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fosamprenavir   Click here for help

GtoPdb Ligand ID: 12682

Synonyms: FOS-APV | GW-433908 | GW433908 | Lexiva® | VX-175 | VX175
Approved drug
fosamprenavir is an approved drug (FDA (2003), EMA (2004))
Compound class: Synthetic organic
Comment: Fosamprenavir is a prodrug of the HIV-1 protease inhibitor and antiretroviral drug amprenavir.

fosamprenavir is commercially available from our sponsors

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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 12
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 195.91
Molecular weight 585.61
XLogP -0.08
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)OP(=O)(O)O)S(=O)(=O)C3=CC=C(C=C3)N
Isomeric SMILES CC(C)CN(C[C@H]([C@H](CC1=CC=CC=C1)NC(=O)O[C@H]2CCOC2)OP(=O)(O)O)S(=O)(=O)C3=CC=C(C=C3)N
InChI InChI=1S/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1
InChI Key MLBVMOWEQCZNCC-OEMFJLHTSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EU EMA (2004)  |  US FDA (2003)
Is prodrug? Yes
Active form amprenavir
IUPAC Name Click here for help
[(3S)-oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
8011 fosamprenavir
Synonyms Click here for help
FOS-APV | GW-433908 | GW433908 | Lexiva® | VX-175 | VX175
Database Links Click here for help
GtoPdb PubChem SID 483123230
PubChem CID 131536
Search Google for chemical match using the InChIKey MLBVMOWEQCZNCC-OEMFJLHTSA-N
Search Google for chemicals with the same backbone MLBVMOWEQCZNCC
Search PubMed clinical trials fosamprenavir
Search PubMed titles fosamprenavir
Search PubMed titles/abstracts fosamprenavir
UniChem Compound Search for chemical match using the InChIKey MLBVMOWEQCZNCC-OEMFJLHTSA-N
UniChem Connectivity Search for chemical match using the InChIKey MLBVMOWEQCZNCC-OEMFJLHTSA-N

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MedChemExpress
Fosamprenavir (links to external site)
Cat. No. HY-78726