Adrafinil
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Adrafinil
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| Systematic (IUPAC) name | |
| 2-benzhydrylsulfinylethanehydroxamic acid | |
| Identifiers | |
| CAS number | |
| ATC code | N06 |
| PubChem | |
| Chemical data | |
| Formula | C15H15NO3S |
| Mol. mass | 289.351 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | 80% |
| Metabolism | 75% Hepatic |
| Half life | 1 hour |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
Unscheduled (US) |
| Routes | Oral |
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 and is thus unregulated in the United States, although it is used in France and elsewhere in Europe. The drug is marketed under the brand name Olmifon by the American pharmaceutical company Cephalon, which acquired Group Lafon in 2001.
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[edit] 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, 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.
[edit] 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.[1]
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.[citation needed]
[edit] Usage detection
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.[citation needed]
[edit] References
- "SID 184744 -- PubChem Substance Summary". The PubChem Project. National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=184744. Retrieved on 7 December 2005.
- "Adrafinil -- Bank of Automated Data on Drugs". Bank of Automated Data on Drugs. VIDAL. http://www2.biam2.org/www/Sub1545.html. Retrieved on 4 October 2008.
[edit] See also
[edit] 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
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