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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1471
CHEMBL1471
Compound Name APREPITANT
ChEMBL Synonyms MK-869 | APREPITANT | EMEND | MK-0869 | CINVANTI
Max Phase 4 (Approved)
Trade Names EMEND | APREPITANT | CINVANTI
Molecular Formula C23H21F7N4O3

Additional synonyms for CHEMBL1471 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@@H](O[C@H]1OCCN(CC2=NNC(=O)N2)[C@H]1c3ccc(F)cc3)c4cc(cc( ...
Download SMILES
Standard InChI InChI=1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)2 ...
Download InChI
Standard InChI Key ATALOFNDEOCMKK-OITMNORJSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Orange Book
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1471

Molecule Features

CHEMBL1471 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:Y Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Neurokinin 1 receptor antagonist Neurokinin 1 receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Depressive DisorderD003866EFO:0003761unipolar depression3ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
NauseaD009325EFO:0006911Chemotherapy-induced nausea and vomiting4ClinicalTrials
DailyMed
DailyMed
DailyMed
NeoplasmsD009369EFO:0000311cancer2ClinicalTrials
AlcoholismD000437EFO:0003829alcohol dependence2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Postoperative Nausea and VomitingD020250EFO:0004888post operative nausea and vomiting4ClinicalTrials
DailyMed
DailyMed
DailyMed
Postoperative Nausea and VomitingD020250HP:0002017Nausea and vomiting4ClinicalTrials
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
Marijuana AbuseD002189EFO:0004218marijuana dependence2ClinicalTrials
NauseaD009325HP:0002018Nausea4ATC
ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
GastroparesisD018589EFO:1000948gastroparesis3ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Heroin DependenceD006556EFO:0004240heroin dependence1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
PruritusD011537HP:0000989Pruritus2ClinicalTrials
Opioid-Related DisordersD009293EFO:0005611opioid dependence1ClinicalTrials
VomitingD0148393ClinicalTrials

Clinical Data

ClinicalTrials.gov APREPITANT
The Cochrane Collaboration APREPITANT

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1471. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL249 Neurokinin 1 receptor Homo sapiens 1.000
CHEMBL4027 Neurokinin 1 receptor Rattus norvegicus 0.510
CHEMBL2327 Neurokinin 2 receptor Homo sapiens 0.475

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL249 Neurokinin 1 receptor Homo sapiens 1.000
CHEMBL240 HERG Homo sapiens 0.932
CHEMBL2327 Neurokinin 2 receptor Homo sapiens 0.928
CHEMBL4027 Neurokinin 1 receptor Rattus norvegicus 0.225

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
534.4 534.1502 4.95 6 83.24 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 2 1 7 2 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
8.06 4.38 4.99 4.84 3 37 0.44

Structural Alerts

There are 2 structural alerts for CHEMBL1471. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A04 - ANTIEMETICS AND ANTINAUSEANTS
A04A - ANTIEMETICS AND ANTINAUSEANTS
A04AD - Other antiemetics
A04AD12 - aprepitant

ChemSpider ChemSpider:ATALOFNDEOCMKK-OITMNORJSA-N
DailyMed aprepitant
Wikipedia Aprepitant

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1471



BindingDB 50220136
ChEBI 499361
ChemicalBook CB7500857
DrugBank DB00673
DrugCentral 230
eMolecules 30153720 8763262
EPA CompTox Dashboard DTXSID3049047
FDA SRS 1NF15YR6UY
Guide to Pharmacology 3490
Human Metabolome Database HMDB0014811
IBM Patent System 72C6E1430FC62BABEBE02599CC63DF96
LINCS LSM-5637
MolPort MolPort-009-679-399 MolPort-006-392-367
Nikkaji J1.059.639D
PDBe GBQ
PubChem 6918365
PubChem: Drugs of the Future 12015114
PubChem: Thomson Pharma 14787735 14812125 14861083
Selleck Aprepitant
SureChEMBL SCHEMBL264924
ZINC ZINC000027428713

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/ATALOFNDEOCMKK-OITMNORJSA-N spacer
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