CHEBI:77590 - armodafinil

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name armodafinil
ChEBI ID CHEBI:77590
Definition A 2-[(diphenylmethyl)sulfinyl]acetamide that has R configuration at the sulfur atom. Like its racemate, modafinil, it is used for the treatment of sleeping disorders such as narcolepsy, obstructive sleep apnoea, and shift-work sleep disorder. Peak concentration in the blood later occurs later following administration than with modafinil, so it is thought that armodafinil may be more effective than modafinil in treating people with excessive daytime sleepiness.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C15H15NO2S
Net Charge 0
Average Mass 273.35000
Monoisotopic Mass 273.08235
InChI InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)/t19-/m1/s1
InChIKey YFGHCGITMMYXAQ-LJQANCHMSA-N
SMILES NC(=O)C[S@@](=O)C(c1ccccc1)c1ccccc1
Roles Classification
Application(s): central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
eugeroic
A phsychotropic drug that improves wakefulness and alertness, and reduces tiredness, drowsiness, and the need for sleep. Eugeroics are relatively non-addictive and are used in the treatment of narcolepsy and other sleep disorders.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing armodafinil (CHEBI:77590) has role central nervous system stimulant (CHEBI:35337)
armodafinil (CHEBI:77590) has role eugeroic (CHEBI:77567)
armodafinil (CHEBI:77590) is a 2-[(diphenylmethyl)sulfinyl]acetamide (CHEBI:77585)
armodafinil (CHEBI:77590) is enantiomer of (S)-modafinil (CHEBI:77591)
Incoming modafinil (CHEBI:31859) has part armodafinil (CHEBI:77590)
(S)-modafinil (CHEBI:77591) is enantiomer of armodafinil (CHEBI:77590)
IUPAC Name
2-[(R)-(diphenylmethyl)sulfinyl]acetamide
INNs Sources
armodafinil WHO MedNet
armodafinil WHO MedNet
armodafinilo WHO MedNet
armodafinilum WHO MedNet
Synonyms Sources
(−)-(R)-modafinil ChEBI
(−)-modafinil ChEBI
(R)-(−)-modafinil ChEBI
(R)-modafinil ChEBI
CEP 10953 ChemIDplus
CEP-10953 ChemIDplus
Brand Name Source
Nuvigil KEGG DRUG
Manual Xrefs Databases
4501 DrugCentral
Armodafinil Wikipedia
D03215 KEGG DRUG
View more database links
Registry Numbers Types Sources
112111-43-0 CAS Registry Number KEGG DRUG
112111-43-0 CAS Registry Number ChemIDplus
9767970 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19663523 PubMed citation Europe PMC
19689169 PubMed citation Europe PMC
20697340 PubMed citation Europe PMC
20816042 PubMed citation Europe PMC
21427431 PubMed citation Europe PMC
22039290 PubMed citation Europe PMC
22128728 PubMed citation Europe PMC
22210169 PubMed citation Europe PMC
22537794 PubMed citation Europe PMC
22803602 PubMed citation Europe PMC
22917711 PubMed citation Europe PMC
22960434 PubMed citation Europe PMC
22967783 PubMed citation Europe PMC
23251870 PubMed citation Europe PMC
23983964 PubMed citation Europe PMC
24122734 PubMed citation Europe PMC
Last Modified
22 February 2017