Adrafinil

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Adrafinil
Adrafinil.svg
Systematic (IUPAC) name
(RS)-2-benzhydrylsulfinylethanehydroxamic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status Prescription Only (S4) (AU) Unscheduled (US)
Routes Oral
Pharmacokinetic data
Bioavailability 80%
Metabolism 75% Hepatic, Cyp?
Half-life 1 hour
Excretion Renal
Identifiers
CAS number 63547-13-7 N
ATC code N06BX17
PubChem CID 3033226
ChemSpider 2297976 YesY
UNII BI81Z4542G YesY
KEGG D07348 YesY
ChEMBL CHEMBL93077 YesY
Chemical data
Formula C15H15NO3S 
Mol. mass 289.351 g/mol
 N (what is this?)  (verify)

Adrafinil (CRL-40028, Olmifon) is a mild central nervous system stimulant drug used to relieve excessive sleepiness and inattention. 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.

History[edit]

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 many of adrafinil's common side-effects (stomach pain, skin irritation, anxiety and (with prolonged use) elevated liver enzymes).[1] This makes it important to monitor the liver of an individual using adrafinil for prolonged periods.

As of September 2011, Cephalon has discontinued the Olmifon product.

Legal status[edit]

Athletic doping[edit]

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

United States[edit]

In the United States, adrafinil is currently 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.

Canada[edit]

In Canada adrafinil is unregulated and can be legally purchased within the country as a research chemical, or imported privately by citizens.

New Zealand[edit]

In 2005 a Medical Classification Committee in New Zealand recommended to MEDSAFE NZ that Adrafinil be classified as a prescription medicine.

"Adrafinil had been referred to the MCC for classification as a prescription medicine by the Medicines Control section of Medsafe following growing concern about increased imports and potential abuse of this substance as a party drug. Evidence of misuse was supplied in support of the request for classification.

Adrafinil is not scheduled in New Zealand but is chemically related to modafinil which is a prescription medicine taken orally for mental function impairment in the elderly.

All participants agreed that adrafinil should be classified as a prescription medicine."[3]

See also[edit]

References[edit]

  1. ^ Ballas, Christos A; Deborah Kim; Claudia F Baldassano; Nicholas Hoeh (July 2002). "Modafinil: past, present and future". Expert Review of Neurotherapeutics 2 (4): 449–57. doi:10.1586/14737175.2.4.449. PMID 19810941. 
  2. ^ World Anti-Doping Agency - 2007 Prohibited List
  3. ^ MCC Minutes Out of Session Meeting. Medsafe.govt.nz (2013-05-23). Retrieved on 2013-12-18.

External links[edit]