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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL116
CHEMBL116
Compound Name AMPRENAVIR
ChEMBL Synonyms 141 W94 | VX-478 | KVX-478 | AGENERASE | AMPRENAVIR | 141W94
Max Phase 4 (Approved)
Trade Names AGENERASE
Molecular Formula C25H35N3O6S

Additional synonyms for CHEMBL116 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]2CCOC2)S(=O)(= ...
Download SMILES
Standard InChI InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9- ...
Download InChI
Standard InChI Key YMARZQAQMVYCKC-OEMFJLHTSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL116

Molecule Features

CHEMBL116 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Human immunodeficiency virus type 1 protease inhibitor Human immunodeficiency virus type 1 protease FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
HIV InfectionsD015658EFO:0000764HIV infection3ClinicalTrials
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS1ClinicalTrials

Clinical Data

ClinicalTrials.gov AMPRENAVIR
The Cochrane Collaboration AMPRENAVIR

Metabolites for CHEMBL116

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL116. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL243 Human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 1.000
CHEMBL2366517 Protease Human immunodeficiency virus 1 1.000
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.996
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.981
CHEMBL340 Cytochrome P450 3A4 Homo sapiens 0.931
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.841
CHEMBL2857 Human rhinovirus A protease Human rhinovirus sp. 0.804
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.720
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.677
CHEMBL2581 Cathepsin D Homo sapiens 0.293



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL243 Human immunodeficiency virus type 1 protease Human immunodeficiency virus 1 1.000
CHEMBL2366517 Protease Human immunodeficiency virus 1 1.000
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.998
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.994
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.966
CHEMBL2581 Cathepsin D Homo sapiens 0.948
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.879
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.781

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
505.6 505.2247 2.4 11 131.19 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 3 1 9 4 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.54 1.76 2.68 2.68 2 35 0.4

Structural Alerts

There are 6 structural alerts for CHEMBL116. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J05 - ANTIVIRALS FOR SYSTEMIC USE
J05A - DIRECT ACTING ANTIVIRALS
J05AE - Protease inhibitors
J05AE05 - amprenavir

ChemSpider ChemSpider:YMARZQAQMVYCKC-OEMFJLHTSA-N
Wikipedia Amprenavir

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL116



BindingDB 577 50215393
Brenda 1608
ChEBI 40050
ChemicalBook CB4186139
DrugBank DB00701
DrugCentral 200
eMolecules 877446
FDA SRS 5S0W860XNR
Human Metabolome Database HMDB0014839
IBM Patent System 7152EF97E47AEF2F4BE48228D6AB587E
KEGG Ligand C08086
Mcule MCULE-8147835017
MolPort MolPort-000-883-856
Nikkaji J1.015.291G
PDBe 478
PharmGKB PA448422
PubChem 65016
PubChem: Drugs of the Future 12014852
PubChem: Thomson Pharma 14835820 14884574
Selleck Amprenavir-(Agenerase)
SureChEMBL SCHEMBL34151
ZINC ZINC000003809192

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/YMARZQAQMVYCKC-OEMFJLHTSA-N spacer
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