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Modafinil sulfone

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Modafinil sulfone
Names
Preferred IUPAC name 2-(Diphenylmethanesulfonyl)acetamide
Other names CRL-41056; Diphenylmethylsulfonylacetamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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 , 100 kPa). Infobox references
Chemical compound

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, and similarly to modafinil acid, does not appear to contribute to the wakefulness-promoting effects of modafinil. However, like modafinil, modafinil sulfone was found to show anticonvulsant properties in animals, indicating that it does possess some biological activity.

See also

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
  7. "Provigil Online Pharmacy".16 January 2023
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