Modafinil sulfone

Modafinil sulfone (code name CRL-41056) is an achiral, oxidized metabolite of modafinil, a wakefulness-promoting agent. It is one of two major circulating metabolites of modafinil, the other being modafinil acid. Modafinil sulfone is also a metabolite of the modafinil prodrug, adrafinil. Modafinil sulfone is also a metabolite of armodafinil, the (R)-(–)-enantiomer of modafinil, as oxidation to the sulfone removes the chiral center at the sulfur atom. Modafinil sulfone has been described as inactive,^[1] and similarly to modafinil acid, does not appear to contribute to the wakefulness-promoting effects of modafinil.^[2][3][4] However, like modafinil, modafinil sulfone was found to show anticonvulsant properties in animals, indicating that it does possess some biological activity.^[5][6][7]

Modafinil sulfone

Names
Preferred IUPAC name 2-(Diphenylmethanesulfonyl)acetamide
Other names CRL-41056; Diphenylmethylsulfonylacetamide
Identifiers
CAS Number	118779-53-6 Y
3D model (JSmol)	Interactive image
ChemSpider	4962374
PubChem CID	6460146
UNII	946LME1J4S Y
CompTox Dashboard (EPA)	DTXSID10424213
InChI InChI=1S/C15H15NO3S/c16-14(17)11-20(18,19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17) Key: ZESNOWZYHYRSRY-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)(=O)CC(=O)N
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• List of modafinil analogues and derivatives