Armodafinil

Armodafinil
Clinical data
Trade names	Nuvigil, others
Other names	(R)-Modafinil; R-Modafinil; (R)-(–)-Modafinil; (–)-Modafinil; CRL-40982; CEP-10952
AHFS/Drugs.com	Monograph
MedlinePlus	a602016
Pregnancy; category	C;
Dependence; liability	Low
Routes of; administration	Oral (tablets)
Drug class	Atypical dopamine reuptake inhibitor; wakefulness-promoting agent
ATC code	N06BA13 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class B1 (Psychoactive drugs); US: Schedule IV;
Pharmacokinetic data
Bioavailability	Unknown (due to poor aqueous solubility; but modafinil is 40–65% based on urinary excretion)
Protein binding	Unknown (but for modafinil is moderate, primarily to albumin)
Metabolism	Liver, including CYP3A4 and other enzymes (hydrolytic amidation, sulfoxidation, aromatic ring hydroxylation, and glucuronide conjugation)
Metabolites	• Armodafinil acid; • Modafinil sulfone
Onset of action	1.5–6.5 h (range 0.5–11 h) (peak)
Elimination half-life	10–17 hours
Duration of action	Up to 13.5 hours
Excretion	Unknown (but modafinil is excreted 80% in urine and 1.0% in feces)
Identifiers
	IUPAC name (–)-2-[(R)-(diphenylmethyl)sulfinyl]acetamide;
CAS Number	112111-43-0 ;
PubChem CID	9690109;
ChemSpider	7962943 ;
UNII	V63XWA605I;
KEGG	D03215 ;
ChEBI	CHEBI:77590 ;
ChEMBL	ChEMBL1201192 ;
CompTox Dashboard (EPA)	DTXSID90920667 ;
ECHA InfoCard	100.207.833
Chemical and physical data
Formula	C15H15NO2S
Molar mass	273.35 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)[S@](=O)CC(=O)N;
	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 ; Key:YFGHCGITMMYXAQ-LJQANCHMSA-N ;
	(verify)

Armodafinil, sold under the brand name Nuvigil, is a wakefulness-promoting medication which is used to treat excessive daytime sleepiness associated with obstructive sleep apnea, narcolepsy, and shift work disorder. It is also used off-label for certain other indications. The drug is taken by mouth.

Side effects of armodafinil include headache, nausea, dizziness, and insomnia. Armodafinil acts as a selective atypical dopamine reuptake inhibitor (DRI) and hence as an indirect dopamine receptor agonist. However, other mechanisms might also be involved in its effects. Chemically, armodafinil is the enantiopure (R)-(–)-enantiomer of the racemic mixture modafinil (brand name Provigil). Both enantiomers of modafinil are active as DRIs and wakefulness-promoting agents, but armodafinil is more potent and longer-acting.

Armodafinil is produced by the pharmaceutical company Cephalon and was approved by the United States Food and Drug Administration (FDA) in 2007. In 2016, the FDA granted Mylan rights for the first generic version of armodafinil to be marketed in the United States.