478

{3-[(4-AMINO-BENZENESULFONYL)-ISOBUTYL-AMINO]-1-BENZYL-2-HYDROXY-PROPYL}-CARBAMIC ACID TETRAHYDRO-FURAN-3-YL ESTER

Created: 1999-07-08
Last modified:  2020-06-05

Help

Find related ligands:

Chemical Details

Formal Charge0
Atom Count70
Chiral Atom Count3
Bond Count72
Aromatic Bond Count12
2D diagram of 478
Toggle HydrogenToggle Labels

Chemical Component Summary

Name{3-[(4-AMINO-BENZENESULFONYL)-ISOBUTYL-AMINO]-1-BENZYL-2-HYDROXY-PROPYL}-CARBAMIC ACID TETRAHYDRO-FURAN-3-YL ESTER
SynonymsAmprenavir
Systematic Name (OpenEye OEToolkits)[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenyl-butan-2-yl]carbamate
FormulaC25 H35 N3 O6 S
Molecular Weight505.627
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(OC1CCOC1)NC(Cc2ccccc2)C(O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3
SMILESCACTVS3.370CC(C)CN(C[CH](O)[CH](Cc1ccccc1)NC(=O)O[CH]2CCOC2)[S](=O)(=O)c3ccc(N)cc3
SMILESOpenEye OEToolkits1.7.0CC(C)CN(CC(C(Cc1ccccc1)NC(=O)OC2CCOC2)O)S(=O)(=O)c3ccc(cc3)N
Canonical SMILESCACTVS3.370 CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]2CCOC2)[S](=O)(=O)c3ccc(N)cc3
Canonical SMILESOpenEye OEToolkits1.7.0 CC(C)C[N@](C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@H]2CCOC2)O)S(=O)(=O)c3ccc(cc3)N
InChIInChI1.03 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
InChIKeyInChI1.03 YMARZQAQMVYCKC-OEMFJLHTSA-N

Drug Info: DrugBank

DrugBank IDDB00701 
NameAmprenavir
Groups
  • approved
  • investigational
DescriptionAmprenavir is a protease inhibitor used to treat HIV infection.
Synonyms
  • Amprénavir
  • (3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate
  • Amprenavir
  • Amprenavirum
Brand NamesAgenerase
IndicationFor the treatment of HIV-1 infection in combination with other antiretroviral agents.
Categories
  • Acids, Acyclic
  • Amides
  • Amprenavir and Prodrugs
  • Anti-HIV Agents
  • Anti-Infective Agents
ATC-CodeJ05AE05
CAS number161814-49-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Human immunodeficiency virus type 1 proteasePQVTLWQRPLVTIKIGGQLKEALLDTGADDTVLEEMSLPGRWKPKMIGGI...unknowninhibitor
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknowninhibitor
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL116
PubChem 65016
ChEMBL CHEMBL116
ChEBI CHEBI:40050