<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 03:28:10 UTC</creation_date>
  <update_date>2026-08-18 03:25:42 UTC</update_date>
  <accession/>
  <common_name>Ethambutol</common_name>
  <class>SmallMolecule</class>
  <description>Ethambutol is an organic compound with the chemical formula C10H24N2O2 and an average molecular weight of 204.31 g/mol. Ethambutol belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. It is identified as an antibiotic and a drug used for the treatment of tuberculosis. The compound acts as an inhibitor of three recorded protein targets: Probable arabinosyltransferase A (embA), Probable arabinosyltransferase B (embB), and Probable arabinosyltransferase C (embC).

This substance is found in or released from 20 recorded sources across various categories. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as an antibiotic and for the treatment of tuberculosis. It is also associated with food, food processing, and cookware, specifically in the processing of meats. Other recorded sources include household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and two additional items. Furthermore, it is found in electrical and electronic equipment, including electric switches, antennas, amplifiers, electric hearing aids, electrically stimulated smoking devices, and five other sources. Recorded exposure routes for ethambutol include oral and inhalation.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C10H24N2O2</chemical_formula>
  <average_molecular_weight>204.3098</average_molecular_weight>
  <monisotopic_moleculate_weight>204.183778022</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol</iupac_name>
  <traditional_iupac>ethambutol</traditional_iupac>
  <cas_registry_number>74-55-5</cas_registry_number>
  <smiles>CC[C@@H](CO)NCCN[C@@H](CC)CO</smiles>
  <inchi>InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1</inchi>
  <inchikey>AEUTYOVWOVBAKS-UWVGGRQHSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>1,2-aminoalcohols</direct_parent>
    <alternate_parents>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>ethanolamines</descriptor>
      <descriptor>ethylenediamine derivative</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Ethambutol Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethambutol Action Pathway</name>
      <smpdb_id>SMP0718083</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.059</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.58e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.059</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-[(2-{[(2S)-1-hydroxybutan-2-yl]amino}ethyl)amino]butan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>204.3098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>204.183778022</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@@H](CO)NCCN[C@@H](CC)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H24N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H24N2O2/c1-3-9(7-13)11-5-6-12-10(4-2)8-14/h9-14H,3-8H2,1-2H3/t9-,10-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AEUTYOVWOVBAKS-UWVGGRQHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>64.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72a996dc00&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00330</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>14052</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>13433</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
