Modafinil acid

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Modafinil acid
File:Modafinil acid.svg
Names
Preferred IUPAC name
(Diphenylmethanesulfinyl)acetic acid
Other names
Modafinilic acid; Modafinil carboxylate; CRL-40467
Identifiers
3D model (JSmol)
ChemSpider
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C15H14O3S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H,16,17)
    Key: QARQPIWTMBRJFX-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)O
Properties
C15H14O3S
Molar mass 274.33 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Modafinil acid (code name CRL-40467), also known as modafinilic acid or modafinil carboxylate, is one of the two major metabolites of modafinil – the other being modafinil sulfone.[1] Modafinil acid is also a metabolite of the modafinil prodrug, adrafinil, and the (R)-(–)-enantiomer is a metabolite of armodafinil, the (R)-(–)-enantiomer of modafinil.[2] Between 30 - 60% of modafinil is converted to modafinil acid and its half life is roughly half that of modafinil (about 7 hours).[3] Modafinil acid seems to be inactive,[4] and similarly to modafinil sulfone, does not appear to contribute to the wakefulness-promoting/psychostimulant effects of modafinil.[5][6][7]

In the breakdown process of modafinil, modafinil is primarily hydrolyzed by an esterase or amidase enzyme into modafinil acid.[8] The apparent clearance of modafinil acid is significantly higher than that of modafinil, following the hypothesis that metabolism increases the polarity and the clearance of modafinil.[9]

See also

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References

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