Adrafinil

Adrafinil

File:Adrafinil-structure.png
Clinical data
Routes of administration	Oral
ATC code	N06BX17 (WHO)
Identifiers
IUPAC name 2-benzhydrylsulfinylethanehydroxamic acid
CAS Number	63547-13-7
PubChem CID	3033226
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Molar mass	289.351 g/mol

Adrafinil 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 (Provigil®), 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, also known by the codename CRL 40028, has as its chemical name 2-(Diphenylmethyl) sulfinyl acetohydroxamic acid. Its molecular formula is C₁₅H₁₅NO₃S. The drug's molecular weight is 289.4 daltons.

Adrafinil does not currently have FDA approval in the United States, although it is used in France and elsewhere in Europe. The drug is marketed by the American pharmaceutical company Cephalon, which acquired Group Lafon in 2001, under the brand name Olmifon.

History

Adrafinil was discovered in the late 1970s by scientists working with the French pharmaceutical company Group Lafon. The drug was first offered as an experimental treatment for narcolepsy in France in 1986. Later on, Lafon scientists developed modafinil as a stand-alone drug because the latter drug was understood to be a more highly selective alpha-1 adrenergic and also featured less in the way of side effects such as stomach pain, skin irritations, feelings of tension, and an increase in liver enzyme levels.

Legal status

Adrafinil and its close relative modafinil were added to the list of prohibited substances according to World Anti-Doping Agency in 2004.

In United States, adrafinil is currently unregulated. It has not been approved for any clinical uses by the U.S. Food and Drug Administration. As such, it can't be legally sold or introduced into interstate commerce. Unlike modafinil, adrafinil is not yet classified as a controlled substance and does not fall under DEA jurisdiction; particularly, it is not illegal to possess without a prescription and can be imported privately by citizens.

Trivia

The metabolites of Adrafinil (as well as Modafinil) contain sulfur, and can easily be detected by a peculiar odour of the urine of the person who has taken it.

References

• "SID 184744 -- PubChem Substance Summary". The PubChem Project. National Center for Biotechnology Information.

See also

• Modafinil
• Ampakines

External links

• 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 Thobois S, Xie J, Mollion H, Benatru I, Broussolle E. of the Department of Neurology, The Pierre Wertheimer Neurological Hospital, Lyon, France