Adrafinil

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Adrafinil
other names	( RS ) -2- (Benzhydrylsulfinyl) acetohydroxamic acid ( IUPAC ) ; (±) -2- (Benzhydrylsulfinyl) acetohydroxamic acid; CRL 40028;
Molecular formula	C 15 H 15 NO 3 S
Brief description	white solid
External identifiers / databases
EC number	264-303-1
ECHA InfoCard	100.058.440
PubChem	3033226
ChemSpider	2297976
DrugBank	DB08925
Wikidata	Q366482
Drug information
ATC code	N06 BX17
Drug class	Psychostimulant
properties
Molar mass	289.35 g · mol -1
solubility	soluble in DMSO (35 mg / mL)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	1950 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Adrafinil is a drug used to treat sleep disorders such as B. Narcolepsy . The substance belongs to a group of psychostimulating drugs that differ significantly in their molecular structure from the amphetamine- based stimulants .

Adrafinil is a prodrug that only becomes effective when it is metabolized to Modafinil . In its effect, it corresponds to Modafinil, but the effect is delayed due to the metabolism step. Like Modafinil, it is a prohibited doping substance .

Adrafinil was marketed in France from 1985 under the product name Olmifon ^® . After the French Medicines Agency announced the manufacturer Cephalon in April 2011 that it was planning a reassessment of the risk-benefit ratio of Olmifon , Cephalon ceased sales.

Stereoisomerism

Adrafinil is a sulfoxide and has a stereocenter on the sulfur atom, so it is chiral . The drug is used as a racemate , i.e. from a 1: 1 mixture of the ( R ) form and the mirror image of the ( S ) form.

Prescription Status

In Germany, Adrafinil does not require a prescription . There are no approved finished medicinal products in Germany, Austria or Switzerland.

Individual evidence

↑ ^a ^b ^c ^d ^e Data sheet Adrafinil ≥ 98% (HPLC), solid from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).
↑ The 2009 Prohibited List WORLD ANTI-DOPING CODE Valid 1 January 2009 ( Memento from July 19, 2014 in the Internet Archive ) (PDF; 177 kB).
↑ Point d'information sur les dossiers discutés en commission d'AMM Séance , December 2, 2011.
↑ Appendix 1 of the Medicinal Prescription Ordinance (AMVV).

Web links

MeSH Adrafinil

[Sigma-1] Data sheet Adrafinil ≥ 98% (HPLC), solid from Sigma-Aldrich , accessed on March 20, 2011 ( PDF ).

[2] The 2009 Prohibited List WORLD ANTI-DOPING CODE Valid 1 January 2009 ( Memento from July 19, 2014 in the Internet Archive ) (PDF; 177 kB).

[3] Point d'information sur les dossiers discutés en commission d'AMM Séance , December 2, 2011.

[4] Appendix 1 of the Medicinal Prescription Ordinance (AMVV).