Adrafinil

Adrafinil
Clinical data
Trade names	Olmifon
Other names	CRL-40028; N-Hydroxymodafinil
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06BX17 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: Unapproved drug; use in dietary supplements, food, or medicine is unlawful.;
Pharmacokinetic data
Bioavailability	80%
Metabolism	75% (liver)
Metabolites	Modafinil
Elimination half-life	1 hour (T1/2 is 12–15 hours for modafinil)
Excretion	Kidney
Identifiers
	IUPAC name (±)-2-Benzhydrylsulfinylethanehydroxamic acid;
CAS Number	63547-13-7 ;
PubChem CID	3033226;
DrugBank	DB08925 ;
ChemSpider	2297976 ;
UNII	BI81Z4542G;
KEGG	D07348 ;
ChEMBL	ChEMBL93077 ;
CompTox Dashboard (EPA)	DTXSID4046498 ;
ECHA InfoCard	100.058.440
Chemical and physical data
Formula	C15H15NO3S
Molar mass	289.35 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(C(c1ccccc1)c2ccccc2)CC(=O)NO;
	InChI InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17) ; Key:CGNMLOKEMNBUAI-UHFFFAOYSA-N ;
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Adrafinil, sold under the brand name Olmifon, is a wakefulness-promoting medication that was formerly used in France to improve alertness, attention, wakefulness, and mood, particularly in the elderly. It was also used off-label by individuals who wished to avoid fatigue, such as night workers or others who needed to stay awake and alert for long periods of time. Additionally, the medication has been used non-medically as a novel vigilance-promoting agent.

Adrafinil is a prodrug; it is primarily metabolized in vivo to modafinil, resulting in very similar pharmacological effects. Unlike modafinil, however, it takes time for the metabolite to accumulate to active levels in the bloodstream. Effects usually are apparent within 45–60 minutes when taken orally on an empty stomach.

Adrafinil was marketed in France until September 2011 when it was voluntarily discontinued due to an unfavorable risk–benefit ratio.