CHEBI:64321 - fosaprepitant

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ChEBI Name fosaprepitant
ChEBI ID CHEBI:64321
Definition A morpholine derivative that is the (1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl ether of (3-{[(2R,3S)-3-(4-fluorophenyl)-2-hydroxymorpholin-4-yl]methyl}-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H22F7N4O6P
Net Charge 0
Average Mass 614.40660
Monoisotopic Mass 614.11652
InChI InChI=1S/C23H22F7N4O6P/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)40-20-19(13-2-4-17(24)5-3-13)33(6-7-39-20)11-18-31-21(35)34(32-18)41(36,37)38/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38)/t12-,19+,20-/m1/s1
InChIKey BARDROPHSZEBKC-OITMNORJSA-N
SMILES C[C@@H](O[C@H]1OCCN(Cc2nn(c(=O)[nH]2)P(O)(O)=O)[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.
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.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing fosaprepitant (CHEBI:64321) has role antiemetic (CHEBI:50919)
fosaprepitant (CHEBI:64321) has role neurokinin-1 receptor antagonist (CHEBI:55350)
fosaprepitant (CHEBI:64321) has role prodrug (CHEBI:50266)
fosaprepitant (CHEBI:64321) is a (trifluoromethyl)benzenes (CHEBI:83565)
fosaprepitant (CHEBI:64321) is a cyclic acetal (CHEBI:59770)
fosaprepitant (CHEBI:64321) is a morpholines (CHEBI:38785)
fosaprepitant (CHEBI:64321) is a phosphoramide (CHEBI:17102)
fosaprepitant (CHEBI:64321) is a triazoles (CHEBI:35727)
fosaprepitant (CHEBI:64321) is conjugate acid of fosaprepitant(2−) (CHEBI:64322)
Incoming fosaprepitant(2−) (CHEBI:64322) is conjugate base of fosaprepitant (CHEBI:64321)
IUPAC Name
(3-{[(2R,3S)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid
INNs Sources
fosaprepitant ChemIDplus
fosaprépitant WHO MedNet
fosaprepitant WHO MedNet
fosaprepitantum WHO MedNet
Synonyms Sources
L-758,298 ChemIDplus
L-758298 ChemIDplus
Manual Xrefs Databases
4470 DrugCentral
DB06717 DrugBank
Fosaprepitant_dimeglumine Wikipedia
HMDB0015662 HMDB
US2010029592 Patent
View more database links
Registry Numbers Types Sources
172673-20-0 CAS Registry Number ChemIDplus
8601672 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19608812 PubMed citation Europe PMC
20795794 PubMed citation Europe PMC
21042544 PubMed citation Europe PMC
21209230 PubMed citation Europe PMC
21270665 PubMed citation Europe PMC
21383291 PubMed citation Europe PMC
21711119 PubMed citation Europe PMC
21947834 PubMed citation Europe PMC
22228030 PubMed citation Europe PMC
22316362 PubMed citation Europe PMC
Last Modified
22 February 2017