tipranavir   Click here for help

GtoPdb Ligand ID: 12685

Synonyms: Aptivus® | PNU-140690 | TPV | U-140690
Approved drug PDB Ligand
tipranavir is an approved drug (FDA & EMA (2005))
Compound class: Synthetic organic
Comment: Tipranavir is an anti-HIV-1 agent. It inhibits the viral protease.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 113.44
Molecular weight 602.67
XLogP 5.13
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC[C@@]1(CCC2=CC=CC=C2)CC(=C([C@H](CC)C3=CC=CC(=C3)NS(=O)(=O)C4=CC=C(C=N4)C(F)(F)F)C(=O)O1)O
Isomeric SMILES CCC[C@]1(CC(=C(C(=O)O1)[C@H](CC)C2=CC(=CC=C2)NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)O)CCC4=CC=CC=C4
InChI InChI=1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
InChI Key SUJUHGSWHZTSEU-FYBSXPHGSA-N
No information available.
Summary of Clinical Use Click here for help
Tipranavir was used in the treatment of HIV-1 infection, although its use has largely been superceded in the clinic. In use, it is prescribed alongside ritonavir (to inhibit CYP3A4-mediated tipranavir metabolism) and other HIV antiviral drugs.
External links Click here for help
For extended ADME data see the following:

Drugs.com
European Medicines Agency (EMA)