CHEBI:90908 - rolapitant

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name rolapitant
ChEBI ID CHEBI:90908
Definition An azaspiro compound that is 1,7-diazaspiro[4.5]decan-2-one carrying additional phenyl and 1-{[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl substituents at position 8. Used (in the form of the hydrochloride hydrate) for the prevention of delayed nausea and vomiting associated with initial and repeat courses of emetogenic cancer chemotherapy.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C25H26F6N2O2
Net Charge 0
Average Mass 500.477
Monoisotopic Mass 500.18985
InChI InChI=1S/C25H26F6N2O2/c1-16(17-11-19(24(26,27)28)13-20(12-17)25(29,30)31)35-15-23(18-5-3-2-4-6-18)10-9-22(14-32-23)8-7-21(34)33-22/h2-6,11-13,16,32H,7-10,14-15H2,1H3,(H,33,34)/t16-,22-,23-/m1/s1
InChIKey FIVSJYGQAIEMOC-ZGNKEGEESA-N
SMILES C1=C(C=C(C=C1C(F)(F)F)C(F)(F)F)[C@H](OC[C@@]2(NC[C@]3(CC2)CCC(N3)=O)C4=CC=CC=C4)C
Roles Classification
Biological Role(s): neurokinin-1 receptor antagonist
An antagonist at the neurokinin-1 receptor.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rolapitant (CHEBI:90908) has role antiemetic (CHEBI:50919)
rolapitant (CHEBI:90908) has role neurokinin-1 receptor antagonist (CHEBI:55350)
rolapitant (CHEBI:90908) is a azaspiro compound (CHEBI:35624)
rolapitant (CHEBI:90908) is a ether (CHEBI:25698)
rolapitant (CHEBI:90908) is a organofluorine compound (CHEBI:37143)
rolapitant (CHEBI:90908) is a piperidines (CHEBI:26151)
rolapitant (CHEBI:90908) is a pyrrolidin-2-ones (CHEBI:74223)
rolapitant (CHEBI:90908) is conjugate base of rolapitant(1+) (CHEBI:90913)
Incoming rolapitant(1+) (CHEBI:90913) is conjugate acid of rolapitant (CHEBI:90908)
IUPAC Name
(5S,8S)-8-({(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}methyl)-8-phenyl-1,7-diazaspiro[4.5]decan-2-one
INN Source
rolapitant KEGG DRUG
Synonyms Sources
SCH 619734 ChemIDplus
SCH-619734 ChemIDplus
Manual Xrefs Databases
5027 DrugCentral
D10742 KEGG DRUG
View more database links
Registry Numbers Types Sources
15570068 Reaxys Registry Number Reaxys
552292-08-7 CAS Registry Number ChemIDplus
552292-08-7 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
22497992 PubMed citation Europe PMC
24874107 PubMed citation Europe PMC
25755107 PubMed citation Europe PMC
25856052 PubMed citation Europe PMC
25940030 PubMed citation Europe PMC
26272768 PubMed citation Europe PMC
26272769 PubMed citation Europe PMC
26366937 PubMed citation Europe PMC
26442475 PubMed citation Europe PMC
26467681 PubMed citation Europe PMC
26694923 PubMed citation Europe PMC
26699406 PubMed citation Europe PMC
Last Modified
22 February 2017