Adrafinil

Adrafinil

Systematic (IUPAC) name
(RS)-2-benzhydrylsulfinylethanehydroxamic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Unscheduled (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	80%
Metabolism	75% Hepatic
Half-life	1 hour
Excretion	Renal
Identifiers
CAS number	63547-13-7 Y
ATC code	N06BX17
PubChem	CID 3033226
ChemSpider	2297976 Y
UNII	BI81Z4542G Y
KEGG	D07348 Y
ChEMBL	CHEMBL93077 Y
Chemical data
Formula	C15H15NO3S
Mol. mass	289.351 g/mol
SMILES	eMolecules & PubChem
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) Y Key:CGNMLOKEMNBUAI-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Adrafinil (CRL-40028, Olmifon) is a mild central nervous system stimulant drug used to relieve excessive sleepiness and inattention in elderly patients. It is also used off-label by individuals wishing to avoid fatigue, such as night workers or others who need to stay awake and alert for long periods of time.

Adrafinil is a prodrug; it is primarily metabolized in vivo to modafinil, resulting in nearly identical 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 does not currently have FDA approval and is thus unregulated in the United States. It was marketed in France and elsewhere in Europe under the trade name Olmifon until September 2011 when France's FDA equivalent reassessed the drug and withdrew marketing permission.^[1]

History

Adrafinil was discovered in the late 1970s by scientists working with the French pharmaceutical company Group Lafon. First offered in France in 1986 as an experimental treatment for narcolepsy, Lafon later developed modafinil, the primary metabolite of adrafinil. Modafinil possesses greater selective alpha-1 adrenergic activity than adrafinil without the side effects of stomach pain, skin irritations, feelings of tension^{[citation needed]}, and increases in liver enzyme levels.

It is important to monitor the liver of an individual using adrafinil. It can cause liver damage in some instances.

As of September 2011, Cephalon has discontinued the Olmifon product.^[1]

Legal status

Adrafinil and its close relative modafinil were added to the list of substances prohibited for athletic competition according to World Anti-Doping Agency in 2004.^[2]

In the United States, adrafinil is currently^[update] unregulated. It has not been approved for any clinical uses by the U.S. Food and Drug Administration. Unlike modafinil, adrafinil is not classified as a controlled substance and does not fall under DEA jurisdiction; in particular, it is not illegal to possess without a prescription and can be imported privately by citizens.

See also

• Ampakines
• CRL-40941
• Modafinil

References

External links

• "SID 184744 - PubChem Substance Summary". PubChem Project. National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=184744. Retrieved 7 December 2005. 
• "Adrafinil - Bank of Automated Data on Drugs". Bank of Automated Data on Drugs. VIDAL. Archived from the original on 5 October 2008. http://www2.biam2.org/www/Sub1545.html. Retrieved 4 October 2008. 
• "Adrafinil: A Novel Vigilance Promoting Agent" by Norton W. Milgram, Heather Callahan and Christina Siwak of the University of Toronto at Scarborough, CNS Drug Reviews, Vol. 5, No. 3, pp. 193–212 (PDF).
• "Adrafinil-induced Orofacial Dyskinesia" by S. Thobois, J. Xie, H. Mollion, I. Benatru and E. Broussolle of the Department of Neurology, Pierre Wertheimer Neurological Hospital, Lyon, France.