aprepitant   Click here for help

GtoPdb Ligand ID: 3490

Synonyms: Aponvie® | Emend®
Approved drug PDB Ligand
aprepitant is an approved drug (FDA and EMA (2003))
Compound class: Synthetic organic
Comment: Aprepitant is a NK1 receptor antagonist.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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aprepitant 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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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 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 83.24
Molecular weight 534.15
XLogP 5.31
No. Lipinski's rules broken 1
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 Fc1ccc(cc1)C1C(OCCN1Cc1[nH][nH]c(=O)n1)OC(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
Isomeric SMILES Fc1ccc(cc1)[C@H]1[C@H](OCCN1Cc1[nH][nH]c(=O)n1)O[C@@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C
InChI InChI=1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35)/t12-,19+,20-/m1/s1
InChI Key ATALOFNDEOCMKK-OITMNORJSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA and EMA (2003))
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.
Prodrug fosaprepitant
IUPAC Name Click here for help
5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one
International Nonproprietary Names Click here for help
INN number INN
8050 aprepitant
Synonyms Click here for help
Aponvie® | Emend®
Database Links Click here for help
Specialist databases
GPCRdb Ligand aprepitant
Other databases
CAS Registry No. 170729-80-3 (source: Scifinder)
ChEBI CHEBI:499361
ChEMBL Ligand CHEMBL1471
DrugBank Ligand DB00673
DrugCentral Ligand 230
GtoPdb PubChem SID 178100479
PubChem CID 135413536
RCSB PDB Ligand GBQ
Search Google for chemical match using the InChIKey ATALOFNDEOCMKK-OITMNORJSA-N
Search Google for chemicals with the same backbone ATALOFNDEOCMKK
Search PubMed clinical trials aprepitant
Search PubMed titles aprepitant
Search PubMed titles/abstracts aprepitant
UniChem Compound Search for chemical match using the InChIKey ATALOFNDEOCMKK-OITMNORJSA-N
UniChem Connectivity Search for chemical match using the InChIKey ATALOFNDEOCMKK-OITMNORJSA-N
Wikipedia Aprepitant

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Tocris
Aprepitant (links to external site)
Cat. No. 6486