aprepitant   Click here for help

GtoPdb Ligand ID: 3490

Synonyms: 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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2D Structure
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Physico-chemical Properties
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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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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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
Emend®
Database Links Click here for help
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
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Wikipedia Aprepitant

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Tocris
Aprepitant
Cat. No. 6486