Chemistry:Modafinil acid
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| Names | |
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| Preferred IUPAC name
(Diphenylmethanesulfinyl)acetic acid | |
| Other names
Modafinilic acid; Modafinil carboxylate; CRL-40467
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
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| 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). | |
| Infobox references | |
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]
References
- ↑ "A novel study of screening and confirmation of modafinil, adrafinil and their metabolite modafinilic acid under EI-GC-MS and ESI-LC-MS-MS ionization". Indian Journal of Pharmacology 41 (6): 278–283. December 2009. doi:10.4103/0253-7613.59928. PMID 20407560.
- ↑ "Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil: Relevant clinical and forensic aspects". Substance Abuse 41 (2): 155–173. 2020. doi:10.1080/08897077.2019.1700584. PMID 31951804.
- ↑ "Open-label, single-dose pharmacokinetic study of modafinil tablets: influence of age and gender in normal subjects". Journal of Clinical Pharmacology 39 (3): 281–288. March 1999. doi:10.1177/009127009903900312. PMID 10073328.
- ↑ "Comparison of the single-dose pharmacokinetics and tolerability of modafinil and dextroamphetamine administered alone or in combination in healthy male volunteers". Journal of Clinical Pharmacology 38 (10): 971–978. October 1998. doi:10.1002/j.1552-4604.1998.tb04395.x. PMID 9807980.
- ↑ "Determination of modafinil in plasma and urine by reversed phase high-performance liquid-chromatography". Journal of Pharmaceutical and Biomedical Analysis 37 (3): 475–479. March 2005. doi:10.1016/j.jpba.2004.11.014. PMID 15740906. https://zenodo.org/record/1259161.
- ↑ "Clinical pharmacokinetic profile of modafinil". Clinical Pharmacokinetics 42 (2): 123–137. 2003. doi:10.2165/00003088-200342020-00002. PMID 12537513.
- ↑ "Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers". Clinical Pharmacology and Therapeutics 71 (1): 46–56. January 2002. doi:10.1067/mcp.2002.121217. PMID 11823757.
- ↑ "Population pharmacokinetics of modafinil acid and estimation of the metabolic conversion of modafinil into modafinil acid in 5 major ethnic groups of China". Acta Pharmacologica Sinica 33 (11): 1401–1408. November 2012. doi:10.1038/aps.2012.124. PMID 23103618.
- ↑ "Modafinil As A Physical Performance Enhancer" (in en-US). http://www.brainsupplements.co.uk/modafinil-physical-performance-enhancer/.
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