Armodafinil

Structural formula
General
Non-proprietary name	Armodafinil
other names	( R ) -2 - [(Diphenylmethyl) sulfinyl] acetamide ( IUPAC ); ( R ) - (-) - 2 - [(Diphenylmethyl) sulfinyl] acetamide;
Molecular formula	C 15 H 15 NO 2 S
External identifiers / databases
EC number	682-508-8
ECHA InfoCard	100.207.833
PubChem	9690109
ChemSpider	7962943
DrugBank	DB06413
Wikidata	Q418913
Drug information
ATC code	N06 BA
Drug class	Psychostimulant
properties
Molar mass	273.35 g · mol -1
Physical state	firmly
Melting point	158-159 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 318
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Armodafinil is a drug from the group of psychostimulants that differs significantly from amphetamine- based stimulants in its molecular structure . It represents the ( R ) -enantiomer of the racemate Modafinil .

Armodafinil was developed by the pharmaceutical company Cephalon around 2004 . It received FDA approval on June 15, 2007 and was launched on the US market a little later as Nuvigil ^® . The substance is protected by a US patent until 2023.

Clinical information

application areas

The drug is approved in the USA for the treatment of excessive daytime sleepiness in patients aged 18 and over in connection with obstructive sleep apnea syndrome (OSAS), narcolepsy or shiftworker syndrome.

Interactions

Armodafinil is metabolized via cytochrome P450 3A4 and also inhibits certain subtypes of the cytochrome P450 enzyme family. There is the possibility of interactions with numerous other drugs, which in turn either inhibit or are metabolized by the same cytochrome P450 subtypes. These include, in particular, oral contraceptives , drugs for the treatment of seizure disorders ( anticonvulsants ), anti-coagulants ( anticoagulants ), antidepressants or the immunosuppressant cyclosporine .

Side effects

The most common side effects observed were: headache, nausea, dizziness, sleep disorders. Armodafinil can cause mild allergic reactions such as skin rashes or hay fever. Serious allergic skin reactions such as those observed with the racemic form modafinil, including Stevens-Johnson syndrome , cannot be excluded and treatment must be stopped immediately.

pharmacology

Mechanism of action

Armodafinil increases the state of wakefulness in patients who experience excessive sleepiness. It works by influencing certain neurotransmitter receptors and stimulating the sympathetic nervous system . As with Modafinil, the exact mechanism of action is unknown. In vitro , neither a direct nor an indirect effect as an α ₁ adrenoceptor or dopamine receptor agonist could be demonstrated. Armodafinil's ability to maintain wakefulness is similar to that of amphetamine , although it differs from them in its pharmacological profile.

Metabolism

The half-lives of the two enantiomers of Modafinil differ by a factor of three. The pharmacokinetics of armodafinil are dose-independent and linear in the range 50 to 400 mg. The active ingredient is quickly absorbed and metabolized in the liver to two main metabolites. Armodafinil and its metabolites are mainly eliminated via the kidneys. The dose should be reduced in patients with severe hepatic or renal insufficiency.

Individual evidence

↑ Osorio-Lozada, A .; Prisinzano, T .; Olivo, F .: Synthesis and determination of the absolute stereochemistry of the enantiomers of afrafinil and modafinil ; Tetrahedron Asymmetry 15 (2004) 3811-3815 doi : 10.1016 / j.tetasy.2004.10.019 .
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (-) - 2R - [(diphenylmethyl) sulfinyl] acetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 17, 2019, is reproduced from a self-classification by the distributor .
↑ Jörg Auf dem Hövel: Brain doping: eyes straight Telepolis, October 23, 2007.
↑ ^a ^b ^c ^d FDA Approved Labeling Text for Nuvigil (armodafinil) Tablets (PDF file; 523 kB).

literature

Patent US2006135621 : Method for the production of crystalline forms of optical enantiomers of modafinil. Published June 22, 2006 . ‌

Web links

Nuvigil (armodafinil) at RxList

[Asymetry2004-1] Osorio-Lozada, A .; Prisinzano, T .; Olivo, F .: Synthesis and determination of the absolute stereochemistry of the enantiomers of afrafinil and modafinil ; Tetrahedron Asymmetry 15 (2004) 3811-3815 doi : 10.1016 / j.tetasy.2004.10.019 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (-) - 2R - [(diphenylmethyl) sulfinyl] acetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 17, 2019, is reproduced from a self-classification by the distributor .

[T-2007-10-23-3] Jörg Auf dem Hövel: Brain doping: eyes straight Telepolis, October 23, 2007.

[labtext-4] FDA Approved Labeling Text for Nuvigil (armodafinil) Tablets (PDF file; 523 kB).