stavudine   Click here for help

GtoPdb Ligand ID: 12678

Synonyms: BMY-27857 | BMY27857 | d4T | STV | Zerit®
Approved drug
stavudine is an approved drug (FDA (1994))
Compound class: Synthetic organic
Comment: Stavudine is a nucleoside reverse transcriptase inhibitors (NRTI) class antiretriviral agent. It is a thymidine analogue.

stavudine 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 6
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 78.87
Molecular weight 224.21
XLogP -0.72
No. Lipinski's rules broken 0

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 CC1=CN([C@H]2C=C[C@@H](CO)O2)C(=O)NC1=O
Isomeric SMILES CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
InChI InChI=1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1
InChI Key XNKLLVCARDGLGL-JGVFFNPUSA-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. FDA (1994)
Withdrawn drug? Yes
IUPAC Name Click here for help
1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
6775 stavudine
Synonyms Click here for help
BMY-27857 | BMY27857 | d4T | STV | Zerit®
Database Links Click here for help
BindingDB Ligand 50013111
ChEBI CHEBI:63581
ChEMBL Ligand CHEMBL991
DrugBank Ligand DB00649
GtoPdb PubChem SID 483123226
PubChem CID 18283
Search Google for chemical match using the InChIKey XNKLLVCARDGLGL-JGVFFNPUSA-N
Search Google for chemicals with the same backbone XNKLLVCARDGLGL
Search PubMed clinical trials stavudine
Search PubMed titles stavudine
Search PubMed titles/abstracts stavudine
UniChem Compound Search for chemical match using the InChIKey XNKLLVCARDGLGL-JGVFFNPUSA-N
UniChem Connectivity Search for chemical match using the InChIKey XNKLLVCARDGLGL-JGVFFNPUSA-N

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MedChemExpress
Stavudine (links to external site)
Cat. No. HY-B0116
Stavudine (Standard) (links to external site)
Cat. No. HY-B0116R