Modafinil sulfone

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Modafinil sulfone
Names
Preferred IUPAC name
2-(Diphenylmethanesulfonyl)acetamide
Other names
CRL-41056; Diphenylmethylsulfonylacetamide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • 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).

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]

References

  1. ^ Wong YN, Wang L, Hartman L, Simcoe D, Chen Y, Laughton W, Eldon R, Markland C, Grebow P (1998). "Comparison of the Single-Dose Pharmacokinetics and Tolerability of Modafinil and Dextroamphetamine Administered Alone or in Combination in Healthy Male Volunteers". The Journal of Clinical Pharmacology. 38 (10): 971–978. doi:10.1002/j.1552-4604.1998.tb04395.x. ISSN 0091-2700. PMID 9807980. S2CID 32857213.
  2. ^ Schwertner HA, Kong SB (2005). "Determination of modafinil in plasma and urine by reversed phase high-performance liquid-chromatography". Journal of Pharmaceutical and Biomedical Analysis. 37 (3): 475–479. doi:10.1016/j.jpba.2004.11.014. ISSN 0731-7085. PMID 15740906.
  3. ^ Robertson P, Hellriegel ET (2003). "Clinical Pharmacokinetic Profile of Modafinil". Clinical Pharmacokinetics. 42 (2): 123–137. doi:10.2165/00003088-200342020-00002. ISSN 0312-5963. PMID 12537513. S2CID 1266677.
  4. ^ Robertson P (2002). "Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers". Clinical Pharmacology & Therapeutics. 71 (1): 46–56. doi:10.1067/mcp.2002.121217. ISSN 0009-9236. PMID 11823757. S2CID 21552865.
  5. ^ Chatterjie N, Stables JP, Wang H, Alexander GJ (2004). "Anti-narcoleptic agent modafinil and its sulfone: a novel facile synthesis and potential anti-epileptic activity". Neurochem. Res. 29 (8): 1481–6. doi:10.1023/b:nere.0000029559.20581.1a. PMID 15260124. S2CID 956077.
  6. ^ "Modafinil side effects". Monday, 7 January 2019
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