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<compound>
  <id type="integer">2905</id>
  <title>T3D2863</title>
  <common-name>Amprenavir</common-name>
  <description>Amprenavir is an exogenous antiviral drug and HIV protease inhibitor with the chemical formula C25H35N3O6S. At room temperature, this compound exists as a solid. Amprenavir belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. With an average molecular weight of 505.63 g/mol, Amprenavir is a heavy molecule.

The compound is utilized as a biological and chemical HIV protease inhibitor. It has been recorded in seven sources, including healthcare, pharmaceuticals and veterinary products such as antivirals; household cleaning and consumer products, specifically non electric simulated smoking devices; and electrical and electronic equipment, including antennas, magnets, relays, television systems, and video games. The recorded route of exposure for this substance is oral.

In terms of protein targets, Amprenavir is an inhibitor of seven recorded proteins. These include the ATP-dependent translocase ABCB1, Cathepsin D (CTSD), Cytochrome P450 3A4 (CYP3A4), and Cytosolic 10-formyltetrahydrofolate dehydrogenase (ALDH1L1), along with three other proteins.</description>
  <cas>161814-49-9</cas>
  <pubchem-id>65016</pubchem-id>
  <chemical-formula>C25H35N3O6S</chemical-formula>
  <weight>505.224660</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>4.91e-02 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Rapidly absorbed after oral administration in HIV-1-infected patients with a time to peak concentration (T&lt;sub&gt;max&lt;/sub&gt;) typically between 1 and 2 hours after a single oral dose. The absolute oral bioavailability of amprenavir in humans has not been established.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Amprenavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.</mechanism-of-toxicity>
  <metabolism>Hepatic. Amprenavir is metabolized in the liver by the cytochrome P450 3A4 (CYP3A4) enzyme system. The 2 major metabolites result from oxidation of the tetrahydrofuran and aniline moieties. Glucuronide conjugates of oxidized metabolites have been identified as minor metabolites in urine and feces.Half Life: 7.1-10.6 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of HIV-1 infection in combination with other antiretroviral agents.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms></symptoms>
  <treatment>If overdosage occurs, the patient should be monitored for evidence of toxicity and standard supportive treatment applied as necessary. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:27Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:46:28Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Amprenavir</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C08086</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>2684</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Amprenavir</stitch-id>
  <drugbank-id>DB00701</drugbank-id>
  <pdb-id>478</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1</moldb-smiles>
  <moldb-formula>C25H35N3O6S</moldb-formula>
  <moldb-inchi>InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1</moldb-inchi>
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  <moldb-average-mass type="decimal">505.627</moldb-average-mass>
  <moldb-mono-mass type="decimal">505.224656557</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.43</logp>
  <hmdb-id>HMDB14839</hmdb-id>
  <chembl-id>CHEMBL116</chembl-id>
  <chemspider-id>58532</chemspider-id>
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  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;&lt;a href="http://www.drugsyn.org/Amprenavir.htm"&gt;DrugSyn.org&lt;/a&gt;&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002251</chemdb-id>
  <dsstox-id>DTXSID5046061</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00004082</susdat-id>
  <iupac>(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate</iupac>
  <moldb-polar-surface-area>131.19</moldb-polar-surface-area>
  <moldb-refractivity>134.0815</moldb-refractivity>
  <moldb-polarizability>53.60424163797374</moldb-polarizability>
  <moldb-rotatable-bond-count>11</moldb-rotatable-bond-count>
  <moldb-acceptor-count>6</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>13.614255356778301</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>2.3863099248148067</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>1.85</moldb-alogps-logp>
  <moldb-alogps-logs>-4.01</moldb-alogps-logs>
  <moldb-alogps-solubility>4.91e-02 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Benzenoids</superklass>
  <klass>Benzene and substituted derivatives</klass>
  <subklass>Benzenesulfonamides</subklass>
  <paper-count type="integer">902</paper-count>
  <sync-id>CED0005536</sync-id>
  <structure-inchikey>YMARZQAQMVYCKC-OEMFJLHTSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:37Z</structure-indexed-at>
</compound>
