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| Names | |
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Preferred IUPAC name
2-(Diphenylmethanesulfonyl)acetamide | |
| Other names
CRL-41056; Diphenylmethylsulfonylacetamide
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| Identifiers | |
3D model (
JSmol)
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| ChemSpider | |
PubChem
CID
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| UNII | |
CompTox Dashboard (
EPA)
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Modafinil side effects". Monday, 7 January 2019
 | This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it. |
|
| |
| Names | |
|---|---|
|
Preferred IUPAC name
2-(Diphenylmethanesulfonyl)acetamide | |
| Other names
CRL-41056; Diphenylmethylsulfonylacetamide
| |
| Identifiers | |
3D model (
JSmol)
|
|
| ChemSpider | |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Modafinil side effects". Monday, 7 January 2019
|
| This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it. |