nevirapine   Click here for help

GtoPdb Ligand ID: 12676

Synonyms: BI-RG-587 | BIRG-587 | BIRG587 | NVP | Viramune®
Approved drug PDB Ligand
nevirapine is an approved drug (FDA (1996), EMA (1998))
Compound class: Synthetic organic
Comment: Nevirapine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) class antiretriviral drug.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 57.06
Molecular weight 266.3
XLogP 0.51
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES CC1=CC=NC2=C1NC(=O)C3=CC=CN=C3N2C4CC4
Isomeric SMILES CC1=C2C(=NC=C1)N(C3=C(C=CC=N3)C(=O)N2)C4CC4
InChI InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)
InChI Key NQDJXKOVJZTUJA-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996), EMA (1998))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
4-amino-1-[(2R,4R)-2-(hydroxymethyl)-1,3-oxathiolan-4-yl]pyrimidin-2-one
International Nonproprietary Names Click here for help
INN number INN
6815 nevirapine
Synonyms Click here for help
BI-RG-587 | BIRG-587 | BIRG587 | NVP | Viramune®
Database Links Click here for help
BindingDB Ligand 1434
ChEBI CHEBI:63613
ChEMBL Ligand CHEMBL57
DrugBank Ligand DB00238
GtoPdb PubChem SID 483123224
PubChem CID 4463
RCSB PDB Ligand NVP
Search Google for chemical match using the InChIKey NQDJXKOVJZTUJA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NQDJXKOVJZTUJA
Search PubMed clinical trials nevirapine
Search PubMed titles nevirapine
Search PubMed titles/abstracts nevirapine
UniChem Compound Search for chemical match using the InChIKey NQDJXKOVJZTUJA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NQDJXKOVJZTUJA-UHFFFAOYSA-N