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
  • AU: S4 (Prescription only)
  • Unscheduled (US)
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability 80%
Metabolism 75% Hepatic, Cyp?
Biological half-life 1 hour
Excretion Renal
Identifiers
CAS Number 63547-13-7 N
ATC code N06BX17 (WHO)
PubChem CID: 3033226
DrugBank DB08925
ChemSpider 2297976 YesY
UNII BI81Z4542G YesY
KEGG D07348 YesY
ChEMBL CHEMBL93077 YesY
Synonyms CRL-40028
Chemical data
Formula C15H15NO3S
Molecular mass 289.351 g/mol
  • O=S(C(c1ccccc1)c2ccccc2)CC(=O)NO
  • 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) YesY
  • Key:CGNMLOKEMNBUAI-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Adrafinil (Olmifon) is a wakefulness-promoting agent (or eugeroic) 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, citing known adverse reactions and an unsatisfactory risk to benefit ratio.[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. Even though the exact mechanism of action is unclear, "most investigators assume that adrafinil and modafinil both serve as α1-adrenergic receptor agonists."[2] The evidence in support of this hypothesis is, however, weak and other mechanisms of action are probable.[2] Modafinil possesses greater selective α1-adrenergic activity than adrafinil, without many of adrafinil's common side effects (stomach pain, skin irritation, and anxiety).[3]

Group Lafon was acquired by Cephalon in 2001.[4] As of September 2011, Cephalon has discontinued Olmifon, its adrafinil product.

Society and culture

Legal status

Athletic doping

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.[5]

United States

In the United States, adrafinil is currently unregulated.[6] 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 legal to possess without a prescription and can be imported privately by citizens.

Canada

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

New Zealand

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."[7]

See also

References

  1. ↑ AFSSAPS Withdraws Marketing Support
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ url=http://www.bloomberg.com/research/stocks/private/snapshot.asp?privcapId=1366624
  5. ↑ World Anti-Doping Agency - 2007 Prohibited List
  6. ↑ url=https://www.erowid.org/smarts/adrafinil/adrafinil_law.shtml
  7. ↑ MCC Minutes Out of Session Meeting. Medsafe.govt.nz (2013-05-23). Retrieved on 2013-12-18.

External links

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  • Lua error in package.lua at line 80: module 'strict' not found. open access publication - free to read
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