aprepitant   

GtoPdb Ligand ID: 3490

Synonyms: Emend®
aprepitant is an approved drug (FDA and EMA (2003))
Compound class: Synthetic organic
Comment: Aprepitant is a NK1 receptor antagonist.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: aprepitant

2D Structure
Click here for structure editor
Physico-chemical Properties
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
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
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
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
INN number INN
8050 aprepitant
Synonyms
Emend®
Database Links
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 6918365
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
Search UniChem for chemical match using the InChIKey ATALOFNDEOCMKK-OITMNORJSA-N
Search UniChem for chemicals with the same backbone ATALOFNDEOCMKK
Wikipedia Aprepitant

Product suppliers

View disclaimer

Tocris
Aprepitant
Cat. No. 6486