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CHEBI:499361 - aprepitant

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ChEBI Name aprepitant
ChEBI ID CHEBI:499361
Definition A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/neurokinin 1 (NK1) receptors.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H21F7N4O3
Net Charge 0
Average Mass 534.42670
Monoisotopic Mass 534.150
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
InChIKey ATALOFNDEOCMKK-OITMNORJSA-N
SMILES C[C@@H](O[C@H]1OCCN(Cc2n[nH]c(=O)[nH]2)[C@H]1c1ccc(F)cc1)c1cc(cc(c1)C(F)(F)F)C(F)(F)F
Roles Classification
Biological Role(s): neurokinin-1 receptor antagonist
An antagonist at the neurokinin-1 receptor.
substance P receptor antagonist
An antagonist at the substance P receptor.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aprepitant (CHEBI:499361) has role antidepressant (CHEBI:35469)
aprepitant (CHEBI:499361) has role antiemetic (CHEBI:50919)
aprepitant (CHEBI:499361) has role neurokinin-1 receptor antagonist (CHEBI:55350)
aprepitant (CHEBI:499361) has role peripheral nervous system drug (CHEBI:49110)
aprepitant (CHEBI:499361) has role substance P receptor antagonist (CHEBI:55351)
aprepitant (CHEBI:499361) is a (trifluoromethyl)benzenes (CHEBI:83565)
aprepitant (CHEBI:499361) is a cyclic acetal (CHEBI:59770)
aprepitant (CHEBI:499361) is a morpholines (CHEBI:38785)
aprepitant (CHEBI:499361) is a triazoles (CHEBI:35727)
IUPAC Name
5-{[(2R,3S)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholin-4-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
INNs Sources
aprepitant KEGG DRUG
aprépitant WHO MedNet
aprepitant WHO MedNet
aprepitantum WHO MedNet
Synonym Source
3-(((2R,3S)-3-(p-Fluorophenyl)-2-(((αR)-α-methyl-3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-Δ2-1,2,4-triazolin-5-one ChemIDplus
Database Links Databases
Aprepitant Wikipedia
D02968 KEGG DRUG
DB00673 DrugBank
HMDB14811 HMDB
LSM-5637 LINCS
View more database links
Registry Numbers Types Sources
170729-80-3 CAS Registry Number KEGG DRUG
170729-80-3 CAS Registry Number DrugBank
170729-80-3 CAS Registry Number ChemIDplus
8096869 Beilstein Registry Number Beilstein
8096869 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
21415280 PubMed citation Europe PMC
22141732 PubMed citation Europe PMC
22187110 PubMed citation Europe PMC
22260216 PubMed citation Europe PMC
22995650 PubMed citation Europe PMC
23062719 PubMed citation Europe PMC
23191934 PubMed citation Europe PMC
23370141 PubMed citation Europe PMC
23560185 PubMed citation Europe PMC
Last Modified
25 February 2016