>
    <synonym>[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol</synonym>
  </synonyms>
  <chemical_formula>C22H23ClN6O</chemical_formula>
  <average_molecular_weight>422.911</average_molecular_weight>
  <monisotopic_moleculate_weight>422.162187095</monisotopic_moleculate_weight>
  <iupac_name>[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol</iupac_name>
  <traditional_iupac>losartan</traditional_iupac>
  <cas_registry_number>114798-26-4</cas_registry_number>
  <smiles>CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1</smiles>
  <inchi>InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)</inchi>
  <inchikey>PSIFNNKUMBGKDQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Biphenyls and derivatives</sub_class>
    <direct_parent>Biphenyls and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>1,2,4,5-tetrasubstituted imidazoles</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenyltetrazoles and derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2,4,5-tetrasubstituted imidazole</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Biphenyl</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</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>Phenyltetrazole</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Tetrazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>biphenylyltetrazole</descriptor>
      <descriptor>imidazoles</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Losartan Action Pathway</name>
      <smpdb_id>SMP0000162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Losartan Angiotensin blocker Action Pathway</name>
      <smpdb_id>SMP0124963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Losartan Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143122</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>5</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.70e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>422.911</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>422.162187095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H23ClN6O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PSIFNNKUMBGKDQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>131.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</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>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f721bf73160&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00678</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3961</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>3824</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000062</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000654</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
  </targets>
</compound>
