CHEBI:77590 - armodafinil

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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.
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Formula C15H15NO2S
Net Charge 0
Average Mass 273.35000
Monoisotopic Mass 273.082
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.
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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
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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
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Last Modified
22 February 2017