Adrafinil

Adrafinil
Clinical data
Trade names	Olmifon
Other names	CRL-40028
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06BX17 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.;
Pharmacokinetic data
Bioavailability	80%
Metabolism	75% (liver)
Metabolites	Modafinil
Elimination half-life	1 hour (T1/2 is 12–15 hours for modafinil)
Excretion	Kidney
Identifiers
	IUPAC name (±)-2-Benzhydrylsulfinylethanehydroxamic acid;
CAS Number	63547-13-7 ;
PubChem CID	3033226;
DrugBank	DB08925 ;
ChemSpider	2297976 ;
UNII	BI81Z4542G;
KEGG	D07348 ;
ChEMBL	ChEMBL93077 ;
CompTox Dashboard (EPA)	DTXSID4046498 ;
ECHA InfoCard	100.058.440
Chemical and physical data
Formula	C15H15NO3S
Molar mass	289.35 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(C(c1ccccc1)c2ccccc2)CC(=O)NO;
	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) ; Key:CGNMLOKEMNBUAI-UHFFFAOYSA-N ;
	(what is this?) (verify)

Adrafinil, sold under the brand name Olmifon, is a wakefulness-promoting medication that was formerly used in France to improve alertness, attention, wakefulness, and mood, particularly in the elderly.^[6]^[7]^[8] It was also used off-label by individuals who wished to avoid fatigue, such as night workers or others who needed to stay awake and alert for long periods of time. Additionally, the medication has been used non-medically as a novel vigilance-promoting agent.^[6]

Adrafinil is a prodrug; it is primarily metabolized in vivo to modafinil, resulting in very similar pharmacological effects.^[6] 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.^{[citation needed]}

Adrafinil was marketed in France until September 2011 when it was voluntarily discontinued due to an unfavorable risk–benefit ratio.^[7]

^ "Peak Nootropics LLC aka Advanced Nootropics - 557887 - 02/05/2019". Center for Food Safety and Applied Nutrition (CFSAN). U.S. Food and Drug Administration. 2019-12-20. Retrieved 2023-05-05.
^ Office of Regulatory Affairs (2019-12-20). "Hermitage Man Sentenced for Importing and Selling Drugs Not Approved by FDA". U.S. Department of Justice – via U.S. Food and Drug Administration.
^ "Fort Collins Couple Sentenced to Federal Prison for Illegally Selling Unapproved Drugs". Food and Drug Administration. FDA Office of Criminal Investigations. June 10, 2022. Retrieved May 21, 2023.
^ "Arizona Company and CEO Plead Guilty to the Distribution of Drugs Not Approved by the FDA and Will Pay $2.4 Million". Food and Drug Administration. FDA Office of Criminal Investigations. October 30, 2023. Retrieved November 6, 2023.
^ Robertson P, Hellriegel ET (2003). "Clinical pharmacokinetic profile of modafinil". Clin Pharmacokinet. 42 (2): 123–37. doi:10.2165/00003088-200342020-00002. PMID 12537513. S2CID 1266677.
^ ^a ^b ^c Milgram N (1999). "Adrafinil: A Novel Vigilance Promoting Agent". CNS Drug Reviews. 5 (3): 193–212. doi:10.1111/j.1527-3458.1999.tb00100.x.
^ ^a ^b AFSSAPS (2011). "Point d'information sur les dossiers discutés en commission d'AMM Séance du jeudi 1er décembre 2011 - Communiqué". Archived from the original on 13 September 2017.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 20–. ISBN 978-3-88763-075-1.

[CFSAN-1] "Peak Nootropics LLC aka Advanced Nootropics - 557887 - 02/05/2019". Center for Food Safety and Applied Nutrition (CFSAN). U.S. Food and Drug Administration. 2019-12-20. Retrieved 2023-05-05.

[ORA_2019-2] Office of Regulatory Affairs (2019-12-20). "Hermitage Man Sentenced for Importing and Selling Drugs Not Approved by FDA". U.S. Department of Justice – via U.S. Food and Drug Administration.

[OCI_2022-3] "Fort Collins Couple Sentenced to Federal Prison for Illegally Selling Unapproved Drugs". Food and Drug Administration. FDA Office of Criminal Investigations. June 10, 2022. Retrieved May 21, 2023.

[Arizona-4] "Arizona Company and CEO Plead Guilty to the Distribution of Drugs Not Approved by the FDA and Will Pay $2.4 Million". Food and Drug Administration. FDA Office of Criminal Investigations. October 30, 2023. Retrieved November 6, 2023.

[pmid12537513-5] Robertson P, Hellriegel ET (2003). "Clinical pharmacokinetic profile of modafinil". Clin Pharmacokinet. 42 (2): 123–37. doi:10.2165/00003088-200342020-00002. PMID 12537513. S2CID 1266677.

[Milgram2014-6] Milgram N (1999). "Adrafinil: A Novel Vigilance Promoting Agent". CNS Drug Reviews. 5 (3): 193–212. doi:10.1111/j.1527-3458.1999.tb00100.x.

[ANSM2011-7] AFSSAPS (2011). "Point d'information sur les dossiers discutés en commission d'AMM Séance du jeudi 1er décembre 2011 - Communiqué". Archived from the original on 13 September 2017.

[IndexNominum2000-8] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 20–. ISBN 978-3-88763-075-1.

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